Longboat Key Classified Ad Listings

2804 Avenue C. Annual rental. Unfurnished raised duplex 3BD/2BA island home just two blocks from the beach! Open floor plan, large bonus room that is perfect for a family/game room. Enjoy your morning coffee off of the master bedroom back deck or on the covered front porch. One car garage. Pets OK. Available August 1st. 2026.. 3 Bedrooms. 2 Bathroom. 1248 ft

1905 Tulip Dr. Welcome to the Siesta Stunner! This 1950s pool home has been completely remodeled down to the studs w/ designer finishes and furnishings and high ceilings throughout. A short walk or bike ride will get you onto Siesta Key and the house is walkable to both Publix and the Siesta Key Mall! The space is light and bright thanks to the 10ft ceilings, abundant windows and southern expos...

1001 Benjamin Franklin Dr Unit 507. LIDO TOWERS!!! Highly sought after FIFTH Floor 2 bedroom 2 bath condo in Lido Towers. Condo is newly renovated and updated. This beautiful condo overlooks the gulf of Mexico. Secure Building with Lido Beach Access. Enjoy the Beautiful Sunsets from the Sparkling Sandy Beach Across the Street. Lido Towers features a Heated Pool and Jacuzzi, BBQ on the Patio, Sa...

17939 WHEAT STACK COURT. Property for Rent in Parrish, FL for $2,650 with 4 bedrooms and 2 full baths. This 1,498 square foot property was built in 2026 on a lot size of 0.14.. Brand-new, never-lived-in designer living in gated Rye Crossing. Nestled on a quiet cul-de-sac, this 2026-built D.R. Horton "Freeport" layout delivers 4 bedrooms, 2 full baths, and a 2-car garage with an open, single-sto...

8105 Grand Estuary Trl Unit 204. BOOKED JAN/FEB/MAR 2026. AVAILABLE APRIL 2026. River Strand in Heritage Harbour, a beautiful, gated Golf and Country Club community. This nicely furnished 2-bedroom 2 bath condo has a screened balcony with golf course views, there is a Sleeper Sofa in the living area, 50 inch TV and DVD player, King bed in master with 40 inch flat screen TV, Twin Beds in 2nd bed...

6442 Colonial Dr. $4,000 (Jan-Apr), $2,500 (May-Dec), $3,000 year-round avg. Perfect for snowbirds or long-term! Spend your vacation in this charming 2-bedroom, 2-bath Gulf Gate home, ideally located just minutes from the sugar-white sands of world-famous Siesta Key. Thoughtfully furnished and designed for comfort, this 1,585 sq. ft. retreat has everything you need for a fun and relaxing getawa...

535 Forest Way. Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island's most sought-after communities-offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosph...

14226 Tree Swallow Way. Greenbrook Village single-family home for rent featuring 3 bedrooms, 2 full bathrooms, and a 2-car garage. This well-maintained home has tile flooring throughout, with laminate flooring in the primary bedroom. The eat-in kitchen provides a comfortable space for everyday dining, while the spacious primary bedroom features a large walk-in closet and a private full bathroom...

1104 WATERLINE COURT. Single Family Home for sale in Sarasota, FL for $950,000 with 3 bedrooms and 2 full baths. This 2,076 square foot home was built in 2023 on a lot size of 0.21.. Welcome to Lakehouse Cove at Waterside, where you can experience luxurious resort-style amenities, maintenance-free living and easy access to Lakewood Ranch, Waterside, UTC, downtown Sarasota and our area's most co...

1104 Yale Ave. Discover this spacious 4-bedroom, 2-bathroom pet-friendly home offering 1,861 sq. ft. of comfortable living space. The home's versatile layout accommodates a variety of needs, featuring ample room for relaxation and entertainment.. 4 Bedrooms. 2 Bathroom. 1861 ft

339 River Enclave Ct. RIVER STRAND Beautifully furnished 3 bedroom home with "bonus" room attached to master suite that is great office space. Great floor plan with living/dining and kitchen family room combo. Beautiful pool area overlooking lake, manicured property. Tenant pays $535 PLUS TAX fee for transfer of golf membership; amenities package includes not only golf, but tennis, fitness, res...

4799 Oak Forest Dr W Unit 43. Virtually Staged. Oak Forest is an updated community with mature trees and landscaping. The location is convenient to transportation, Siesta Key beaches, shopping, restaurants, social events, theatre and Downtown Sarasota. The community is impeccable maintained and updated. This villa has been updated and freshly painted with new carpet in the primary bedroom and l...

6440 Mourning Dove Dr Apt 402. Bayfront Living with Beautiful Water Views. Welcome to relaxed Florida living in this beautifully updated 2-bedroom, 2-bath Bayfront residence, located on the fourth floor of an elevator building. With direct views of the bay, this inviting home offers a wonderful combination of comfort, convenience, and scenery. From the moment you step inside, your eyes are draw...

3282 Tobero Ln. Welcome to this beautiful three-bedroom, two-bathroom home nestled in the heart of Sarasota County. This idyllic retreat offers a perfect blend of upscale interiors and a lush tropical backyard, promising an unforgettable getaway for families, friends, or couples seeking to enjoy the mild Floridian winter. The master suite boasts a king-sized bed and has direct access to the poo...

4509 30th Ln E. Welcome to this well-maintained 3 bedroom, 2 bath, 2 car garage rental home located in Bradenton, FL. This inviting residence offers a comfortable and functional floor plan with spacious living areas, a bright kitchen, and generously sized bedrooms. The primary suite features a private bathroom, while the additional bedrooms provide flexibility for family, guest, or a home offic...

*PRICE INCLUDES $10,000 FINANCE REBATE2027 Godfrey Sanpan 2500 SFLWTurn an ordinary day on the water into something extraordinary aboard the 2027 Godfrey Sanpan 2500 SFLW, available at Boater's World Bradenton! This sophisticated luxury tritoon redefines what it means to cruise in comfort, bringing together refined styling, innovative seating, and exciting performance capabilities in one remark...

4418 Useppa Dr. This home offers weekly rentals.Modern and comfortable furnishings with a very large open floor plan makes this vacation home ideal for entertaining.Modern and comfortable furnishings with a very large open floor plan makes this vacation home ideal for entertaining. You'll especially enjoy the fully equipped kitchen and lounge area, and separate game room. A quiet vacation home ...

51 Mac Ewen Dr Unit 1. ***AVAILABLE MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.. 1 Bedroom. 1 Bathroom. 623 ft

7205 Curtiss Ave Apt 2F. A charming two-bedroom condominium conveniently located near Siesta Key beach awaits you. Each bedroom boasts a comfortable queen-size bed for a restful night's sleep, complemented by TVs in both rooms for your entertainment. This unit features an indoor laundry room for added convenience, along with a screened-in lanai where you can unwind. Additionally, the eat-in kit...

5377 Crestlake Blvd Unit 69. Available for FEBRUARY AND MARCH 2027 Season! Enjoy this spacious 2-bedroom, 2-bath home with a garage overlooking a peaceful lake. This beautiful property features both a family room and a living room, along with the convenience of an in-unit washer and dryer. Perfectly located near Siesta Key, shopping, dining, and easy interstate access-everything you need is jus...