Island Properties
Jennette Properties offers luxury vacation rentals throughout all the islands on the Gulf coast including the barrier islands Longboat Key, Lido Key, Siesta Key, Casey Key and much more. Our beautiful vacation rental properties are surrounded by top rated beaches along the Gulf.
If you’re looking for the best beach vacation rentals in Florida, check our inventory of properties available.
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597 Yawl Lane 597 Yawl Lane, Longboat Key, FL
Single Family Home Longboat Key area Island community
If you like to be on the water this newly upgraded Country Club Shores home has outstanding views of Sarasota Bay. Be the first to experience this comfortable open-concept home, one in from the bay, with fabulous water views that begin as soon as you step in the front door. It’s newly furnished and decorator |
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1179 Morningside Place 1179 Morningside Place, Sarasota, FL
Single Family Home Lido Key / St. Armands Circle area Island community
Absolutely gorgeous turnkey furnished home on Lido Shores. This turnkey furnished two story house has a whopping 3,211 square feet, four bedrooms, three bathrooms, two master suites, living room/kitchen/breakfast nook combination, formal living area, laundry room with plenty of counter space and a utility sink, vaulted ceilings, three bedrooms on the first floor and one |
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3804 Gulf of Mexico Drive #B-402 3804 Gulf of Mexico Drive #B-402, Longboat Key, FL
Condo Longboat Key area Island community
LONGBOAT KEY…Lovely 2 bedroom 2 bath penthouse located on the top floor in Building B directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile and marble. Split floor plan, master suite with a king size bed and the guest room can be used as |
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1250 N. Portofino Drive #107 1250 N. Portofino Dr. #107, Siesta Key, FL
Condo Siesta Key area Island community
This freshly painted 2 bedroom, 2 bath condo is conveniently located on the ground floor next to the club house and features new appliances, granite counter tops and ceramic flooring. The bedrooms are carpeted with a Queen size bed in the Master, a walk in closet plus a full wall length closet. The guest bedroom |
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435 L’Ambiance Drive #402 435 LAmbiance Drive #402, Longboat Key, FL
Beach Condo Longboat Key area Island community
LUXURY LIVING…behind the gates of LONGBOAT KEY CLUB. Spacious two bedroom, 3 bath condo with a FABULOUS VIEW OF THE GULF OF MEXICO and the SARASOTA BAY FRONT. A huge wrap around balcony to enjoy your morning coffee and beautiful sunsets every night. Conveniently located a short distance from restaurants and shopping on St. Armand’s |
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1257 S. Portofino Drive #104 1257 S. Portofino Drive #104, Sarasota, FL
Condo Siesta Key area Island community
Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has added new bedding, an air mattress available for guests, a new coffee |
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131 Garfield Drive, 4C 131 Garfield Drive #4C, Sarasota, FL
Condo Lido Key / St. Armands Circle area Island community
Lovely “penthouse” unit in The Riviera of Lido Beach with two bedrooms two bathrooms located in the heart of Lido Key. It is a few steps from the beach, and the Lido Pavilion. Nicely furnished with all the comforts of home and this unit has a large porch that overlooks the tree tops with a |
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1485 Gulf of Mexico Drive #109 1485 Gulf of Mexico Drive #109, Longboat Key, FL
Condo Longboat Key area Island community
Gorgeous beach front condo in the sought after Longboat Key community The Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized |
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1387 MOONMIST DRIVE 1387 MOONMIST DRIVE, Sarasota, FL
Villa Siesta Key area Island community
Beautiful furnished villa in Polynesian Gardens available to rent. The immaculately maintained, neat as a pin villa has fresh paint, a split floor plan, living room/dining room combination, plantation shutters, crown molding and 1,381 square feet. The property has 2 bedrooms, 2 bathrooms, a one car garage with a utility sink and two outdoor living |
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2901 Casey Key Road 2901 Casey Key Road, Nokomis, FL
Beach House Casey Key area Island community
Welcome to Villa di Tramonto, house of sunsets, gorgeous remodeled 4 bed 4.5 bath home complete with private beach on the Gulf of Mexico. Stunning views on all levels, this magnificent home is decorated in elegant coastal furnishings. Entering the front door from the gated and beautifully foliaged entryway immediate ocean views are offered along |
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2109 Gulf of Mexico Drive #1101 2109 Gulf of Mexico Drive #1101, Longboat Key, FL
Condo Longboat Key area Island community
Stunning Condo on Long Boat Key with gorgeous Sunset views…Right on Sunset Beach !! 2 oversized lanai terraces allow privacy and access right down to the turquoise water and pristine sandy beach. Tastefully decorated ,complete Turnkey Furnished S.W corner 2 bed,2 bath Condo with Washer and Dryer.. Situated on the South end of Long Boat |
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3240 Gulf of Mexico Drive #B303 3240 Gulf of Mexico Drive B303, Longboat Key, FL
Beach Condo Longboat Key area Island community
Beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Enjoy your morning coffee while sitting on the screened lanai |
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1925 Gulf of Mexico Drive #208 1925 Gulf of Mexico Drive #208, Longboat Key, FL
Beach Condo Longboat Key area Island community
Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Master Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis |
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2425 Gulf of Mexico Drive, #4E 2425 Gulf of Mexico Drive, #4E, Longboat Key, FL
Beach Condo Longboat Key area Island community
LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist’s private collection for your enjoyment. Granite counters |
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6157 Midnight Pass Road G-22 6157 Midnight Pass Rd. G-22, Sarasota, FL
Condo Siesta Key area Island community
This beautiful 2 bedroom 2 bath condominium is located in popular Bay Oaks complex on #1 rated Siesta Key! Enjoy your two level condo complete with lower level kitchen, dining and living room and two master suites upstairs each with its own full bathroom. Bay Oaks features tennis courts, swimming pool, fishing pier, picnic tables |
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1 Ben Franklin Drive #22 1 Ben Franklin Drive #22, Sarasota, FL
Condo Lido Key / St. Armands Circle area Island community
Beautiful rental condo available in the sought after community of St. Armand’s Tower North. This is the best location on Lido Key!! Nicely decorated to put you in a vacation state of mind. The condo has two bedrooms plus an extra murphy bed for overflow guests, two bathrooms, living room/dining room combination, breakfast bar, all |
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1945 Gulf of Mexico Dr. #307 1945 Gulf of Mexico Dr. #307, Longboat Key, FL
Beach Condo Longboat Key area Island community
GREAT LONGBOAT KEY LOCATION…This two bedroom, two bath condo has everything you’ll need to feel right at home. A southern exposure offers a partial view of the Gulf of Mexico from the screened balcony. HD flat screen TV’s, wireless internet. Seaplace offers 2 swimming pools, Har-Tru tennis courts and a fitness center. A very short |
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3434 Casey Key Road 3434 Casey Key Road, Nokomis, FL
Beach House Casey Key area Island community
Fabulous Gulf to Bay property on beautiful Casey Key, one of the most unusual keys on the West Coast of Florida. Immaculately kept three bedroom home with a dock on the bayside of Casey Key. Cabana across the street overlooks the Gulf of Mexico. Beautiful views from the living room across the pool to the |
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130 Island Circle 130 Island Circle, Sarasota, FL
Single Family Home Siesta Key area Island community
Located on Palm Island on Siesta Key, this whimsical 3 bedroom, 3 bath ranch home will amaze and delight your senses! The attention to detail and quality of finishes is second to none in this island home on Siesta Key’s Grand Canal. The gorgeous tropical setting brings you to the entrance foyer with a 10 |
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4540 Gulf of Mexico Drive PH2 4540 Gulf of Mexico Drive PH2, Longboat Key, FL
Condo Longboat Key area Island community
Rarely available tranquil 2 bed/2 bath corner unit condo with full bay views at desirable Windward Bay! This light and bright condo is the perfect place to spend your season in the sun in a quiet community directly across the street from the sparkling Gulf of Mexico waters and white sandy beaches of Longboat Key. |
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800 S Blvd of Presidents #12 800 S Blvd of Presidents #12, Sarasota, FL
Villa Lido Key / St. Armands Circle area Island community
SARASOTA ST ARMAND’S CIRCLE LIDO KEY Welcome to the EMBASSY VILLAS. This stylish newly renovated corner unit Townhouse is absolutely Perfect for your stay on LIDO KEY this SEASON. TWO BLOCKS from Lido Beach and the Lido Public Pool. PRIME Location walking distance to St. Armand’s Circle where you can enjoy the many world class |
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620 Buttonwood Drive 620 Buttonwood Drive, Longboat Key, FL
Single Family Home Longboat Key area Island community
LONGBOAT KEY SARASOTA This beautifully remodeled home is light and bright with a spacious OPEN spit floor plan. Located in the tree lined island neighborhood of Buttonwood Harbour. A Wonderful floor plan with huge double sized Master suite and a second Master Suite both with King bed, pool access and views. Master Double Suite has |
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106 Beach Road 106 Beach Road, Sarasota, FL
Beach House Siesta Key area Island community
South Beach Miami Style House right on Siesta Beach! Ultra luxurious rental available for annual or longer term seasonal rental. Available immediately! Just steps away from Siesta Key Village and all the amenities it has to offer. On every level of this open floor plan home are unlimited views of the incomparable sand on Siesta |
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1100 Ben Franklin Drive, #305 1100 Ben Franklin Drive #305, Sarasota, FL
Beach Condo Lido Key / St. Armands Circle area Island community
Beautifully decorated condo in Sarasota Florida right on Lido Beach. One bedroom, with one and one half bathrooms located a short walk from St. Armands Circle. Lido Surf and Sand is located right on the beach with a beautiful pool and spa. One month minimum. |
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779 N Manasota Key Road 779 N Manasota Key Road, Englewood, FL
Single Family Home Englewood area Island community
Come and escape to your own private 1.76 acre oasis of Gulf of Mexico beach frontage and Intercoastal Waterway. Have the best of both worlds to enjoy. This 2 story homes offers magnificent beach ocean views and never seen before sunsets from every bedroom, dinning and living room… This secluded gated north peninsula of North |
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1975 Gulf of Mexico Drive, #208 1975 Gulf of Mexico Drive, #208, Longboat Key, FL
Beach Condo Longboat Key area Island community
SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the master suite. Master bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, |
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1906 Harbourside Drive #301 1906 Harbourside Drive #301, Longboat Key, FL
Condo Longboat Key area Island community
End unit townhouse in Fairway Bay, with a boat dock. All new decorating in this light and spacious unit that has a view of the canal. Lots of windows and two stories with skylights giving the unit loads of light. Living room is two stories with a vaulted ceiling. All new decorating, two master suites |
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1257 S Portofino Drive #106 1257 S Portofino Drive #106, Sarasota, FL
Condo Siesta Key area Island community
Attention Island Lovers – Crescent Beach is across the street and a boat dock is included in your rental! Hop on your boat in the protected canal and take it to the Intracoastal Waterway where you will find a lunch or dinner spot at one of the many waterfront restaurants. This is a boater and |
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2109 Gulf of Mexico Drive #1402 2109 Gulf of Mexico Drive #1402, Longboat Key, FL
Beach Condo Longboat Key area Island community
LONGBOAT KEY…SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. |
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1125 Gulf of Mexico #403 1125 Gulf of Mexico #403, Longboat Key, FL
Condo Longboat Key area Island community
SEASONAL/ANNUAL Beachplace is one of Longboat Key’s most popular vacation rental resorts on the Island! The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. The Large master bedroom has a King bed and bathroom with a walk-in shower with his/her sinks and a separate |
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2045 Gulf of Mexico Dr. #310 2045 Gulf of Mexico Dr. #310, Longboat Key, FL
Beach Condo Longboat Key area Island community
Seaplace is a wonderful, friendly community with lots of activities. This two bedroom, two bath condo is very nicely appointed and is equipped with everything you will need during your stay. There are two pools right on the ocean front, a large, relaxing clubhouse with WIFI. Stroll the beautiful sand on the beach for sunrise |
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1300 N Portofino Drive #S405 1300 N Portofino Drive #S405, Sarasota, FL
Condo Siesta Key area Island community
Owner will accept a short term 4 month + rental at 1950/month off-season and 3900/mo prime season (Dec-April) or a furnished annual rental at 2400/mo. Welcome to Siesta Harbor, a boating community on the Intracoastal Waterway for seniors 55 years of age and older. Fishermen and women can drop a line off the pier and |
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710 Treasure Boat Way 710 Treasure Boat Way, Sarasota, FL
Single Family Home Siesta Key area Island community
Easy bike ride or walk to Siesta Village. This well-kept home is perfect for outdoor entertaining by the pool. Open floor plan and large kitchen/family room. Enjoy Siesta Beach just minutes away. |
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800 Ben Franklin Drive #704 800 Ben Franklin Drive #704, Sarasota, FL
Beach Condo Lido Key / St. Armands Circle area Island community
Beautiful beach condo located on Lido Key at the Lido Ambassador. This turnkey furnished condo has one bedroom and one and a half bathrooms. Wood floors and tile throughout. The kitchen has stainless appliances. Master bedroom has a king sized bed, large walk in closet and soaker tub/shower combination. Guest bathroom has been updated with |
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500 S. Washington Drive #16A 500 S. Washington Drive #16A, Sarasota, FL
Condo Lido Key / St. Armands Circle area Island community
Cute and convenient condo located on the desired Lido Key. This first floor turnkey furnished condo has one bedroom, one bathroom and a remodeled kitchen with stainless steel appliances. Master bathroom has also been remodeled and has a stall shower. Heated community pool and hot tub for your enjoyment. Located just one block from Lido |
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1222 Center Place 1222 Center Place, Sarasota, FL
Single Family Home Lido Key / St. Armands Circle area Island community
Unique Mid-Century Modern home in renowned Lido Shores available for short term vacation rentals. Step into this meticulouosly updated home with all new furnishings and new decorating. The house features three bedrooms, the master has a king sized bed, the second bedroom has a queen sized bed and the third bedroom features six single beds |
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2910 Casey Key Road 2910 Casey Key Road, Nokomis, FL
Single Family Home Casey Key area Island community
Experience European elegance and sophistication at this stunning bayfront Casey Key residence, complete with deeded beach access. Idyllically sited along the gentle waters of Blackburn Bay and tucked along meandering mangroves, this residence designed by architect George Merlin showcases classic architectural design while maximizing waterfront vistas and privacy. The superb design is combined with masonry |
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1102 Ben Franklin Dr, #514 1102 Ben Franklin Dr. #514, Sarasota, FL
Beach Condo Lido Key / St. Armands Circle area Island community
Great location on Lido Beach, within walking distance of the Circle. This two bedroom, two bathroom condo has fabulous north beach views. One month minimum. Perfect Florida vacation property with a community pool/hot tub right on the beach. |
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1 Benjamin Franklin Drive PH3 1 Benjamin Franklin Drive PH3, Sarasota, FL
Condo Lido Key / St. Armands Circle area Island community
Absolutely gorgeous penthouse condo located in the desired community of St. Armand’s Tower North. Completely renovated, brand new professionally decorated unit, turnkey furnished and AVAILABLE for rent. Incredible Gulf and Bay views from the floor to ceiling windows greet you at every turn. The modern kitchen has lots of stone counter space and wood cabinets |
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3521 Casey Key Road 3521 Casey Key Road, Nokomis, FL
Beach House Casey Key area Island community
Gorgeous beach cottage and artist retreat, recently professionally decorated and ready for that perfect getaway. This house has a private 120 foot beach on pristine Casey Key. Step into this perfect house with walls of glass windows to give you endless gulf views and stunning sunsets. The living room has a decorative tiled fireplace, large |
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800 Benjamin Franklin Drive #202 800 Benjamin Franklin Drive #202, Sarasota, FL
Condo Lido Key / St. Armands Circle area Island community
Available now! 6 month minimum rental and turnkey furnished. 2/2 Absolutely gorgeous and updated floor to ceiling, this 2nd floor waterfront unit on Lido Key is just a few steps to the beach and crystal Gulf waters! Enjoy a sunset every evening in this beach front complex! You are 8/10 of a mile walking distance |
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1925 Gulf of Mexico Drive #309 1925 Gulf of Mexico Drive #309, Longboat Key, FL
Beach Condo Longboat Key area Island community
LONGBOAT KEY’S SEAPLACE Enjoy the tropical sea breezes and the Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Master Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and |