Luxury Vacation Rentals in Longboat Key

(37 rentals)
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2 BR | 2 BA | Sleeps 4 | Quick View

$606

avg/night

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Key Amenities

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

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
  • 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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2 BR | 2 BA | Sleeps 8 | Quick View

$563

avg/night

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Key Amenities

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

About this property

Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacations, the house was completely redecorated and stocked to offer all the comforts of home to our guests. A cool, beachy palette welcomes you to sit back and relax.Make plans now to ...

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Property Type

Longboat Key Villa

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3 BR | 3 BA | Sleeps 8 | Quick View

$523

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
  • Pet friendly
  • 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
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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
  • 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 ...

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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
  • Kitchen
  • Pool
  • Rentals by owner

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

$375

avg/night

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Key Amenities

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

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Apartment

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

**New Vacation Rental!** Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico with it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social ...

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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 6 | Quick View

$369

avg/night

View Details

Key Amenities

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

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Apartment

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Key Amenities

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

About this property

Gulf side paradise with hundreds feet of beautiful beach. This one bedroom condo on the fourth floor with a private balcony is the place to enjoy the sound of the rolling waves and some of the most spectacular sunsets on Longboat Key. Take the elevator and you’re just steps away from the heated ...

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Property Type

Longboat Key Condo

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$363

avg/night

View Details

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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Key Amenities

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

About this property

We have one more Mexican Gulf View unit 403 and garden one-bedroom #64 and Studio #63 units in this resort. Units 64 and 63 can be rented as 2-bedroom apartments.Welcome to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. See my site for more info: LongboatKeyParadise The unit ...

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Property Type

Longboat Key Apartment

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1 BR | 1 BA | Sleeps 6 | Quick View

$346

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifacts, 40 year old flooring, one SIZE fits all, etc.). We call it ...

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Property Type

Longboat Key Apartment

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3 BR | 2.5 BA | Sleeps 7 | Quick View

5

Distance to beach: 3 miles to Siesta Key Beach

$346

avg/night

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Key Amenities

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

About this property

SEASON RENTER CANCELLED. Owner looking for 3 month long rental (Jan, Feb, Mar 2024) Sprawling fully fenced& private ranch pool house ( 3 bed, 2.5 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 ...

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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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2 BR | 2 BA | Sleeps 5 | Quick View

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

$345

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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1 BR | 1 BA | Sleeps 6 | Quick View

$335

avg/night

View Details

Key Amenities

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

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical ...

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Property Type

Longboat Key Apartment

Show less

$309

avg/night

View Details

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 ...

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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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1 BR | 1 BA | Sleeps 6 | Quick View

7
last minute deal
LAST MINUTE DEAL 11/27 - 12/11: Beachfront with GULF AND SUNSET VIEWS! Dec 31-Jan 2 New Year available! Just 50 steps to the beach.

$308

avg/night

View Details

Key Amenities

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

About this property

GULF FRONT - ON THE SAND. SPECTACULAR GULF VIEWS AND SUNSET VISTAS.Also there are garden one-bedroom #64 and Studio #63 units in this resort. Pictures are at the end of photo gallery for they main listing. Units 64 and 63 can be rented as 2-bedroom apartments. Both with full kitchen and full bathroom.RATES ...

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Property Type

Longboat Key Condo

"Can’t Wait To Go Back!"

First impression is the spectacular wall-to-wall, floor-to-ceiling oceanfront view! It’s breathtaking. We enjoyed coffee each morning on the balcony soaking in the perfection of it all! After three days ...

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

$275

avg/night

View Details

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
  • 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 recently renovated, nicely furnished, and well stocked - designed for those who love to cook. This 2 bedroom, 2 bath first floor unit with fantastic bayou views its located ...

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Property Type

Longboat Key Apartment

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1 BR | 1 BA | Sleeps 4 | Quick View

1

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

$274

avg/night

View Details

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

"Fabulous location; wonderful, clean condo. Everything needed was provided. Wonderful staff from check in to maintenance."

Location was wonderful. Midway between Anna Maria Island and the pier to Sarasota and a more city vibe. Restaurants on Longboat were terrific (make reservations) Lazy Lobster; Shore;Salty Dog; Dry Dock; ...

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Key Amenities

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

About this property

2 bedroom/ 2 bath This newly renovated condo is the closest unit to the beach. It is located on the 2nd floor with elevator access. It has amazing ocean views from the living area, master bedroom, and covered patio. We often see dolphins from the patio. The master bedroom is located upstairs in the ...

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Property Type

Longboat Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 200 yards to Private Deeded Beach Access

$266

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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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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$248

avg/night

View Details

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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$245

avg/night

View Details

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

$241

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
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

PRIME LOCATION!!! 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 ...

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Property Type

Longboat Key Condo

"Peaceful Stay in Paradise"

Tara was an excellent host, quickly answering every question and concern. We had everything we needed for a comfortable and peaceful stay. The fully-stocked kitchen made cooking easy at home, and we spent ...

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3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.2 miles to Whitney Beach

$211

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 ...

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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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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 50 yards to Our own private beach!

$206

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Relax in this privately owned, Old Florida Charm, “coastal themed” ground floor condo located on the Southern Gulf side of Florida. The condo offers views of the Sarasota Bay, a community heated pool, hot tub, boat dock, and a three minute walk to the private beach with turquoise waters on ...

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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

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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Longboat Key Vacation Rentals