Longboat Key Vacation Rentals

(80 rentals)
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Longboat Key Apartment
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom

$342

avg/night

$342
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 Apartment
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
2 reviews

$318

avg/night

$318
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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$288

avg/night

$288
avg per night
View Details

Key Amenities

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

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
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$366

avg/night

$366
avg per night
View Details

Key Amenities

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

About this property

Experience Coastal Elegance at Beachplace PenthouseWelcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking ...

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Property Type

Longboat Key Condo

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Longboat Key Condo
3 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 3 bedrooms, 3 bathrooms

$323

avg/night

$323
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity that comes along seldom. This impressive home is your rental opportunity to live your best life and indulge in the finer things. As you step inside, prepare to be awestruck by the stunning ...

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

$274

avg/night

$274
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 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

Escape. Brand newly remodeled, featuring a fully equipped kitchen, blending modern comforts of an air fryer/convection combo with cozy charm. The loft-style layout includes a comfortable bed, ensuring restful nights in a peaceful setting.The cottage is bathed in natural light, thanks to large, well-placed ...

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

$188

avg/night

$188
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
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$325

avg/night

$325
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$292

avg/night

$292
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 Cottage
1 BR | 1 BA | Sleeps 1 | Quick View
Sleeps 1, 1 bedroom, 1 bathroom
1 review

$192

avg/night

$192
avg per night
View Details

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. A historical fisherman's village. House features high vaulted ceilings, a modern kitchen with SS appliances. Includes convection/air fryer/stove combo, & cutting-edge conveniences including high-speed ...

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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 Apartment
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
1 review

$342

avg/night

$342
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 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
  • Beachfront
  • Pool
  • WiFi

About this property

Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very rare find.Building Balcony work is occuring Jan and Feb 2025 Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Oceanfront ...

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Property Type

Longboat Key Condo

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

$336

avg/night

$336
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 ...

View all property information

Property Type

Longboat Key Condo

Show less

Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
last minute deal
LAST MINUTE DEAL 3/8 - 4/1: The Month of April price has been reduced. Please book this premier property today and come stay at

$266

avg/night

$266
avg per night
Offer for: Mar 8 - Apr 1:
The Month of April price has been reduced. Please book this premier property today and come stay at

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows ...

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Property Type

Longboat Key Condo

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

$259

avg/night

$259
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Updated top-floor 2 Bedroom + Den with a pullout sleeper with stunning water views from nearly every room. Enjoy the private beach just steps away, featuring 750’ of Gulf frontage and renowned sugary white sand. The open concept layout is perfect for coastal vacationing, complemented by two spacious ...

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$1022

avg/night

$1,022
avg per night
View Details

Key Amenities

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

About this property

Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool ...

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Property Type

Longboat Key Condo

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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
  • WiFi

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
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$515

avg/night

$515
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 Villa
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
1 review

$584

avg/night

$584
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 Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 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 3 bedroom, 2 bath condo. Open kitchen, spacious living room and an integrated dining room. Office den, ideal for working or relaxing. Master bedroom features a private balcony to enjoy the ocean and spectacular sunsets. Laundry room with full size washer and dryer. Two oceanfront balconies ...

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Property Type

Longboat Key Condo

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

Distance to beach: 150 yards to Gulf Of Mexico

$138

avg/night

$138
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 minutes to the 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 ...

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Property Type

Longboat Key Villa

Featured review

"Do overlook this little gem."

First and foremost, the owner is great to work with.I leased this 1 bedroom back in July of 2024. Not anticipating 2 very big storms. The owner Nancy kept me up to date on the progress of renovations ...

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

$332

avg/night

$332
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 Condo
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
1 review

$327

avg/night

$327
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 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

$160

avg/night

$160
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

$334

avg/night

$334
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 Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 500 feet to Private access

$155

avg/night

$155
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 Condo
1 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1 bathroom
11 reviews
last minute deal
LAST MINUTE DEAL 3/7 - 3/28: Stunning Gulf Views & Breathtaking Sunsets Just Steps to White Sand Beach! 2026 March available.

$264

avg/night

$264
avg per night
Offer for: Mar 7 - Mar 28:
Stunning Gulf Views & Breathtaking Sunsets Just Steps to White Sand Beach! 2026 March available.

View Details

Key Amenities

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

About this property

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 BE SYNCRONIZED. PLEASE SEND INQUIRY.Also I have garden view one-bedroom ...

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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 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!

$346

avg/night

$346
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
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 House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • 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 ...

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

$250

avg/night

$250
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 Studio
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$405

avg/night

$405
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck and onto the beach. Stay in this 2 bedroom (2 king beds), 2 bath condo . It is on the Gulf Side. Right on the Beach with amazing views. Condo is beautiful and in excellent condition

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Property Type

Longboat Key Studio

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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

$189

avg/night

$189
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 living area, kitchen and half bathroom are downstaris. Upstairs is the master bedroom with king bed and guest bedroom with 2 twins. The crib in the pictures has been removed and replaced with a desk & chair. ...

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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
3 BR | 2.5 BA | Sleeps 5 | Quick View
Sleeps 5, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

This fabulous, 2000-square-foot, fourth story, corner, direct beachfront, condominium features spectacular views of the gulf and bay. Hear the waves from the master suite and enjoy a dinner on the screened lanai while viewing one of Longboat's incredible sunsets. Sip a morning coffee on the back ...

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Property Type

Longboat Key Condo

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Longboat Key House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to Longboat

$809

avg/night

$809
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Imagine waking up to dolphins playing just beyond your window. This exquisitely renovated Longboat Key luxury waterfront home offers breathtaking "Big Bayfront" views and unparalleled access to the Gulf of Mexico. Boater's Dream: • Direct access to the Gulf for fishing or cruising • Private ...

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Property Type

Longboat Key House

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Longboat Key Condo
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 3 bathrooms

$341

avg/night

$341
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico. ...

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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

$356

avg/night

$356
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Sought after beachfront unit on the 5th floor of building 9 and an end unit. 2 bedroom, 2 bath unit with stunning views and very well appointing furnishings.Beachplace is one of Longboat Key's premier vacation rental locations on the island!Amazing Gulf Views and private parking.This ...

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Property Type

Longboat Key Condo

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

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

***CANAL VIEW HOME/WALK TO THE BEACH/NEWLY FURNISHED***Dreamed of living on an island? Look no further! Nice and quiet residential street in beautiful Longboat Key. This 2 bedroom, 1.5 bathroom sits on a water canal. Newly furnished with a farmhouse coastal decor offering two bedrooms on the second ...

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Property Type

Longboat Key Condo

Featured review

"Six Weeks In Paradise"

We spent the holidays and January in this wonderful and well-appointed condo on LBK. Our daughter from St. Pete joined us for Christmas and a few other weekends. We couldn’t have been more comfortable. ...

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Longboat Key Condo
1 BR | 2 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 2 bathrooms

$176

avg/night

$176
avg per night
View Details

Key Amenities

  • Hot tub
  • Pool
  • WiFi

About this property

This home located in the sought after Seaplace community has a very personal feel to it and has a balcony with a side view that highlights the Gulf of Mexico. This unit is perfect for a person or couple that wants to enjoy the beach and pool and stay in a friendly community. Master bedroom is spacious ...

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Property Type

Longboat Key Condo

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

$216

avg/night

$216
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 Condo
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

$183

avg/night

$183
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 Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$291

avg/night

$291
avg per night
View Details

Key Amenities

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

About this property

NO DAMAGE TO UNIT . WEEKLY & MONTHLY RENTAL ONLY. Seasonal rates apply. Harbour Villa Club is Longboat Key's best kept secret! Private location, bright & clean condo with spectacular views of the bay. Manatee County Sales of 6% is requested after your reservation. A guest registration ...

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Property Type

Longboat Key Apartment

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

$268

avg/night

$268
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades.The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs ...

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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

$255

avg/night

$255
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful beachview 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 system ...

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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

$356

avg/night

$356
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 House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 500 yards to Whitney Beach

$164

avg/night

$164
avg per night
View Details

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 on the northernmost end, is a lovely cottage steps from Sarasota Bay and 2 1/2 blocks from Gulf of Mexico with its own relaxing courtyard surrounded by beautiful lush ...

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Property Type

Longboat Key House

Featured review

"Location"

What a location! Walk to beach and local restaurants. Beautiful little cottage! Plan to return in 2024. Love that it pet friendly.

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

$299

avg/night

$299
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and ...

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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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Show less

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

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful unit on the 5th floor with lake/pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit.The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access ...

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Property Type

Longboat Key Condo

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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 80 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 $95 per night with an average price per night of $274.

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 13 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 20 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!