Longboat Key, FL Houses for Rent

Hurricane rebuild completed in 2025. Discover tranquility and comfort at our serene 3-bedroom, 2-bath home, nestled among lush tropical foliage on a peaceful corner lot in Longboat Key. Inside, experience a welcoming open floor plan with a brand-new living room, modern kitchen, and clean-cut updated bathrooms. Master bedroom features wet bar with mini fridge & windowed ensuite bath. The backyard

Keith Gordon GETMOREOFFERS

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 atmosphere.Step into

Andy Moore GULF COAST REALTY & MANAGEMENT

Merging classic elegance with modern luxury featuring high vaulted ceilings, a state-of-the-art kitchen, high-speed internet, and a cutting-edge reverse osmosis water system. Enjoy the convenience of an in-closet washer/dryer and UV air filtration for pristine air quality. Perfect for romantic getaways or peaceful solitude, with boat parking & public launch nearby. The property offers a furnished

Keith Gordon GETMOREOFFERS

Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private

Keith Gordon GETMOREOFFERS

Exceptional Rental Opportunity in Queens HarbourIntroducing a remarkable opportunity to rent a stunning 4-bedroom corner lot residence in the highly sought-after Queens Harbour community, located behind the gates of the Longboat Key Club. This property features a brand new roof and offers the perfect setting for those looking to embrace the Florida lifestyle.The home is filled with abundant

Danielle Gladding COLDWELL BANKER REALTY

Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood

Henry Rossi RENT SARASOTA

Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

Karie Gorgone WAGNER REALTY

Fabulous turnkey rental open for off-season. This European-styled home will surpass all your needs – whether you’re remodeling, relocating or simply need vacation time! Featuring three bedrooms, three ensuite baths, this 2-story home, boasts two lanai’s with seating, outdoor kitchen, a roof-top sun deck and sparkling heated lap pool. Upon entering the home, you’ll enjoy the bottom floor expanse

Diann Thelen GULF COAST RENTAL HOMES&CONDOS

Location, location, location. This furnished rental offers the perfect blend of convenience and waterfront living. Enjoy direct access to the Gulf of Mexico with a private dock and boat lift, take a walk on the pristine white sand beaches or relax and unwind in the pool. Nestled in a prime location just minutes from St. Armands Circle, you'll have access to the best dining, shopping and

Marcia Benson Berkshire Hathaway Florida Realty

Introducing a charming 3-bedroom, 2-bathroom single family home located in the prestigious Country Club Shores of Longboat Key, FL. This fully furnished property boasts deeded beach access, perfect for enjoying the sun and surf just steps away from your front door. The fenced backyard provides privacy and a great space for outdoor entertaining. Situated just 2.8 miles from the vibrant St. Armands

Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. 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 of walking trails, two heated pools,

Joseph Stephens ONE STEP AHEAD REALTY INC

Unique 3 bedrooms and 3 bathrooms property in Longboat Key ready for immediate occupancy, all repairs are done. Bay Isles community has a lot to offer to prospective long term renters. Set in The Bayou behind 2 security gates. House was remodeled in the last couple of years. Fully furnished with contemporary decoration and furniture. Kitchen equipped with high end stainless steel appliances and

Gary Dontsov LONDON FOSTER REALTY

BEACHFRONT JULY SPECIAL! $7,999 for the month. $2,000 discount! Available from 07-01-25 to 12-31-25, call for more details.Welcome to beachfront paradise on Longboat Key! This rare opportunity offers the best of coastal living with spectacular views of the coastline! Nestled along the shores of the Gulf of America, this three-bedroom, three-bathroom home invites you to enjoy the ultimate

Michael Cella CELLA'S REAL ESTATE INC

LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a

Teresa Ribaudo JENNETTE PROPERTIES INC

Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of

Jennifer LeBlanc PRECISE REALTY CORP

Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful décor

Jaime Barcelo GULF COAST REALTY & MANAGEMENT

Booked March through Sep 3rd 2025. Looking for a 3 month renter for January, February, and March or the month of January 2026. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floorplan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous

Jennifer LeBlanc PRECISE REALTY CORP

SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the

Diann Thelen GULF COAST RENTAL HOMES&CONDOS