Cheap Vacation Rentals in Longboat Key

(15 rentals)
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Longboat Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

$94

avg/night

$94
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful, peaceful one bedroom / one bath condo on Longboat Key. Amazing view and breeze from the lanai. Private friendly gated community with great amenities. Four pools, tennis court, BBQ girls, shuffleboard, work out facilities, game room. Private beach access across the street with private bathrooms ...

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Property Type

Longboat Key Condo

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Longboat Key Mobile home
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$100

avg/night

$100
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Great beach house on Longboat Key. Over 55 community two person occupancy limit with allowances for guests, no pets, parking for one vehicle.Next availability. July, August, September 2025, January 2026Tropical paradise awaits you on Longboat Key. The folks at Twin Shores call this The Green ...

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Property Type

Longboat Key Mobile Home

Featured review

"Slice of Beach Paradise - Immaculate and beautifully restored 1950's trailer"

I rented this adorable beach tiny house for 2 years during the season. Dec 2022-Apr 2023 & Nov 2023-Apr 2024. I cannot say enough about the house, location, community and the landlord. 2 Bed, 2 BA (1 ...

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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

$121

avg/night

$121
avg per night
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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 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

$137

avg/night

$137
avg per night
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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 House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

$150

avg/night

$150
avg per night
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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
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 500 feet to Private access

$152

avg/night

$152
avg per night
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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 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

$155

avg/night

$155
avg per night
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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
1 BR | 2 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 2 bathrooms

$158

avg/night

$158
avg per night
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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 House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 500 yards to Whitney Beach

$162

avg/night

$162
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

"cozy cottage"

The cottage is in a great location on Longboat Key. It is small but having the outside patio was nice extra space to use. Quick walk and view of the bay, and not a long walk to the beach.

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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

$172

avg/night

$172
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 Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

$177

avg/night

$177
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
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

$178

avg/night

$178
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
1 review

$186

avg/night

$186
avg per night
View Details

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 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 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 Vacation Rentals