Longboat Key Vacation Rentals

(30 rentals)
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Longboat Key 29

4 BR | 4.5 BA | Sleeps 8 | Quick View

$525

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Luxury Rental Home on Longboat Key. Newly built 4 bedroom, 4.5 bath single family home with a private attached guest suite. This home has many luxury details including the gourmet kitchen which is equipped with a wet bar and all WOLF appliances, SUBZERO refrigerator and wine cooler, Spanish porcelain ...

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Property Type

Longboat Key House

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Travel, Relax, Live! Enjoy the Sea Air, Private Beach, St. Armands and more...

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 60 yards to Longboat

$142

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Newly REMODELED!!One Bedroom, One Bath, Sleeps 4, Patio with Ocean Views, Great Location to St Armonds.Stunning one bedroom one bath unit within just a short walk to Longboat Key Beach. Come enjoy beautiful Sunsets and put your toes in the sand! This unit is equipped with a full kitchen and ...

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Property Type

Longboat Key Condo

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Swept Away

5 BR | 5.5 BA | Sleeps 10 | Quick View

$2000

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool

About this property

This house is STUNNING! Located on a PRIVATE, gulf-side street with 8 other luxury mansions it also has it's own PRIVATE beach access. No worries about having to pack the car up and head to the local public beach fighting traffic and people... just slip on your flip-flops and walk on to the spectacular ...

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Property Type

Longboat Key House

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Beachplace 3 Bedroom/2 Bath Condo

$264

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • 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

"Wonder 3 bedroom in Beachplace"
Reviewed July 28, 2020

This 3 bedroom 2 bath condo unit has been totally updated with tasteful furniture and finishes. Being a corner unit, there are great views of gulf (side view), Sarasota Bay, Sarasota city and community ...

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Paradis Sur Mer

4 BR | 4 BA | Sleeps 8 | Quick View

$381

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Paradis Sur Mer: Divine 4th floor 4 BR / 4 BA condo with breathtaking ocean views. Welcome to Paradis Sur Mer! In need of an ocean view? We have you covered. This fourth floor 4-bedroom, 4-bath condo has views for days!As you enter the condo through your private elevator, you will find an open floor ...

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Property Type

Longboat Key Condo

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ADORABLE LOW COST PRIVATE 1BR VILLA- 1.5 blocks to BEACH- at GREAT prices!!

1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 150 yards to Gulf Of Mexico

$116

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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

"Cozy"
Reviewed December 22, 2019

The condo is in an amazing location, small but cozy It had everything you need Probably the cleanest and the most comfortable place we've been to and close to the ocean There's a path to Joan Durante Park ...

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Lovely 3 bedroom condo with bay to Gulf views

$117

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Stunning condo on beautiful Longboat Key available for monthly rentals. 3rd floor (top Floor) corner unit with 2 lanais with beach and bay views The condo is completed updated with a fully equipped, modern kitchen, open concept living area, dining and kitchen. Master bedroom has a king sized bed and ...

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Property Type

Longboat Key Condo

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Bay Breeze

2 BR | 2 BA | Sleeps 4 | Quick View

$160

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to Bay Breeze! This charming 2 bedroom 2 bathroom second floor condo in the prestigious Windward Bay community has views of the bay from every room! Windward Bay is a highly desirable community boasting many amenities including private deeded beach access just across the street, 1/2 mile of private ...

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Property Type

Longboat Key Condo

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Breathtaking New 4 Bedroom 3 Bath Pool Home on South Longboat Key!

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 2 miles to Lido Beach (Lido Key)

$375

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

THIS UNIT IS AVAILABLE A MINIMUM 30 DAYS MINIMUM DUE TO CODE - Please see COVID Cancellation Policy below - it is different from VRBO policy options.Limetree House. This fabulous newly constructed 4 bedroom 3 bath, saltwater pool home is located on the south end of Longboat Key. Spacious with an ...

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Property Type

Longboat Key House

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Steps to the Gulf of Mexico! Relax and Enjoy the Beach, Pool & Longboat Key!

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: May is a Beautiful Month in Longboat Key! Celebrate 20% Off May! Enjoy Being Outdoors Again!

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

$177

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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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Exotic Polynesian Tree House w26' pontoon boat

$1189

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

*Property is Accessible Boat Only* This is an exclusive " True Waterfront" pod-style home consisting of 6 bedrooms and one main living room/kitchen pod all interconnected with covered walkways with water views from all rooms. All amenities are right on property including your private beach. ...

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Property Type

Longboat Key House

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SARASOTA- Fantastic Florida Ranch Pool House in a Million Dollar Neighborhood

$170

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 house in nice location"
Reviewed March 15, 2021

We arrived late, as in after dark, I just want to get out of the car, on a Saturday night. Nikki had stopped by ahead of time and turned on lights and texted me pertinent info for arrival. The house was ...

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2BR/2Bath Luxury Condo

2 BR | 2 BA | Sleeps 4 | Quick View

1

$193

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

For those who do not know Beachplace, it is more of a resort than it is 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 and more. This beautiful 5th floor corner unit has amazing views of the Gulf ...

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Property Type

Longboat Key Condo

"Best decision I ever made!"
Reviewed August 19, 2020

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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A couple’s retreat. Condo Nestled in quiet area. Walk to beach & shops.

$182

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

NEW LISTING! Newly remodeled charming 2 bed/ 1 bath condo 5 min walk from beach and shops. Nestled in a quiet area, our place is perfect to relax or work remotely. We offer Super Fast 600MBPS internet!Fully equipped kitchen with upgraded stainless steel appliances (dishwasher included) beautiful ...

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Property Type

Longboat Key Villa

"Beach House Paradise!"
Reviewed January 4, 2021

This is truly a beach house paradise in LBK. The condo was spotless clean when we arrived, and Camila was a wonderful host. She made sure we had everything we needed for a restful week- comfortable beds, ...

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The Beach Nest

3 BR | 2 BA | Sleeps 6 | Quick View

$372

avg/night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

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 property located within walking distance to the longboat key beaches. This modern luxury property has all the amenities, including designer furniture, ...

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Property Type

Longboat Key House

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Cozy Beach Condo Pet-friendly, Longboat Key, Florida

1 BR | 1 BA | Sleeps 2 | Quick View

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

$120

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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 pet friendly second floor unit is just steps across from a beautiful beach access on Longboat Key, Florida. Turnkey furnished 1 bedroom, 1 ...

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Property Type

Longboat Key Condo

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180 Panoramic beach View and amazing Sunset.

1 BR | 1 BA | Sleeps 6 | Quick View

3
LAST MINUTE DEAL 4/18 - 5/1: Aug 8-28 available. Main picture with Gulf View from the balcony to enjoy with your morning coffee!

$225

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

GULF FRONT - ON THE SAND SPECTACULAR GULF VIEWS AND SUNSET VISTASUpgraded in 2019 with all new furniture, 55'' smart 4-K TV, 24" smart TV in the bedroom,kitchen dinnerware, lights and so on. All new 2 Queen beds in the bedroom and Full sleeper sofa bed in the living room.Watch dolphins ...

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Property Type

Longboat Key Condo

"Amazing"
Reviewed July 24, 2020

This apartment was perfect! This is definitely our new place for our getaways now! The views are to die for, we even got to see dolphins from our balcony. It was clean and beautifully decorated! We had ...

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DEAL
Vintage Florida Beach Cottage in historic Longbeach Village

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.2 miles to Whitney Beach

$143

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Perfect home away from home"
Reviewed July 14, 2019

My husband and I stayed here July 6-13 and absolutely fell in love with this place. The house was clean, spacious (pictures do not do justice) and very inviting. There were plenty of supplies and everything ...

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Beachplace in Longboat Key - resort style vacation

$250

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Enjoy the beauty of this remodeled condo. 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, fitness facility, tennis and ...

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Property Type

Longboat Key Condo

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Castillian Condo Beach Front Longboat Key, FL

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

BEACHSIDE VACATION RENTAL WITH FULL GULF VIEW. Spectacular Gulf views from this furnished 2 bedroom, 2 bath unit directly on the beach. Unit has two king size beds (Temper-Pedic adjustable bed in primary bedroom) and fully equipped kitchen with in unit washer/dryer. Beach views from living room and primary ...

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Property Type

Longboat Key Condo

"UNREAL!"
Reviewed February 16, 2021

Nothing but amazing things to say about this condo and Denise! The view directly looking out at the beach is unbeatable. 3rd floor is excellent for view and easy to go up and down from pool/beach. The ...

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Beachcomber Longboat Key

1 BR | 1 BA | Sleeps 4 | Quick View

$190

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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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Longboat Key Harbour

1 BR | 1 BA | Sleeps 4 | Quick View

3

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed February 3, 2021

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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Charming Beach House with Private Pool & Beach Access on Longboat Key

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 200 yards to Private Deeded Beach Access

$232

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

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 golden sunsets. Well maintained house with ...

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Property Type

Longboat Key House

"Great family vacation"
Reviewed January 7, 2021

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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Stunning Longboat Key Sarasota Bay water views

$154

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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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Island Village Cottage Compound Steps to the Sand

$777

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Enjoy a family compound located in heart of LongBeach, a historical fishing village on Longboat. Property offers 3 bed/2 bath main house + two 1bed/1 bath guest cottages, all remodeled/newly furnished + smart TV's. High vaulted ceilings in cottages. Decorated to match old-Florida feel of the keys w ...

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Property Type

Longboat Key Estate

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Majestic waterfront home on Longboat Key, FL

$583

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Majestic 4 bed 4 ½ bath 1 home from open water of Bay sits on a canal with 16,000 lb. boat lift/dock, pool/spa, large lanai and grill. Kitchen boats beautiful granite withViking stainless appliances. Has a formal living room with a fireplace, formal dining room and family room. The gym is loaded ...

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Property Type

Longboat Key House

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April Availability --- Historic "Old" Florida Cottage ~ Mable's Place

$160

avg/night

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Key Amenities

  • Air Conditioning

About this property

“Mable’s Place” is a historic beach cottage within walking distance of the Gulf of Mexico. This quaint 2 bedroom cottage has a quiet backyard surrounded by native Palm trees and equipped with a grill & Patio seating. This is a clean and comfortable 2 bedroom, 2 bath home that sleeps ...

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Property Type

Longboat Key House

"Piece of Paradise"
Reviewed December 8, 2020

This beach cottage is absolutely beautiful! Decorated with a mix of modern and vintage pieces, it is immaculately clean and efficient while remaining cozy and comfortable! Excellent location between the ...

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Tranquil Retreat, Heated Private Pool, Easy Walk to Beach, Bay

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to 100 Broadway Street, Longboat Key, FL

$127

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

You'll be enchanted by our lovely Key West style home in historic, laid back Longbeach Village at the north end of exclusive Longboat Key. Tastefully relaxed interiors are exquisitely complimented by a heated tropical pool area whose quiet, spa-like ambiance and sparkling waterfall will be yours to enjoy ...

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Property Type

Longboat Key House

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Quiet Island Paradise

3 BR | 3 BA | Sleeps 6 | Quick View

$395

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighbourhood. Take a leisurely 5 minute stroll to the pristine and serene beach, local park, kayaking and finest restaurants. Perfect for couples looking for privacy in splendid, tropical surroundings with resort ...

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Property Type

Longboat Key House

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Luxurious House on Canal* Beach Walkable* Coveted Southern End*From $246/night

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

The Pineapple Cottage is a special oasis of tranquility and comfort. Surrounded by the palm trees that symbolize Florida, it is a private home nestled on a canal that leads directly into Sarasota Bay. Our home is situated in the desirable neighborhood of Country Club Shores --- just a short ride from ...

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Property Type

Longboat Key House

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Longboat Key Vacation Rentals

Longboat Key Weather

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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°