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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.
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
Gulf Front, luxury condominium in beautiful Long Boat Key, FL
Longboat Key Condo
- 
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
On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental
Longboat Key Condo
- 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
Beach condo is steps to a beautiful pool, beach with stunning views of sunset.
Longboat Key Condo
- 5.0 Star Review
This property has two bedrooms, two baths, and opens onto a screened in lanai. It is newly renovated with an open kitchen, office, and living room with views of the ocean. It is fully stocked with everything you need for a peaceful stay at the beach........read more
2 Bedroom(s)
Sleeps 6
Condo
Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
Longboat Key Condo
- 4.9 Star Review
Your safety is our top priority.
This unit is professionally cleaned using EPA registered product to combat Covid-19. In addition the unit is sanitized using a fogging process that kills 99.99% of bacteria and viruses following CDC & Florida guidelines.
Enjoy this beautiful, renovated Gulf-front sunny unit with vaulted ceilings, spectacul.......read more
2 Bedroom(s)
Sleeps 6
Condo
Tarawitt Home: 3 BR / 3 BA House on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 5.0 Star Review
RVA presents this spacious vacation home. The Tarawitt Home, is located on a secluded road at the northern tip of Longboat Key. This vacation home has all the amenities needed for a relaxing vacation. With three bedrooms, three baths, a sleeper sofa, and a separate family and game room, the Tarawitt Home can house up to eight persons comfortably. T.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
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
Studio
Sleeps 3
Private vacation home
NEW! Gulf Getaway w/ Porch + Direct Beach Access!
Longboat Key Condo
- 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
Newly Remodeled! Directly Across from Beach ~ Condo
Longboat Key Condo
- 4.9 Star Review
The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. The island has very little commercialization and there are no fast food chain, but yet still has all the conveniences wanted.
No crowds, only a peaceful and relaxing beach that will feel as if it is your piece of heaven. Th.......read more
Studio
Sleeps 2
Condo
NO REGRETS Bright beautiful sunny home. Elevator whisks U up to 2nd floor living
Longboat Key Private vacation home
- 4.9 Star Review
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, WHICH PROVIDES FOR EASY ACCESS FROM beside the GARAGE TO ALL THE LIVING AREAS!
OVER AN ACRE OF PARK AND LAWNS AROUND YOU FOR SAFE.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Casa Del Mar: 3 BR / 2.5 BA Home on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 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 furnis.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
client said view crazy Aug sale arrive 26- leave 31 had cancellation
Longboat Key Condo
- 4.9 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
Beachcomber unit 401
Longboat Key Condo
- 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
On the Beach - 1 week rental Long Boat Key ( Sarasota barrier Island )
Longboat Key Condo
June 29 thru July 6 this is week 26 ONLY Week 26 & 27- UNIT 402 are both available, discount if you book both weeks
3 PM Saturday
Enjoy partial views of the Gulf from a two-bedroom apartment with accommodation for up to six guests. This includes a king size bed in the master bedroom, two twin beds in the guest bedroom and a.......read more
2 Bedroom(s)
Sleeps 6
Condo
Luxurious Beachfront Villa with Private Pool
Longboat Key Condo
- 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
A couple’s retreat. Condo Nestled in quiet area. Walk to beach & shops.
Longboat Key Villa
- 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
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
LBK Getaway
Longboat Key Condo
Welcome to Paradise at LBK Getaway! Great opportunity to stay at an exquisite 2-bedroom, 2-bathroom villa style home in the coveted north end of Longboat Key. Just feet away from the crystal blue gulf water and beautiful pristine sandy beaches. Spend the day catching a wide variety of fish on the fishing piers or building sand castles in the sand. .......read more
Updated Beachfront Studio w/ Sparkling Pool, Breezy Patio & Modern Kitchen
Longboat Key Private vacation home
- 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
Cedars East #519: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 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
Sea Grape Inn #5- BEACHFRONT Property
Longboat Key Apartment
- 5.0 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 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Beautifully remodeled and upgraded; .......read more
2 Bedroom(s)
Sleeps 6
Apartment
Cedars East #528: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 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
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
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Longboat Key Condo
- 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)
Sleeps 6
Condo
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)
Sleeps 4
Condo
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)
Sleeps 6
Private vacation home
Silver Sands #235: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 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
2 Bedroom(s)
Sleeps 6
Condo
Amazing Beachfront 2B/2B in Longboat Key
Longboat Key Condo
- 4.8 Star Review
October and November 2021 are still available with Deep Discount Prices!
Wonderful Beachfront condo in magnificent Longboat key. You will Love the beautiful private Balcony with sensational beachfront views of turquoise Gulf waters. This unit is on the second floor with an elevator for easy access. Space is a roomy 1175 sqft with a full-.......read more
2 Bedroom(s)
Sleeps 6
Condo
Silver Sands #255S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 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
2 Bedroom(s)
Sleeps 6
Condo
Awesome Winter Getaway-Four Winds Beach Resort condo on the Gulf of Mexico
Longboat Key Condo
- 4.7 Star Review
1 bedroom 1 bathroom full kitchen furnished condo at the beach. Offering 1, 2 or all 3 weeks beginning January 16 through February 6, 2021, check in and check out on each Saturday. All amenities included in room WIFI, cable TV, hot tub, heated pool, steps from the white sands of the Gulf of Mexico, tennis courts, shuffleboard, bicycles, grilling .......read more
Studio
Sleeps 4
Condo
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.
Rentals in Longboat Key, FL
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