Cheap Vacation Rentals in Longboat Key

(17 rentals)
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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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$100

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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.Available 2024 December. 2025 January through MayTropical paradise awaits you on Longboat Key. The folks at Twin Shores call this The Green House. A classic ...

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Property Type

Longboat Key Mobile Home

"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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1 BR | 1 BA | Sleeps 4 | Quick View

4

$120

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is ...

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Property Type

Longboat Key Condo

"Excellent Stay"

We had such a great time in this condo. It was convenient to pool and beach. Also some great restaurants close by. We enjoyed the manatees from the pool. We look forward to returning. What a great ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 150 yards to Gulf Of Mexico

$143

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Available now! Extra low rate for October and November. ! 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 ...

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Property Type

Longboat Key Apartment

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2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 0.3 miles to Gulf Of Mexico

$157

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly

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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2 BR | 2 BA | Sleeps 4 | Quick View

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

$158

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 500 yards to Whitney Beach

$174

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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

"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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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 500 feet to Private access

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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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2 BR | 1 BA | Sleeps 5 | Quick View

2

Distance to beach: 500 yards to Gulf of Mexico

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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

"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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$184

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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

"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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2 BR | 1.5 BA | Sleeps 4 | Quick View

1

$199

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • 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

"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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$200

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Rentals by owner

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

"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 Vacation Rentals