Longboat Key Vacation Rentals

(58 rentals)
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Longboat Key Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

$223

avg/night

$223
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Cedars East (0.6 mile walk) offers monthly memberships for tennis/pool/fitness center. The kitchen and bathrooms were remodeled in 2023. Appliances, cabinets, sectional sofa with sleeper and Roku TV's are all new (2023). The living area, kitchen and half bathroom are downstaris. Upstairs is the ...

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Property Type

Longboat Key Townhome

Featured review

"Highly recommend!!"

We just spent 2 months at Tim’s condo and can’t speak highly enough about it! The location is perfect, mid island, walk to beach, on the canal which is just beautiful!! It’s great to have 2 floors ...

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Condo

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Longboat Key Apartment | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$276

avg/night

$276
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 7th floor Islander Club condo was completely rebuilt in 2016 by the project of renowned Boston designer. Modern kitchen with stainless steel brand new appliances opens to spacious living room/dining area with oversized sofa and 55-inch HDTV. Master bedroom with king size bed offers beautiful view ...

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Property Type

Longboat Key Apartment

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Longboat Key Apartment
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$272

avg/night

$272
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy seeing sunrise from the lanai or on the dock, and also enjoy sunset on the beach, directly across the street. The unit is completely renovated, nicely furnished, and well stocked - designed for those who love to cook. This 2 bedroom, 2 bath first floor unit with fantastic bayou views its located ...

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Property Type

Longboat Key Apartment

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Longboat Key Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Distance to beach: 0.3 miles to Gulf Of Mexico

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Bring your boat or just enjoy the view of the canal in this coastal townhome! It’s on the North end of LBK on a deep water canal with quick access to Sarasota Bay and the Gulf of Mexico. The location is ideal near Harry’s Restaurant and Store and just steps from the Deeded Beach Front, Durante ...

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Property Type

Longboat Key Townhome

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Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 200 yards to Private Deeded Beach Access

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

*** CONTACT OWNER FOR: - rates are now reduced for off season months August -October 2024 & Discount for multi months rentals. ***A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short 3 minutes walk (200 meters) ...

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Property Type

Longboat Key House

Featured review

"Great house on LBK"

I have been coming to LBK for over 20 years. This was the best month I’ve spent on the island. The canal house is in a great location mid island with a short stroll to the beach. A variety of restaurants ...

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Longboat Key Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$378

avg/night

$378
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.Beautiful beachview unit on the 2nd floor with lake view ...

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$312

avg/night

$312
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse condo located on the 15th floor of Islands West Complex. You will love the beach views and fast Wi-Fi. Master bedroom with King bed has amazing views of the Bay and the Sarasota Downtown ...

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Property Type

Longboat Key Condo

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Longboat Key Apartment | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
1 review

$345

avg/night

$345
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Apartment

Featured review

"Great Rental"

Zilli 202 was the best rental! It had an absolutely gorgeous view. My husband and I went for our 35th anniversary. We could not have asked for a better place. Jim was a great host. He was very informative ...

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Longboat Key Apartment | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom

$368

avg/night

$368
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifacts, 40 year old flooring, one SIZE fits all, etc.). We call it ...

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Property Type

Longboat Key Apartment

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$441

avg/night

$441
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

7th floor corner unit with balcony offering wide, sweeping view of the beach and Gulf. Both bedrooms offer clear view of Bay and downtown Sarasota. The unit has been newly updated and professionally decorated complete with tile floors, quartz countertops, high end furnishings and remote blinds. Living ...

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Property Type

Longboat Key Condo

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Longboat Key Villa | On the beach
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
1 review

$552

avg/night

$552
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacations, the house was completely redecorated and stocked to offer all the comforts of home to our guests. A cool, beachy palette welcomes you to sit back and relax.Make plans now to ...

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Property Type

Longboat Key Villa

Featured review

"Spacious luxury right on the beach"

The owner is attentive to details and is there for you if you need him. Large, contemporary furnishings, private, full of amenities you desire and often don't get at a resort. Don't hesitate to rent this ...

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Longboat Key Villa
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom
5 reviews

$195

avg/night

$195
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly remodeled charming 2 bed/ 1 bath beach condo located 5 min walk from beach, restaurants, groceries and more. Perfect place for a relaxing beach getaway!Nestled in a quiet residential complex and centrally located in Longboat key, condo features a fully equipped renewed kitchen with upgraded ...

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Property Type

Longboat Key Villa

Featured review

"Little bit of paradise"

This is a darling condo, that looks exactly as it is pictured, with all the needed items for cooking and beaching and enjoying a a very relaxing vacation. August is not the best month in Florida but the ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$433

avg/night

$433
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

This is a Walkdown level fully remodeled condo. On the soft white sand beaches of Longboat Key, Beach Place offers 31 luxury acres and 1450 linear feet of beach. Resort Style Amenities include large community pool and exercise facility.New Listing! Perfect beach view elevated walkdown level fully ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$642

avg/night

$642
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

PENTHOUSE, DOUBLE BALCONIES, breathtaking wide sweeping straight on views of the Gulf and Bay make our Beachplace condo a true paradise on Longboat Key. This sought after resort is gated on the south end of the island close to the famous Saint Armands Circle, Publix’s and many highly rated restaurants. ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Longboat Key Beach - Condo is on the beach!

$262

avg/night

$262
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Beachcomber building and heated pool are located directly on the white sandy beach of Longboat Key! Suite 501 has an island view of Longboat Key with a partial view of Sarasota Bay from the 5th floor. Unit 501 is located ten steps to the elevator and 10 steps to the heated pool located directly on ...

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Property Type

Longboat Key Condo

Featured review

"Great vacation"

Great location and staff,very clean and comfortable.Being on beach store was across street.Very quite at night so glad we didn't stay at Anna Marie Island to busy.Staff very professional, getting back to ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$403

avg/night

$403
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. The sunsets are breathtaking. You will love the beach views and fast Wi-Fi. This is a luxury rental. Condo has a single unit washer/dryer in one. There is a Islands West is the ideal ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$257

avg/night

$257
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

60 Day Minimum Required. Beachfront Condo offers great views to the gulf from the 7th floor living room and bedroom. This unit is freshly remodeled. Enjoy the oversized balcony with two ceiling fans as you relax and watch the full beauty of nature.Association requires a minimum of 60 days. Direct ...

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Property Type

Longboat Key Condo

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Longboat Key Apartment | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
2 reviews

$310

avg/night

$310
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Apartment

Featured review

"Zilli’s Unit 201"

We did enjoy our stay at unit 201 and we mostly appreciated M. Zilli’s concerns and grand availability to make our stay comfortable and most enjoyable. M. Zilli is the owner and It was reassuring to ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$425

avg/night

$425
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Live life on the beach---Private parking included!Beachplace is one of Longboat Key's premier vacation rental locations on the island!With amazing direct Gulf-front views, this sophisticated and chic 4th floor condo with balcony has it all!This condo has modern updates throughout including ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$368

avg/night

$368
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful beachfront unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors.The online ...

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Property Type

Longboat Key Condo

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Longboat Key House
3 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 3 bedrooms, 2 bathrooms
2 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Surrounded by tropical landscaping & fruit trees, this cozy ranch features an open layout w/new kitchen! House features 3 real bedrooms, 2 full bathrooms, ample closet space. Enjoy a quiet retreat & fishpond & fire pit & Island living walking distance to Whitney Beach, 2 blocks to kayak/bay. ...

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Property Type

Longboat Key House

Featured review

"Island paradise, Island hideaway!"

I was lucky enough to nab this cute cottage for a month in November, I was looking for somewhere quiet to work and this place was fabulous. Situated on a quiet coconut palmed street with restaurants at ...

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Longboat Key Villa
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 150 yards to Gulf Of Mexico

$143

avg/night

$143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground Floor Villa Condo- 1 Bedroom- Sleeps 2 - walk 4 min to beachBeautiful end unit attached villa in the charming walkable community of St. Judes on Longboat Key. Just a short 4 minute walk to the private beach access and a 3 minute walk to the 32 acre Joan Durante Park FULL of fabulous tropical ...

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Property Type

Longboat Key Villa

Featured review

"Slice of paradise"

This place was clean and had everything you would need. The bed was the most comfortable bed I have ever slept in. The beautiful beach was just a short walk away and they provided beach chairs too. The ...

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$394

avg/night

$394
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Steps away from the longest stretch of private beach on Longboat Key and located on 30 acres of manicured grounds, Beachplace is one of the island’s most beautiful ...

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Property Type

Longboat Key Condo

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Longboat Key Villa
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 500 yards to Gulf of Mexico

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Little Palm on the bay in Longboat Key, Florida, a place to go when you want to relax and enjoy! Sunbathing, fishing, and boating right at your backdoor with the beach and pool only a short walk away!  BOATERS, you can bring your boat or rent a boat to be available right out your back door. Don’t ...

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Property Type

Longboat Key Villa

Featured review

"Nice trip"

I loved my month here. I would never have 5 people though. It is 600 sq. ft and 1 bath. There were two of us and it was fine. Lovely back area on a canal. Very quiet and nice people around. There ...

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.1 miles to Across Gulf of Mexico Dr

$171

avg/night

$171
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

TOTAL FULL DIRECT BAY VIEW in the front and Canal view in the back!!!! This 2 BR 2 BATH comfortable coastal beachy condo will delight and impress both inside and out. The primary bedroom has a king bed and en-suite and the 2nd bedroom has a queen size bed. Previous reviews have all been 5 star on other ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

For those who do not know Beachplace, it is more of a resort than it is a gated condo community. During the winter there are plenty of planned activities including a movie night once a week, a book club, pot luck dinners, tennis, pickle ball and more. This beautiful 5th floor corner unit has amazing ...

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Property Type

Longboat Key Condo

Featured review

"Amazing Place"

Arrived on the 1st of May what amazing place the Beachplace is right on the Gulf of Mexico the beach and the water was amazing. So many restaurants to visit and a Publix just down the road . Can’t recommend ...

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
1 review

$358

avg/night

$358
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gulf side paradise with hundreds feet of beautiful beach. This one bedroom condo on the fourth floor with a private balcony is the place to enjoy the sound of the rolling waves and some of the most spectacular sunsets on Longboat Key. Take the elevator and you’re just steps away from the heated ...

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Property Type

Longboat Key Condo

Featured review

"Turtle Crawl Inn Resort Unit 402"

The unit was comfortable and the beach front view was spectacular. The property was also clean and very quiet. The office manager, Rebecca, was friendly and helpful. My husband and I would be delighted ...

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Longboat Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$522

avg/night

$522
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and walk trails and bay lookouts nearby. EASY ACCESS VIA a new, fully enclosed ELEVATOR, beside the GARAGE TO ALL THE LIVING AREAS! Over an acre of lawns joining to 35 acres of park ...

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Property Type

Longboat Key House

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Longboat Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 50 yards to Our own private beach!

$365

avg/night

$365
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Relax in this privately owned, Old Florida Charm, “coastal themed” ground floor condo located on the Southern Gulf side of Florida. The condo offers views of the Sarasota Bay, a community heated pool, hot tub, boat dock, and a three minute walk to the private beach with turquoise waters on ...

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Property Type

Longboat Key Condo

Featured review

"Vacation in paradise"

Wir hatten eine tolle Zeit auf Longboatkey, das zweite Mal, Aber dieses Mal mit direktem Strandzugang und einem atemberaubenden Sonnenaufgang an der Bay. Mit einem Kaffee Manatees und Delphine beobachten, ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$306

avg/night

$306
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This Spectacular beachfront condo on Longboat Key is a 2 bedroom, 2 bath unit on the 6th floor of the Arbomar Condominium. An open concept floor plan includes a galley kitchen with SubZero appliances, dining room, and living room that exits to a spacious lanai overlooking the Gulf of Mexico. Take in ...

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Property Type

Longboat Key Condo

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Longboat Key Cottage
1 BR | 1 BA | Sleeps 1 | Quick View
Sleeps 1, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Nestled in a serene enclave, this charming one-bedroom cottage is the perfect island oasis. Combining timeless elegance with modern amenities, it features high vaulted ceilings, a contemporary kitchen, & cutting-edge conveniences including high-speed internet, a reverse osmosis water system, & ...

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Property Type

Longboat Key Cottage

Featured review

"Cozy Coastal Cottage with EVERYTHING you need"

We had an unforgettable time in Longboat Key! The cottage we stayed in was perfect for what we were looking for. It’s located directly in between the bay and the gulf where we could easily walk from ...

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Views from every window 2 Bedroom/2 Bathroom (no one living above) corner end unit with access to a rooftop deck directly above this sunny and bright unobstructed panoramic view of Sarasota Bay with deeded beach access to one of the most pristine stretches of pearly white Gulf of Mexico sand directly ...

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Property Type

Longboat Key Condo

Featured review

"HBC"

Lovely place with a great view of the bay. Well set up with all of the things you need. Owner very accomodating

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Longboat Key Cottage
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Last minute fall getaway special!Just a short 0.3-mile stroll to Whitney Beach! This charmingly renovated cottage is tucked away in the back corner of a spacious, gated lot. Ideal for a romantic getaway for two: queen Tempurpedic sofa (no uncomfortable mattress bars!) and a cozy daybed to also accommodate ...

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Property Type

Longboat Key Cottage

Featured review

"Best Ideal Situation I could Have Hoped For"

I traveled cross country from Oregon and had no idea anything about Florida! I booked this place randomly without ever having been to this area or the East coast. Thank god it turned out the way it did! ...

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Longboat Key Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 500 feet to Private access

$179

avg/night

$179
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Private BEACH Access! [2 Units Available Turquoise Gem and Turtle Walk CONTACT ME Turtle Walk MAY BE AVAILABLE] *Designer Renovation* Single level, 4 minute Walk to Bright White Quartz Sand, Welcome to UPGRADED BEACH PARADISE Featuring - NEW Full Stainless-Steel Kitchen, NEW Cabinets and Granite Countertops. ...

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Property Type

Longboat Key Apartment

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Longboat Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$566

avg/night

$566
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for ...

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Property Type

Longboat Key House

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$270

avg/night

$270
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated 2 bedroom, 2 bath condo. Open kitchen, spacious living room and an integrated dining room. Bonus room which can serve as an office or extra sleeping quarter. Master bedroom features a private balcony to enjoy the ocean and spectacular sunsets. Laundry room with full size washer and dryer. ...

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
11 reviews
last minute deal
LAST MINUTE DEAL 11/6 - 11/20: Beachfront with panoramic Gulf and sunsets views. Great reviews on all paid platforms. Ocean Views!

$328

avg/night

$328
avg per night
Offer for: Nov 6 - Nov 20:
Beachfront with panoramic Gulf and sunsets views. Great reviews on all paid platforms. Ocean Views!

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

NO HURRICANE HELENE AND MILTON DAMAGES! GULF FRONT - ON THE SAND. SPECTACULAR GULF VIEWS AND SUNSET VISTAS. JUST RENOVATED WITH NEW BATHROOM AND NEW FLOORING!RATES ARE SUBJECT TO CHANGE WITHOUT UPDATING ON THIS PLATFORM. CAN BE LOWER OR HIGHER. PLEASE REQUEST. AVAILABLITY ON CALENDAR MIGHT NOT ...

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Property Type

Longboat Key Condo

Featured review

"Perfect!"

Complex was well maintained and managed. Our unit had beachfront views with stunning sunsets. Everything we needed was provided. During our visit it wasn't crowded or noisy so very relaxing place to unwind ...

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DEAL
Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Whitney Beach

$228

avg/night

$228
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

3 bedroom, 2 bath cottage close to Gulf and Bay Great 3 bedroom, 2 bath house with pool on the north end of Longboat Key. Longbeach Village is a neighborhood with 'Old Florida Charm' unlike most of LBK. You will be two houses from the bay (boat launch and pier), and 3 blocks from a fabulous ...

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Property Type

Longboat Key House

Featured review

"Sunny Beaches"

Quiet place, close to beaches and restaurants. …..

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Longboat Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$264

avg/night

$264
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Looking to step back in time to enjoy the "Old Florida Lifestyle?" Located in the quaint historic village of Longbeach is this cozy one-family house with two queen bedrooms and a third private space that sleeps two more. Two fulls baths accommodates all. Kitchen includes microwave, coffee ...

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Property Type

Longboat Key House

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$255

avg/night

$255
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning JUNE 6, 2024.Bayport Beach and Tennis Club is a beach to bay tropical oasis situated on 27 lushly landscaped acres on Longboat Key, FL. The grounds are meticulously maintained and provide a tranquil and ...

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Property Type

Longboat Key Condo

Featured review

"Home Away From Home"

The property owners are terrific. The apartment was impeccable and met all needs and beyond. Would definitely return

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Longboat Key - you've stumbled on a unique hidden gem tucked away on the upper Gulf Coast of Florida. Small, private, and quiet - the key vacation that really makes you get away from it all. Our condominium in Bayport Beach and Tennis Club is a beautiful private retreat with unobstructed ...

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Property Type

Longboat Key Condo

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Longboat Key Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$167

avg/night

$167
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Available now! Beautiful. Newly remodeled condo with spectacular views of Sarasota Bay and private access to the white sand beaches across the street (few steps away). Second floor, end unit located in Pelican Harbour Condominium and Beach Club in Longboat Key. An extensive remodel was just completed ...

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Property Type

Longboat Key Apartment

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 5 feet to Just outside your door & window

$267

avg/night

$267
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful!No need to fight any traffic or an overcrowded public beach. Beautiful view of the turquoise waters of the Gulf of Mexico. It is very private and peaceful. The ideal spot for a relaxing getaway ...

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Property Type

Longboat Key Condo

Featured review

"Happy in Longboat Key"

We enjoyed our stay & owners were very helpful for helping us when needed! Beautiful view of the Gulf! Unit was sparkling clean & well equipped & comfortable. We are returning next year as well. The property ...

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Welcome to your amazing beachfront vacation. The apartment has a fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room ...

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Property Type

Longboat Key Condo

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Longboat Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.1 miles to Private beach

$234

avg/night

$234
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This WATERFRONT condo is very spacious, beautifully updated. Perfectly located within a minute of a private sandy beach and right along the waters edge of a salt water canal and intra coastal waterway. Enjoy the great water views that span the full width of the ground floor condo. Fishing, kayaking, ...

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Property Type

Longboat Key Condo

Featured review

"Absolutely wonderful - wish we could go back!!"

First, we have vacationed on Longboat for the past 5 years. Longboat is a special place where you feel relaxed, enjoy the gorgeous beach and the laid back feel compared to more touristy places in Florida. ...

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Longboat Key House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

$190

avg/night

$190
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Charming one-bedroom guest house featuring floor-to-ceiling windows, high vaulted ceilings, & an open kitchen. Balcony enclosed with heavy curtains, perfect for peaceful mornings & nights. Kick back, relax in this calm, stylish space, capturing the essence of Old Florida. Experience peaceful island ...

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Property Type

Longboat Key House

Featured review

"Amazing Location"

This place is amazing. The location could not be more perfect. The beach and three amazing restaurants are all within five minutes walking distance. The grounds are impeccably kept and the owner is very ...

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Longboat Key Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Situated on Longboat Key, this secured and gated 1st floor NEWLY RENOVATED condo boasts water views throughout, 2 spacious lanai, each with own walk-down steps to water and pool, across the street to private beach with cabanas, grills, restrooms, etc. Great room, fully equipped kitchen (including microwave, ...

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Property Type

Longboat Key Condo

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Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Discover a unique, remodeled 1920s bungalow near Whitney Beach and the bay, offering an open layout with high ceilings and modern appliances. This home features a heated pool, hot tub, and lush, private landscaping. Originally a post office, it has historical charm with a fully fenced yard, boat parking. ...

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Property Type

Longboat Key House

Featured review

"Mini Paradise on LBK"

We stayed at this gem for 6 weeks while renovating our home and it was fabulous!!! The location is amazing, literally 3 blocks from Whitney Beach, fabulous dining options literally across the street (Mar ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

You will be captivated by the majestic ocean views the moment you step foot into the unit. Step out of this 1st floor unit and in just over 100 steps you be dipping your toes in the water. Whitney beach is pristine and private with wonderful people who own and rent. Enjoy the beachside pool and 4 ...

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Property Type

Longboat Key Condo

Featured review

"Great place"

Wonderful. Great location. Great facilities. Well equipped. Wonderful for families. Beach is gorgeous.

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Longboat Key Vacation Rentals

Longboat Key Weather

 | 

7222°  5111°
JANUARY
Ocean 6418°
7423°  5312°
FEBRUARY
Ocean 6518°
7725°  5714°
MARCH
Ocean 6719°
8228°  6016°
APRIL
Ocean 7323°
8731°  6518°
MAY
Ocean 7826°
9032°  7122°
JUNE
Ocean 8228°
9133°  7323°
JULY
Ocean 8530°
9133°  7323°
AUGUST
Ocean 8730°
9032°  7222°
SEPTEMBER
Ocean 8529°
8529°  6518°
OCTOBER
Ocean 8228°
8027°  5915°
NOVEMBER
Ocean 7524°
7423°  5312°
DECEMBER
Ocean 6921°

Escape to the Stunning Southwest Florida Shores with Longboat Key Condos for Rent


If you’re looking for some rest and relaxation after a tough few months at work or a long school year, Longboat Key vacation rentals are where it's at! As soon as your feet hit the sand and you feel the sun on your skin, the stress will begin to melt away.

Southwest Florida is home to so many unique and scenic beach towns. Some of them are small and sleepy, others are lively and energetic, and many more have an inviting mix of both. Are you unsure of where along the Florida coast to book your next vacation? As you deliberate, make sure to keep Longboat Key on your radar.

Longboat Key is a small, tight-knit community located on one of western Florida’s many barrier islands. To the east of Longboat Key is Sarasota Bay, and to the west is the expansive Gulf of Mexico. Thus, no matter where you are on Longboat Key, you’re sure to have a gorgeous view of the water and a short walk to the beach.

As you’re planning your beachside vacation in Longboat Key, you might be wondering whether to book a hotel for your lodging or choose something a bit more special. At FloridaRentals, we know firsthand how much more memorable staying in a rental home can make any vacation when compared to overbooked and noisy hotels.

When you book a Longboat Key rental for your trip, you’ll be able to rest easy knowing that your lodging is fully private and you’re guaranteed some much-needed peace and quiet. What’s more: our listings include homes of all sizes and locations, so finding the right rental home for you and your family is quick and easy.

Booking only takes a few minutes. After that, you’ll be one step closer to an incredible vacation in Longboat Key.

Best Restaurants Near Longboat Key Vacation Rentals


Love an ocean view when you’re dining? In Longboat Key, the closeness of the Gulf of Mexico and Sarasota Bay on either side means that nearly every restaurant in town has a view of the water.

Perhaps you’re looking for an upscale romantic establishment for date night or a casual spot for a quick lunch or dinner with family. No matter what sort of cuisine you desire, Longboat Key’s many eateries are sure to satisfy.

If you’re on a romantic getaway to Longboat Key with your significant other, you should consider making reservations at Euphemia Haye Restaurant. You’re guaranteed to have a memorable date night at this fine dining establishment.

Housed in one of the Key’s historic beachside cottages, the menu features a varied list of global dishes and plenty of fine wines. And once you’ve finished your dinner, you can head upstairs to The Haye Loft to enjoy a nightcap and a decadent dessert crafted by the incredible in-house chefs.

It wouldn’t be a proper trip to the Florida coast without some authentic and delicious seafood. The Lazy Lobster is the perfect spot to get just that, and it is only a few steps away from the shores of Sarasota Bay.

Each dish at The Lazy Lobster is crafted with only the freshest seafood and other locally sourced ingredients. Add in a varied list of unique cocktails and craft beers and you’ve got yourself a lively and delicious lunch or dinner.

If you’re ever in need of some coffee to fuel your long day of outdoor exploration, Turtle Coffee Bar is a local favorite for coffee and tea drinks of all kinds. Only adding to the magic is the fact that you can walk straight from the establishment to the beach in minutes by crossing Gulf of Mexico Drive.

Traveling to Longboat Key


If you’re flying into Florida to visit Longboat Key, the most convenient airport to use is Sarasota Bradenton International Airport. From there, it is recommended that you rent a car rather than use public transit so that you can visit the many destinations available and take your time along your route. A rental car also allows you to travel up and down Longboat Key with ease.

The drive from Sarasota Bradenton International Airport to Longboat Key is roughly 14 miles, which usually takes fewer than 30 minutes to complete. If you’re traveling into town from elsewhere in Florida, you’ll likely use routes like U.S. Highway 301 (north to south) and State Roads 72 or 70 (east to west) to reach Longboat Key.

Longboat Key Activities for Every Lifestyle


Though Longboat Key has a sleepy vibe perfect for slow-paced living and plenty of relaxation, there is no shortage of activities to explore. Whether you’re looking for an adventure or some calming pastimes to enjoy on your vacation, Longboat Key has it all.

For some fun in the sun, Bayfront Park is a popular destination. This public park is located right on the shore of Sarasota Bay, providing stunning ocean views as well as direct beach access.

Some other amenities that visitors can use at Bayfront Park include plenty of sports courts and open fields, a large play structure for kids, and picnic tables perfect for a casual lunch by the water.

Just south of Longboat Key on Lido Shores is the Mote Marine Laboratory & Aquarium. Here, visitors can learn all about the local marine life surrounding Longboat Key and beyond and gain a new appreciation for native wildlife. There are also plenty of hands-on exhibits and activities for kids and visitors of all ages to enjoy.

When you visit Longboat Key, you can explore many different beaches, all of which feature glistening white sand and warm turquoise waters. However, Little Beach is one of the town’s most popular lookouts and beaches. Protected by pieces of land, the waters at Little Beach are very calm and inviting for visitors of all ages.

Your perfect vacation in Longboat Key is waiting for you. Get started by perusing all of our rental homes on FloridaRentals today.


FAQ

How many vacation rentals are there in/around Longboat Key?

There are 58 Longboat Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Longboat Key?

There are vacation rentals available in Longboat Key for as low as $100 per night with an average price per night of $283.

Can I find a vacation rental in Longboat Key?

Yes, you can find vacation rentals in Longboat Key close to Coquina Beach, Durante Community Park, and Longboat Key. Don't forget to stop in to Quick Point Nature Reserve or Bayfront Park.

Do any vacation rentals in Longboat Key have a pool?

Yes, there are 10 vacation rentals with a pool in Longboat Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Longboat Key vacation rentals on the ocean?

There are 17 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!