Luxury Vacation Rentals in Longboat Key

(36 rentals)
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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
  • 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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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 | 4.5 BA | Sleeps 10 | Quick View

1

$500

avg/night

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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
  • 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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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
  • 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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2 BR | 2 BA | Sleeps 4 | Quick View

$441

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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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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Key Amenities

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

About this property

Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. The sunsets are breathtaking. You will love the beach views and fast Wi-Fi. This is a luxury rental. Condo has a single unit washer/dryer in one. There is a Islands West is the ideal ...

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Property Type

Longboat Key Condo

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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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3 BR | 2 BA | Sleeps 6 | Quick View

5.0 rating on other travel sites

$335

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
  • 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
  • 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

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 condo ...

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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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1 BR | 1 BA | Sleeps 6 | Quick View

6
LAST MINUTE DEAL 3/26 - 4/9: Direct Gulf Front! Fantastic views! Some June, July, Aug still available. 2-3 rare night min. stay.

$284

avg/night

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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

$267

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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$265

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
  • 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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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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$242

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

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

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

$233

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

2

Distance to beach: 200 yards to Private Deeded Beach Access

$223

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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2 BR | 1 BA | Sleeps 5 | Quick View

5

$214

avg/night

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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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1 BR | 1 BA | Sleeps 4 | Quick View

$213

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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2 BR | 2 BA | Sleeps 4 | Quick View

$206

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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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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3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.2 miles to Whitney Beach

$204

avg/night

View Details

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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$201

avg/night

View Details

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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2 BR | 2 BA | Sleeps 5 | Quick View

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

$200

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