Longboat Key Florida Vacation Rentals, Hotels & Resorts

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Longboat Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Canal front cottage, walking distance to sandy Gulf

Longboat Key Private vacation home - 5.0 5.0 Star Review

Comforts of home with a fully equipped kitchen and washer/dryer. New queen and XL twin beds. Bedding and sheets supplied. Enjoy local restaurants, white sand beaches and fish the canal, bay or Gulf........read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Spacious 2Bdrm Longboat Key Condo

Longboat Key Condo - 5.0 5.0 Star Review

Paradise awaits in this beautiful 2 bedroom/2.5 bath condo in the heart of Longboat Key. Conveniently located near Sarasota, situated right on Gulf of Mexico Drive, you\'re a short walk to Longboat Key Beach or just a short drive to several other area beaches .There is also bay access on the rear of the property where you will find a small private.......read more

2 Bedroom(s)
Condo

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Luxurious Beachfront Villa with Private Pool

Longboat Key Condo - 4.92308 4.9 Star Review

This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secluded beach, heated community pool, private balconies, community hot tub and secure access. The unit is recently renovated and located across the street from a public park, a convenience store, two restaurants and a bicycle shop. .......read more

3 Bedroom(s)
Sleeps 8
Condo

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Silver Sands #245: 1 BR / 1 BA Resort on Longboat Key, Sleeps 4

Longboat Key Condo - 4.44444 4.4 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

Studio
Sleeps 4
Condo

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Million Dollar View!

Longboat Key Condo

Enjoy what I call my ‘Million Dollar View’ of the turquoise Gulf of Mexico ocean and sugar white sand. This second story condo is located in the Longbeach complex on the north end of Longboat Key and is located in one of the buildings closest to the beach. Live serenely in this pristine location knowing that the party and fun of Anna Maria Island a.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Beach Castle #1: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo - 4.78571 4.8 Star Review

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature.



The grounds here .......read more

2 Bedroom(s)
Sleeps 6
Condo

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Beach Castle #23: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo - 4.76923 4.8 Star Review

Relax in this privately owned and completely updated “coastal themed” ground floor condo that sleeps 4 with bay views from the privacy of your screened lanai, the living room and bedroom! The one-bedroom, one-bathroom condo includes new updates throughout: HVAC system with UV filtration system, full-size kitchen with granite counters, fully equipp.......read more

Studio
Sleeps 4
Condo

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Gulf Front, luxury condominium in beautiful Long Boat Key, FL

Longboat Key Condo - 5.0 5.0 Star Review

Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upscale, direct waterfront, luxury condo. This 3rd floor unit has incredible unobstructed views of the gulf---- direct views from living area and both bedrooms. Our condo boasts a full length, gulf front screened lanai with sliding door.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Your Arrival To Paradise Awaits Bay to Beach Condo

Longboat Key Condo

A unique hidden gem. Our condo is an upscale, private and beautiful retreat. This 2 bed 2 bath condo has been totally updated. We have installed new stone flooring, fresh paint and new furnishings as well as all new stainless appliances and kitchen hardware and new full size washer and dryer. Our condo is kept super clean, and we promise you .......read more

2 Bedroom(s)
Sleeps 4
Condo

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PARADISE FOUND* PEACEFUL & ELEGANT UPDATED *CANAL HOME *WALK TO BEACH* NEW BIKES

Longboat Key Private vacation home - 5.0 5.0 Star Review

*****ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT****PLEASE PROVIDE DETAILED DESCRIPTION OF TRAVELERS WHEN REQUESTING A BOOKING ****CONTACT US FOR CANCELLATION TERMS

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 cana.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Luxury Condo located on Beachfront Property

Longboat Key Condo

We just purchased this condo and it will be ready for Rental in December 2022 . The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise........read more

2 Bedroom(s)
Sleeps 6
Condo

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Key Lime Cottage: Stunning condo with a Bay View from the front door!

Longboat Key Condo

Welcome to Key Lime Cottage! This gorgeous 1-bedroom, 1-bathroom condo offers the perfect location. Located between the bay and the beach you are bound to have endless adventures.

The community of Beach Club Harbor offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get .......read more

Studio
Sleeps 4
Condo

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Updated Beachfront Studio w/ Sparkling Pool, Breezy Patio & Modern Kitchen

Longboat Key Private vacation home - 4.45455 4.5 Star Review

The Beach On Longboat Key Resort #105

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Beach bliss awaits at this updated coastal studio located in the heart of Longboat Key. Enjoy the Gulf breeze on your shaded patio, or stroll to the heated poo.......read more


Beautiful Longboat Key RESORT 2 bed/2 bath, Sleeps 6,Granite/Stainless Kitchen

Longboat Key Hotel resort

Longboat Bay Club provides vacation accommodations that include recreation and pampered relaxation. Take advantage of the peace and privacy of a smaller property with the amenities of a larger resort. You will have plenty of room for relaxing in our 1600+ sq. ft. condominiums, each with a washer/dryer inside for your convenience. Our units also boa.......read more

2 Bedroom(s)
Sleeps 6
Hotel resort

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Stunning Beach Front Condo on the most private and select beach in Longboat Key.

Longboat Key Condo

Are you looking for a quiet and select non touristy location right on what happens to be one of the most spectacular and unpopulated secluded beaches in Longboat Key? This is why we brought this beautiful bright and spacious condo with balcony for its staggering views and sunsets plus totally renovated to a gourmet kitchen and bathroom with waterfa.......read more

Studio
Sleeps 2
Condo

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Silver Sands #239: 2 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo - 4.75 4.8 Star Review

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch.......read more

2 Bedroom(s)
Sleeps 6
Condo

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1000 Ft of private Gulf of Mexico Beach

Longboat Key Condo

1000 Feet of private beach in this one of a kind north end Whitney Beach 1st floor condo. This is the only condo with a large outdoor living room and tropical gardens. Relax on the outdoor sofa and indulge in a glass of wine and a grilled filet while the fire pit and lighted palms give you ambiance. This renovated unit is walking distance to all.......read more

Studio
Sleeps 4
Condo

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Updated Beach Style Condo at Sand Cay with Great Ocean Views.

Longboat Key Condo - 4.79348 4.8 Star Review

Current COVID-19 situation:
The County restrictions include numerous cleaning and other requirements for your safety. Our own internal requirements meet or exceed what is required by the County/CDC. Please also note that our condo has its own separate entrance, there are no enclosed corridors or hallways to get to the unit, it is accessible by o.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Hidden Bay/Beach Paradise

Longboat Key Private vacation home - 4.89706 4.9 Star Review

Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis cou.......read more

4 Bedroom(s)
Private vacation home

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2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)

Longboat Key Condo - 4.90278 4.9 Star Review

Sand Cay resort is open using the industries best practices and guidelines to ensure that all CDC sanitizing guidelines are carried out completely. Moving forward we will use only a EPA-registered product, qualified for use against against SARS-CoV-2, the novel coronavirus that causes COVID-19. This process takes about 45 minutes and we will be cha.......read more

2 Bedroom(s)
Sleeps 4
Condo

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1st Floor Home Away from Home - Steps to Beach - Pool

Longboat Key Condo - 5.0 5.0 Star Review

A very warm welcome to your beautiful, home away from home on this Island Paradise!

This gorgeous location is truly one of the most relaxing places on the planet, and we know that you are just going to love it!

With views of the gorgeous Gulf of Mexico from the living areas, Master Bedroom and Lanai of our fabulous first floor apartm.......read more

2 Bedroom(s)
Sleeps 6
Condo

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THE BEACH, condo #107, PRIVATE BEACH OPEN

Longboat Key Apartment - 4.85185 4.9 Star Review

Studio, sleeps 4, full kitchen with ss appliances and granite countertops, 1 ba, private beach front patio, heated beach front swimming pool, private beach access to uncrowded pure white sand beach, complimentary lounge chairs & umbrellas, laundry, LCD flat-screen TVs, picnic area with BBQ grill, complimentary parking, unit on first floor. Long.......read more


Cedars East #528: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6

Longboat Key Private vacation home - 5.0 5.0 Star Review

RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious town homes that are perfect for families or couples. There is something to suit every mood a.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.

Longboat Key Cottage - 4.61905 4.6 Star Review

Beachfront cottage that is located directly on the Gulf of Mexico and the only thing that is between you and your beach front cottage, are sea oats, palm trees and sand dunes. We are a premier and private beach holiday spot. The property is secluded and private and you are assured a hassle free beach front holiday.

The cottage has a full kit.......read more

2 Bedroom(s)
Sleeps 6
Cottage

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Spacious third floor condo with Gulf views, screened-in porch, and shared pool!

Longboat Key Condo

Key Gulf View 302

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

**This unit requires an HOA application and will perform a background check on the reservation holder**

Spread out and relax in this lavish Gulf side condo - you can see it.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Charming 2/2 Beach House LBK 5 Min walk to Beach

Longboat Key Private vacation home

OUTSTANDING LOCATION on LONGBOAT KEY, only a 5-minute walk to the gorgeous beach on the Gulf of Mexico!

This charming beach house is 1,404 sq ft with 2 bedrooms, 2 bathrooms, large deck and outdoor area with fire pit.
The main living area is on the 2nd floor, which you can access by wooden stairs from the front and back of the house.
.......read more

2 Bedroom(s)
Sleeps 5
Private vacation home

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Condo,private beach,kayak in bay

Longboat Key Condo

Enjoy your morning coffee while sitting on back patio watching the traffic of Sarasota Bay. Kayaks for use, private beach. Beautiful bike path that takes you to Bradenton or Sarasota. Sunsets are amazing. .......read more

Studio
Sleeps 1
Condo

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Beachcomber unit 401

Longboat Key Condo - 5.0 5.0 Star Review

Our building is located on the beach, this unit has an ISLAND view.
Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.
Please note: We do not allow Sunday or holiday arrivals and require a 7 night min.......read more

Studio
Sleeps 4
Condo

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

Longboat Key Villa - 5.0 5.0 Star Review

NEW LISTING!

Perfect place for a beach getaway! Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, shops, restaurant, mini market, bike rental shop and more. Nestled in a quiet are, perfect to relax or work remotely. We offer Super Fast 600MBPS internet!

Centrally located in Longboat key, condo features a ful.......read more

2 Bedroom(s)
Villa

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NEW! Gulf Getaway w/ Porch + Direct Beach Access!

Longboat Key Condo - 5.0 5.0 Star Review

Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in the Silver Sands Gulf Beach Resort. Boasting a fully equipped kitchen and nestled on the ground floor, this beach escape provides all of the essential comforts paired with convenience for a relaxing stay. Tee off at the green in the.......read more

Studio
Sleeps 4
Condo

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Find Affordable Longboat Key Hotels & Vacation Rentals

Plan your Longboat Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Longboat Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.


Vacation Rentals Nearby Tampa Bay Destinations

Find nearby vacation rentals and some of the Best Hotels with cheap rates in Longboat Key, FL for you visit to the area, all a short drive to Longboat Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.


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