Longboat Key Florida Vacation Rentals, Hotels & Resorts

Search hundreds of Vacation Rentals, Condos and Homes in Longboat Key, Florida

Book Your Vacation Homes Directly Online Here and Save!

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.

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

View Rental


Longboat key paradise townhome with an attached double deep garage.

Longboat Key Private vacation home - 4.52273 4.5 Star Review

This beautiful townhouse house built in the style of the west coast, has been furnished recently with skilful whimsical, bohemian style in the warm colors of pinks and blues. The house is spread over three levels on the first floor and will welcome you with beautiful and soft sofas (bed) positioned towards a veranda terrace directly overlooking th.......read more

2 Bedroom(s)
Sleeps 7
Private vacation home

View Rental


Cozy Canal Condo w/ boat dock and walk to beach

Longboat Key Condo

Enjoy the complete island experience in this one bedroom, one bath, canal front condo, with a private boat dock (21\' total length). We\'re located on a quiet street just half block from Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserve.

Relax on your waterfront patio, perfec.......read more

Studio
Sleeps 2
Condo

View Rental


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

View Rental


Right on beautiful Sarasota Bay !! BEAUTIFUL VIEWS 2/2!

Longboat Key Condo - 5.0 5.0 Star Review

Want a beautiful view of the Sarasota Bay from a luxury condo on Longboat Key? This two bedroom second Floor unit with Tommy Bahama Inspired Décor is perfect for a peaceful getaway. This condo is perfect for couples or small families looking to get away from it all.
We hope you have the opportunity to enjoy some of the unique features of this be.......read more

2 Bedroom(s)
Sleeps 4
Condo

View Rental


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

View Rental


Standalone Unit at Little Gull Resort. Amazing Sarasota Bay View! Walk to Beach.

Longboat Key Condo - 4.0 4.0 Star Review

In the middle of April, the Florida weather is warm, the ocean is cool and blue, and the beach is all yours. We are pleased to offer our beautiful 4-bedroom, second-story timeshare for week 16 of 2018 (April 21st to the 28th). Unit #16 at Little Gull Cottages has spectacular, unencumbered views of the Sarasota Bay and is only a five minute walk t.......read more

4 Bedroom(s)
Sleeps 8
Condo

View Rental


Unit is a wow take a peek LATE Sept sale

Longboat Key Condo - 4.9697 5.0 Star Review

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 wicker furniture, silly beach artifact.......read more

Studio
Sleeps 6
Condo

View Rental


Sea Grape Inn #4- BEACHFRONT Property

Longboat Key Apartment - 4.72222 4.7 Star Review

*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.
A first floor 2 bedroom 2 bath condo that offers a view o.......read more

2 Bedroom(s)
Sleeps 4
Apartment

View Rental


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

View Rental


Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome

Longboat Key Private vacation home - 4.74545 4.7 Star Review

*** Contact owner for current availability and discounts! ***

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. .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


Haven on Hughes: Pool home minutes from Longboat Key Beach!

Longboat Key Private vacation home

Welcome to Haven on Hughes! This one-of-a-kind 3-bedroom, 2-bath, two-story spacious pool home is located on the Historic North End of gorgeous Longboat Key.

The location of Haven on Hughes is perfect if you enjoy the feeling of a quiet seaside village with easy access to a variety of activities and conveniences.

BEACHES: 7 blocks fr.......read more

3 Bedroom(s)
Sleeps 10
Private vacation home

View Rental


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

View Rental


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

Longboat Key Condo - 4.88571 4.9 Star Review

RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambian.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Beach Castle Resort #14: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo - 4.80952 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

Studio
Sleeps 4
Condo

View Rental


On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental

Longboat Key Condo - 4.95652 5.0 Star Review

The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Cedars East #607: 2 BR / 2 BA Townhome on Longboat Key by RVA, Sleeps 8

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 8
Private vacation home

View Rental


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

View Rental


Inn on the Beach 1307

Longboat Key Condo - 4.75 4.8 Star Review

PLEASE NOTE: From November 19, 2022 through April 22, there is a 7 night minimum, Saturday to Saturday Stay Only.
FL Vacation Connection looks forward to welcoming to this luxury beachfront getaway located on the southern tip of Longboat Key, tucked behind the gates of the Longboat Key Club and Resort, known for its private beaches and po.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Love the beach? Tennis? Swimming? This great family friendly retreat has it all!

Longboat Key Private vacation home - 4.94595 4.9 Star Review

Spacious 2400 square foot elevated home (there are 16 steps to enter and exit) featuring wide open floor plan with vaulted ceilings, huge living/kitchen/dining room.
Fully equipped kitchen featuring large single bowl stainless steel sink, huge quartz island work space, double oven and seating for four at the counter.
DISH T.V. and whole hom.......read more

4 Bedroom(s)
Sleeps 9
Private vacation home

View Rental


Stunning sunset views; Beachfront condo on central Longboat Key

Longboat Key Condo - 5.0 5.0 Star Review

Private Condo located on second floor at Tiffany Plaza on Longboat Key. Second floor accessible only by security code elevator or stairs requiring key. Our condo has two bedrooms, both with a king bed, and two full bathrooms. Private balcony overlooking Gulf of Mexico, can be accessed through living room or master bedroom.

Condo Association.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


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

View Rental


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

View Rental


Cedars East #810: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 4

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 townhomes that are perfect for families or couples. There is something to suit every mood at.......read more

2 Bedroom(s)
Sleeps 7
Private vacation home

View Rental


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

View Rental


Island Paradise: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 8

Longboat Key Private vacation home - 4.0 4.0 Star Review

RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key\'s sunshine. This home offers privacy un-matched with a tropical caged pool area offering a heated hot tub and pool. This large home seems to never end, around every corner there is comfortable spot to sit and read a book or watch your favorite show o.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

View Rental


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

View Rental


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

View Rental


Longboat Key Club!! Direct Beachfront!!

Longboat Key Condo - 4.66667 4.7 Star Review

Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maxim.......read more

Studio
Condo

View Rental


Silver Sands #252: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo - 4.64286 4.6 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

View Rental


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.


Search for Vacation Rental Homes or Hotels

           
Best Prices Booking


Vacation Places To Stay We have chosen to partner with Booking.com to offer travelers the best choices for vacation properties - No Booking Fees, Last Minute Room Availability, 2,146,000+ hotels, apartments, villas, condo rentals and more....

Rentals in Longboat Key, FL

Don't know Where To Stay? Select your destination and search for discount accommodations.

If you don't see your travel destination, just type it in the box and search for hundreds of Hotels, Resorts, Motels, Homes, Villas or Condos and more!

Cheap Hotels Longboat Key, FL

Trying to save money on your vacation? VacationPlacesToStay.com has great deals and low prices on vacation rentals & hotels, Best Price Guaranteed.

Save when you book directly online for last minute deals with 3 to 5 Star Resorts, Inns, Hotels and more!

© Reservations Direct, Inc. - Vacation Rentals, Resorts & Hotel Accommodations

About Us - Privacy - Top Destinations - Best Vacation Spots - Car Rentals