Longboat Key Vacation Rentals

(52 rentals)
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Key Amenities

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

About this property

Welcome to the Pet Friendly Tropical Paradise House. Once you drop your suitcases, you’re a short 3-minute walk to sugar soft white sand on your own private beach.  Bring your favorite bottle of wine, while you admire the beautiful orange warm Florida sunset from your own gazebo (complete with ...

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Property Type

Longboat Key House

"Perfect Quiet Location"

Loved how close the beach was to the house, very quiet and relaxing neighborhood. House very spacious.

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2 BR | 2 BA | Sleeps 4 | Quick View

$231

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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1 BR | 1 BA | Sleeps 4 | Quick View

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

$242

avg/night

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Key Amenities

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

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

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 150 yards to Gulf Of Mexico

$124

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 beachAdorable 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 (see photo) and 3 minute walk to the neighboring 32 acre Durante Park FULL of fabulous ...

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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

About this property

Enjoy the beauty of this updated condo located just steps to the beach! The new tile flooring, open kitchen and the upscale furnishings will make your vacation that much more enjoyable. Beachplace offers you a luxury resort-style living that features a large pool with a lap lane, hot tub, kiddie pool, ...

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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 6 | Quick View

6
LAST MINUTE DEAL 1/24 - 2/7: Beachfront with A VIEW! Booking for Season 2024 started.Balcony Gulf View. Have two more, same place

$265

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

GULF FRONT - ON THE SAND. SPECTACULAR GULF VIEWS AND SUNSET VISTAS.RATES ARE SUBJECT TO CHANGE WITHOUT UPDATING ON THIS PLATFORM. CAN BE LOWER OR HIGHER. PLEASE REQUEST.Recently upgraded with all new furniture, 55'' smart 4-K TV, 24" smart TV in the bedroom, kitchen dinnerware, lights ...

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Property Type

Longboat Key Condo

"Amazing"

Stayed 5 days. The place is fantastic, the view spectacular. I highly recommend this location and unit. The beach is incredibly close and very peaceful. If you want a busier beach Lido and Siesta are a ...

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DEAL

1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 50 feet to Beach Access Directly Across the Street

$141

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Come enjoy sunsets of the Gulf of Mexico's turquoise waters. Located directly across the street from one of the nicest secluded beach accesses in the area. This second floor unit is just steps across from a beautiful beach access on Longboat Key, Florida. Turnkey furnished 1 bedroom, 1 bathroom vacation ...

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Property Type

Longboat Key Condo

"Beautiful Unit and Amazing Location"

This is a beautiful unit, and such a peaceful, perfect location. Short walk to the beach and short walk to grocery store . Very private! Denise is an amazing host and very accommodating! I would highly ...

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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
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Comfortable home with the charm of old Florida, costal décor, and eclectic antiques. Canal side with water views and only steps from a sharable day dock on the bay. Master Bedroom and office are located upstairs with a remarkable view of the Sarasota Bay. Minutes from gorgeous beaches. Beautiful ...

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Property Type

Longboat Key House

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4 BR | 2 BA | Sleeps 9 | Quick View

$319

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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$294

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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$218

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

"Best decision I ever made!"

My first trip to the Sarasota area but certainly not my last! I stayed in this condo for approximately 2 months and it was the best two months I've had in a very long time! The condo is clean, attractively ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$542

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

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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Key Amenities

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

About this property

Sprawling ranch pool house ( 3 bed, 2 bath, one car garage) in one of the best neighborhoods in Sarasota (please note, this house is in Granada Sarasota, NOT Longboat Key), 5 minutes from the gorgeous beaches of Siesta Key Beach and 7 minutes from downtown Sarasota as well as 5 minutes from the best ...

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Property Type

Longboat Key House

"Great tropical retreat"

Great location, beautiful neighborhood. The house is spacious, comfortable, kitchen has everything you need. The outdoor patio with a pergola and fan, surrounded and covered by a magnificent tropical jungle ...

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$350

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Surrounded by tropical landscaping & fruit trees on a corner lot, this cozy 3 bed/2 bath home features an open floor plan w/new kitchen & remodeled baths. Those who enjoy a quiet retreat will enjoy the pond with lilly pads & fire pit. LBK's historic fisherman's village combines rich history ...

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Property Type

Longboat Key House

"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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Key Amenities

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

About this property

NEW LISTING! Newly remodeled charming 2 bed/ 1 bath condo 5 min walk from beach entrance and shops. Nestled in a quiet area, our place is perfect to relax and enjoy beach style leaving.Fully equipped kitchen with upgraded stainless steel appliances (dishwasher included) beautiful new quartz counter ...

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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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Enjoy being located in heart of LongBeach, a historical fishing village on Longboat. This is a compound that may be leased separately as a 3 bed/2 bath main house + two 1bed/1 bath guest cottages, all remodeled/newly furnished + smart TV's. High vaulted ceilings in cottages. Brand new & updated ...

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Property Type

Longboat Key Estate

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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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$243

avg/night

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Key Amenities

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

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

"Loved 'Our' Home for a Month!"

Sometimes we hesitate to give a great review because we're selfish. We don't want to share a great find! First off, the owners could not of been nicer. Nice goes a long way with us. Secondly, clean is at ...

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$158

avg/night

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Key Amenities

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

About this property

Newly decorated and all new furnishings, beautiful unit, with stunning, really stunning views from every room. Wake up and watch the pelicans soar by and fish breaking water. Private, beautiful sandy beach with bathrooms, showers and tables. Kayak launch, clubhouse, two gorgeous pools, one right on the ...

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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

5.0 rating on other travel sites

$187

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Sit back and relax and watch the Manatees in the canal outside your window for your 1st floor 1 bedroom condo at Whitney Beach on the north end of Longboat Key. The one bedroom condo is over sized and provides all you need for the perfect vacation.*** This property requires an rental application to ...

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Property Type

Longboat Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

5.0 rating on other travel sites

$458

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 private 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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3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.2 miles to Whitney Beach

$208

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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Key Amenities

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

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 a nicely furnished, well stocked, 2 bedroom, 2 bath first floor unit with fantastic bayou views in the sought after Whitney Beach Community. The Whitney Beach community has ...

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Property Type

Longboat Key Apartment

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3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 200 yards to Private Deeded Beach Access

$244

avg/night

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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 family vacation"

We had a wonderful vacation! The house was super clean when we arrived. There were bikes to ride, beach chairs & umbrellas and beach towels. All the comforts of home were provided. The kids loved fishing ...

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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
  • 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

"Snowbird perfect"

This was a perfectly cozy and comfortable January retreat. The unit delivered on everything promised and the condo complex amenities could be among the best that LB Key has to offer. Truly great access ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Situated on Longboat Key, this secured and gated 1st floor 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, dishwasher, ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

**Welcome to our beachfront Longboat Key condo!If you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos ...

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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: 5 feet to Just outside your door & window

$225

avg/night

View Details

Key Amenities

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

About this property

Renter cancellation for 2023 due to a family health issue. Had been rented for 2023 since January and just opened up this week.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. ...

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Property Type

Longboat Key Condo

"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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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. Updated photography ...

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Property Type

Longboat Key Condo

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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
  • 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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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

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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 and ...

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Property Type

Longboat Key Condo

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Key Amenities

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

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 lanai ...

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Property Type

Longboat Key Condo

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Key Amenities

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

About this property

This gorgeous 2 Bedroom / 2 Bath spacious, bright condo located in the beautifully maintained association of Whitney Beach on Longboat Key. You can have it all- Gulf and Bay access! Natural light floods the open floor plan, which features a breakfast bar, dining area with bar area, living room and lanai ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to Bayport Beach and Tennis Club!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 inviting atmosphere. Enjoy sunrises over the bay, sunsets on the ...

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Property Type

Longboat Key Condo

"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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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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

SEASONAL/VACATION RENTAL! New Remodel completed August 2022! AVAILABLE September through spring 2023 Season. Take your next vacation in paradise and be the first to stay in this gorgeously renovated, modern condo! Club Longboat Luxury Condo community is a beach and tennis club with all facilities most ...

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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$236

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

The unit is a 1 bedroom 5th floor condo directly on the beach in beautiful Longboat Key. There is beachfront pool as well as a gas grill for barbecuing at the beach. The unit has a partial water view of Sarasota Bay. Walking distance to restaurants and shops including a Publix and CVS.

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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.

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Property Type

Longboat Key Condo

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Key Amenities

  • Kid friendly
  • Kitchen
  • Pool

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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4 BR | 4.5 BA | Sleeps 10 | Quick View

1

$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Custom designed waterfront home located on a deep wide canal in Sleepy Lagoon on north end of Longboat Key with access to the Intracoastal Waterway. This beautiful home has four bedrooms, each with their own private bathroom, plus a den and a half bath which has access to the large Heated swimming pool. ...

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Property Type

Longboat Key House

"Amazing stay"

This was the most amazing stay vacation I ever had my family was very comfortable all needed was on site all was very clean and easy to find. Shop's and beaches close by. I would highly recommend using ...

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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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Key Amenities

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

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

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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 500 yards to Whitney Beach

$172

avg/night

View Details

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 tropical landscaping. ...

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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

$270

avg/night

View Details

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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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°

FAQ

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

There are 52 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 $124 per night with an average price per night of $257.

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 12 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 9 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!