Longboat Key Vacation Rentals with Private Pool

(13 rentals)
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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

New new new! More photos coming. Charmingly remodeled bungalow blocks from Whitney Beach & a block from bay. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! ...

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Property Type

Longboat Key House

"Beautiful accommodations"

After my first great experience at the landlord’s other property, I booked this one. Again, the landlord was fabulous and met all our needs. The furnishings were beautiful and very clean. The beds are ...

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4 BR | 2 BA | Sleeps 4 | Quick View

$429

avg/night

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Key Amenities

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

About this property

Enjoy this serene property and location...steps from the sandy white beach and the beautiful Gulf of Mexico waters on Longboat Key. This spacious home has been recently updated and will provide a peaceful and relaxing vacation. There are no resort fees, and there is plenty of private parking, and again ...

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Property Type

Longboat Key House

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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.1 miles to 3355 Gulf of Mexico Drive

$200

avg/night

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Key Amenities

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

About this property

Charming condo on Gulf of Mexico Drive, the beach access is across the street from our parking lot, literally steps away to the Gulf. Located in the "Dock on the Bay", we enjoy the benefits of a smaller association. The landscaping and property reflect what all of Florida once looked like. We ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

SCHILLER - 2 Bedrooms, 2.0 Baths (Sleeps 4)Minimum 1 month lease. Please see COVID 19 AND STANDARD CANCELLATION POLICY BELOW - it is different from VRBO policy options as are payment options. Arrivals prior to 90 days are to be paid in fullCharming, waterfront Longboat Key surprise! This 2 bedroom ...

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Property Type

Longboat Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.2 miles to Whitney Beach

$204

avg/night

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Key Amenities

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

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 stretch of ...

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Property Type

Longboat Key House

"Paradise"

Wonderful location in quiet neighbor. Walking distance beach and fishing pier. We enjoyed our stay!

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3 BR | 2 BA | Sleeps 6 | Quick View

5.0 rating on other travel sites

$340

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

What's better than your own private paradise? Come and enjoy 'Fine Living' at its best in this beautiful, recently remodeled, canal front 3 bedroom/2 bathroom home with heated pool located within walking distance to the Longboat Key beaches. This modern, luxury property has all the amenities, including ...

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Property Type

Longboat Key House

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Key Amenities

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

About this property

Welcome to Peacock Paradise, a tropical oasis nestled within the historic Longbeach Village at the north end of Longboat Key. Perfectly situated between gulf and bay, enjoy a quick walk to the beach, bay, boat launch, and several amazing restaurants like Shore, Mar Vista, Whitney’s, and more. Make ...

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Property Type

Longboat Key House

"Incredible Beach House Rental on Longboat Key"

My family rented this property from NYE till the week following of 2023 and it was truly an amazing experience from start to finish (it was my me, my husband and our toddler daughter + small dog). The host ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This home is located behind the coveted gates of the Longboat Key Club. This 4 bedroom home is only 150 yards away from the beach with access. The magnificent two-story-high volume ceilings in the formal living and dining areas offer natural light and vibrant green golf course views through glass sliders ...

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Property Type

Longboat Key House

"Great location within Longboat Key Club Resort"

1001 Longboat Club Road is the perfect location within the gates of the Longboat Club Resort. We have rented this house 6 years in a row. The house is large, the pool is huge and the beach is a block away. ...

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Key Amenities

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

About this property

*****The home is rented January, February and March of 2023***** Our home has everything needed for a wonderful Florida vacation! Located in Country Club Shores on the southern end of Longboat Key the beach is just a quick stroll away. This 3 bedroom 2 bath canal home with updated kitchen & baths, ...

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Property Type

Longboat Key House

"Exceptional"

This home was absolutely beautiful. The decorations, cleanliness and amenities were above par. In the 8 years I have been coming to Longboat Key , this home was by far the best. I definitely will rent ...

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3 BR | 3 BA | Sleeps 8 | Quick View

$489

avg/night

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Key Amenities

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

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

3 Bedroom 2 Baths and accommodates (6) (and a furry friend depending on breed) PLEASE SEE COVID 19 / STANDARD POLICIES BELOW - it is different from VRBO policy options as are payment options. Arrivals prior to 90 days are to be paid in full. Please note that the minimum lease period a month. due to City ...

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Property Type

Longboat Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the southern ...

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Property Type

Longboat Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 200 yards to Private Deeded Beach Access

$224

avg/night

View Details

Key Amenities

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

About this property

*** CONTACT OWNER FOR CURRENT AVAILABILITY ***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) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing ...

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Property Type

Longboat Key House

"Great canal home that is well stocked and as a bonus is pet friendly"

We thoroughly enjoyed or stay. It is in a great location on a quiet street with a very short stroll to the beach. The house is clean, comfortable, and well stocked with all the essential items you need ...

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Longboat Key Vacation Rentals