Longboat Key, Sarasota Vacation & Condo Rentals
Book Places to Stay and Vacation Home Rentals in Longboat Key Sarasota Directly Online Here and Save!
We have many choices for Longboat Key Sarasota Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Sea Grape Inn #4- BEACHFRONT Property
Longboat Key Apartment 
4.7
*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
Sea Grape Inn #5- BEACHFRONT Property
Longboat Key Apartment 5.0
*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)
2 Bath(s) Sleeps 6
Sea Grape Inn #7 - BEACHFRONT Property
Longboat Key Apartment 4.9
*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
Standalone Unit at Little Gull Resort. Amazing Sarasota Bay View! Walk to Beach.
Longboat Key Condo 4.0
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)
2 Bath(s) Sleeps 8
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)
2 Bath(s) Sleeps 6
Longboat key paradise townhome with an attached double deep garage.
Longboat Key Private vacation home 4.5
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)
2 Bath(s) Sleeps 7
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
Studio
4 Bath(s) Sleeps 5
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)
2 Bath(s) Sleeps 6
On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental
Longboat Key Condo 5.0
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
Luxurious Beachfront Villa with Private Pool
Longboat Key Condo 4.9
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)
3 Bath(s) Sleeps 8
Awesome Winter Getaway-Four Winds Beach Resort condo on the Gulf of Mexico
Longboat Key Condo 4.7
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
1 Bedroom(s)
1 Bath(s) Sleeps 4
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
2 bedroom 2 bath beach condo Rental
Longboat Key Condo
July 6 thru 13 Week 27- UNIT 402
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 queen size sleep sofa in the living room. Full Kitchen and washer and dryer in the uni.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
A couple’s retreat. Condo Nestled in quiet area. Walk to beach & shops.
Longboat Key Villa 5.0
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)
NEW! Gulf Getaway w/ Porch + Direct Beach Access!
Longboat Key Condo 5.0
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
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)
2 Bath(s) Sleeps 6
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
A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.
Longboat Key Cottage 4.6
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)
1 Bath(s) Sleeps 6
Only requests for 9/12/22-11/12/22 time frame will be considered at this time!
Longboat Key Private vacation home 4.9
At this time, We are unable to accept requests for next winter (Jan-April 2023) as we give right of first refusal to our current tenants. Please check back with us in June for that time frame. Our private waterfront residence is surrounded by the topical beauty of the Gulf of Mexico and Millar/Sarasota Bay. This updated Longboat Key beach/boater\.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 5
1st Floor Home Away from Home - Steps to Beach - Pool
Longboat Key Condo 5.0
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)
2 Bath(s) Sleeps 6
Amazing Beachfront 2B/2B in Longboat Key
Longboat Key Condo 4.8
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)
2 Bath(s) Sleeps 6
Beachcomber unit 401
Longboat Key Condo 5.0
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
1 Bedroom(s)
1 Bath(s) Sleeps 4
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
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 Isla.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Longboat Key Condo 4.8
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)
2 Bath(s) Sleeps 6
Longboat Key Waterfront Getaway
Longboat Key Private vacation home 5.0
Single story living at its best. This newly renovated 2 bed /2 bath home features upscale finishes and materials on a deep water canal with 50 \'dock, kayak ramp, gas fire pit and heated splash pool.
This inviting, one-story home features a modern open floor plan that integrates harmoniously with the outdoors. A beautiful 420 Square foot glass .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Inn on the Beach 2207
Longboat Key Condo 4.7
Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area.
Our guests have access to the beautiful private beach, pool and hot tub area only. Resort amenities (golf, dining, tennis, room & maid service or fitness) are private and not includ.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Cedars East #519: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home 5.0
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)
3 Bath(s) Sleeps 6
UNIQUE LONGBOAT KEY OASIS!
Longboat Key Condo 5.0
We are please to offer our lovely, artfully ornamented and spacious 2BR/2BA second floor unit on a Longboat Key. Functional and decorated with love and care throughout this gem is located in small condo community (only 7 units) and offers a tranquil environment with magnificent sunrise views of the Sarasota Bay. Freshly painted in a soothing beach-.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Spacious 2Bdrm Longboat Key Condo
Longboat Key Condo 5.0
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)
3 Bath(s)
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)
2 Bath(s) Sleeps 10
PARADISE FOUND* PEACEFUL & ELEGANT UPDATED *CANAL HOME *WALK TO BEACH* NEW BIKES
Longboat Key Private vacation home 5.0
*****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
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Longboat Key Condo 4.8
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
*** OCEAN FRONT SPECIAL *** From $99/night
Longboat Key Condo 4.6
*** OCEAN FRONT SPECIAL *** From $99/night
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Longboat Key - Ocean Front Condo
~ DIRECT BEACH FRONT CONDO ~
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Beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get.
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We offer the lowest rates in this resort c.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 3
Beach Front Condo
Longboat Key Condo 5.0
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)
Whitney Beach #336: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 4
Longboat Key Condo 5.0
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