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Longboat Key, Sarasota Vacation & Condo Rentals

Book Your Longboat Key Sarasota Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Longboat Key Sarasota Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Longboat Key Sarasota Florida.

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

Longboat Key Private vacation home Star 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)
2 Bath(s) Sleeps 8


Vacation Rental


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

Longboat Key Condo Star 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 her.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


Sea Grape Inn #4- BEACHFRONT Property

Longboat Key Apartment Star 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)
2 Bath(s) Sleeps 4


Vacation Rental


Beach Breeze: Stunning waterfront 2 BR / 2 BA condo.

Longboat Key Condo

Welcome to Beach Breeze! This immaculate 2-bedroom, 2-bath second-floor condo located in the highly sought-out community of Windward Bay has views of the Gulf in every direction!

The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


Silver Sands #233: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 4.7 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

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


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

Longboat Key Condo Star 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 b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


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

1 Bedroom(s)
2 Bath(s) Sleeps 1


Vacation Rental


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

Longboat Key Private vacation home Star 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)
2 Bath(s) Sleeps 8


Vacation Rental


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

Longboat Key Condo Star 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

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Canal front cottage, walking distance to sandy Gulf

Longboat Key Private vacation home Star 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)
1 Bath(s) Sleeps 6


Vacation Rental


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

Longboat Key Private vacation home Star 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

Studio
1 Bath(s) Sleeps 2


Vacation Rental


Silver Sands #241A: HOTEL / 1 BA Resort on Longboat Key by RVA, Sleeps 2

Longboat Key Apartment Star 4.5 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
1 Bath(s) Sleeps 2


Vacation Rental


Sea Grape Inn #7 - BEACHFRONT Property

Longboat Key Apartment Star 4.9 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- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 2-Twin Beds.
Situated in this idyllic resort comprised of eight un.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


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

Longboat Key Private vacation home Star 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)
2 Bath(s) Sleeps 6


Vacation Rental


Beach front condo with Gulf sunset views

Longboat Key Condo

Immaculate condo boasts beautiful Gulf views. Enjoy the sunset every night from the screened in lanai, or walk out to the 1400\' private Bayport beach. Bayport\'s lush grounds are flawlessly maintained with a wide variety of native trees and shrubs. Amenities include four immaculately maintained Har-Tru clay tennis courts, a Junior Olympic sized .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


Casa Del Mar: 3 BR / 2.5 BA Home on Longboat Key by RVA, Sleeps 6

Longboat Key Private vacation home Star 4.5 Star Review

Enjoy island-style vacations at the Casa del Mar Home. Located on the north end of the exclusive island of Longboat Key, this vacation home specializes in serenity with a natural ambiance. The Casa del Mar Home is a raised building, which allows for beautiful views of foliage and the canal. Some of the amenities you’ll enjoy are: comfortable furn.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


ON the Beach, Covert II Condominium

Longboat Key Condo Star 4.6 Star Review

On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service within the US, 2 TV\'s with cable service, Wi-Fi high speed internet, Screened Gulf front Lanai with table and chairs for a great dining view. second floor unit near the elevator. Coin operated washer / dryer available on each floo.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Stunning sunset views; Beachfront condo on central Longboat Key

Longboat Key Condo Star 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)
2 Bath(s) Sleeps 6


Vacation Rental


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

Longboat Key Condo Star 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)
2 Bath(s) Sleeps 6


Vacation 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

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Silver Sands #232: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 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

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


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

Longboat Key Condo Star 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)
1 Bath(s) Sleeps 6


Vacation Rental


Whitney Beach #336: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 5.0 Star Review

RVA invites you to experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with next door shopping at Whitney Beach Plaza, this property offers this two-bedroom, two-bathroom spacious end unit villa. Imagine spending your days lounging by the community pool, enjoying a game of tennis, or sipp.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


Outrigger Resort #8: 1 BR / 1 BA Condo on Longboat Key by RVA, Sleeps 2

Longboat Key Condo Star 4.4 Star Review

RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger Resort. The Outrigger grounds offer coin-operated laundry facilities, BBQ areas, and direct beach access. Relax by the heated community pool, take a stroll along the romantic beaches, or enjoy a short drive to the world famous St.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Rental


Silver Sands #241: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key Condo Star 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

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Longboat Key Condo Star 4.8 Star Review

Welcome to our Ground floor BEACHFRONT condo unit #119 at the beautiful Sand Cay Beach Resort on Longboat Key!

Magnificent renovated (January 2022) condo with an open 1,132 sq. ft. floor plan, 2 bedrooms, 2 full bathrooms, full kitchen, a large living and dining room as well as a separate sitting room with a queen sleeper sofa. Condo sleeps .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


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

Longboat Key Villa Star 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)
1 Bath(s)


Vacation Rental


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

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Rental


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)
2 Bath(s) Sleeps 4


Vacation 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)
2 Bath(s) Sleeps 5


Vacation Rental


Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Longboat Key Condo Star 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)
2 Bath(s) Sleeps 6


Vacation Rental


Sea Duced: Beachfront townhouse with a private heated pool located on Longboat K

Longboat Key Private vacation home

Welcome to Sea Duced! Rarely available beachfront 3 bedroom, 3 bath townhouse with a private indoor pool located on the stunning, Longboat Key.

Designed by Sarasota School of Architecture co-founder Tim Seibert to capture breathtaking views of the white sandy beach and the triumphant blue waters of the Gulf of Mexico.

The nearly 3,0.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


Beach Front Condo

Longboat Key Condo Star 5.0 Star Review

Longboat Key second floor beach-front condo, with two bedrooms, additional bonus room, two full bathrooms, breathtaking views, and a private pool. The condo was fully renovated and is completely updated with new appliances. Large lanai with an unobstructed view of the Gulf of Mexico, spectacular sunset. New hurricane-rated sliding doors and new wi.......read more

3 Bedroom(s)
2 Bath(s)


Vacation Rental


Gulf Beach Resort - B

Longboat Key Private vacation home

Unit Features: 1-bedroom, 1-bathroom unit in the Orange Building Layout Note: Please note, the front door to unit 245 opens into a bedroom space before proceeding into the living areas. We kindly ask guests to take this layout feature into consideration when making their travel selections. View: Pool/Gulf View Bedding: 1 King, Sleeper Sofa Resort F.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Rental


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

Longboat Key Condo Star 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)
2 Bath(s) Sleeps 4


Vacation Rental


Beautiful studio unit at resort, sleeps 4

Longboat Key Apartment

Gulf Tides of Longboat Key offers a number of recreational opportunities and a superb location near the cities of Tampa, Sarasota, and Fort Myers. At the resort\'s beach, you can enjoy all types of water activities. The resort features a lighted tennis court, heated outdoor pool, bikes, shuffleboard, and barbecue grills. Close by, both Sarasota and.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Rental


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