$8,000 per month
- 3 Beds
- 3 Baths
- 2,487 Sq Ft
- House for Rent
2377 Harbour Oaks Dr, Longboat Key, FL 34228
2377 Harbour Oaks Dr, Longboat Key, FL 34228$8,000 per month
2377 Harbour Oaks Dr, Longboat Key, FL 34228
2377 Harbour Oaks Dr, Longboat Key, FL 34228$10,000 per month
3111 Bayou Sound, Longboat Key, FL 34228
LOCATION, LOCATION, LOCATION. BEAUTIFUL TURNKEY FURNISHED SINGLE FAMILY HOME available in the sought after community of Bay Isles is available to rent. This lovely light, bright 3 bedroom plus 3 bathroom, two half bathroom home boasts 2,908 square feet, double primary bedrooms, living room/dining room combination, loft/den space and much much more. The home has been fully painted and newly
C. Alison Hunter JENNETTE PROPERTIES INC
$14,750 per month
513 Gunwale Ln, Longboat Key, FL 34228
Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation
Marcia Benson Berkshire Hathaway Florida Realty
$9,800 per month
640 Broadway St, Longboat Key, FL 34228
Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024
Christina Vescovo LPT REALTY, LLC
$14,400 per month
701 Broadway St, Longboat Key, FL 34228
Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances
Christina Vescovo LPT REALTY, LLC
$3,500 per month
573 Spanish Dr N, Longboat Key, FL 34228
NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL ($4,600/MONTH). LEASE -3 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.
Norma Mladineo COLDWELL BANKER REALTY
$25,000 per month
690 Old Compass Rd, Longboat Key, FL 34228
Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size
Teresa Ribaudo JENNETTE PROPERTIES INC
$19,975 per month
5801 Gulf of Mexico Dr, Longboat Key, FL 34228
Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows
Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT
$10,000 per month
614 Norton St, Longboat Key, FL 34228
Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle.Key Features:-Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the
Miranda Platt, PA RELAX REALTY GROUP INC
$14,500 per month
595 Bowsprit Ln, Longboat Key, FL 34228
Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this turn-key furnished 4-bedroom, 2.5-bath home in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station
Melissa Gissinger MICHAEL SAUNDERS & COMPANY
$6,500 per month
4780 Gulf of Mexico Dr, Longboat Key, FL 34228
BONUS FREE RENTAL DAYS! AVAILABLE 12/26/2025-1/31/2026 ONLY! Stay through New Years Eve for Free as a bonus. Fully Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2025! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets
Debby McCaig COLDWELL BANKER REALTY
$10,000 per month
2823 Gulf of Mexico Dr, Longboat Key, FL 34228
Available beginning June 1st, 2026. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of
Michael Cella CELLA'S REAL ESTATE INC
$11,500 per month
2254 Harbour Court Dr, Longboat Key, FL 34228
Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush
Alex Larchenko KELLER WILLIAMS ON THE WATER S
$11,000 per month
3390 Bayou Sound, Longboat Key, FL 34228
**This is a 2 month minimum vacation rental**Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this
Jennifer LeBlanc PRECISE REALTY CORP
$29,000 per month
591 Putting Green Ln, Longboat Key, FL 34228
LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin
Teresa Ribaudo JENNETTE PROPERTIES INC
$10,000 per month
825 Tarawitt Dr, Longboat Key, FL 34228
Welcome to your new Beach House Sanctuary!! Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot! Coveted lifestyle and location on a deep water canal in the heart of Longboat Key! This waterfront home has 125ft of seawall docking for a boat up to 30 ft. plus a jet ski lift and room for other water toys. Catch bait and start fishing in less than 30 minutes!
Ian Greenberg BRISTA REALTY LLC
$5,500 per month
957 Spanish Dr N, Longboat Key, FL 34228
AVAILABLE STARTING MAY 1, 2026. WITH 3 MONTH MINUMUM RENTAL. FULL WATERFRONT NEWLY RENOVATED (internal new photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main Yacht
Norma Mladineo COLDWELL BANKER REALTY
$10,000 per month
6979 Longboat Dr S, Longboat Key, FL 34228
Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room
Rinat Sikdar COLDWELL BANKER REALTY
$14,000 per month
830 Tarawitt Dr, Longboat Key, FL 34228
Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost 2500 Sq. Ft. of Interior Living, The Home Offers 4 Bedrooms, 3 Full Washrooms, 2 Balconies and
Ian Greenberg BRISTA REALTY LLC
$13,000 per month
613 Buttonwood Dr, Longboat Key, FL 34228
Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into
Jennifer LeBlanc PRECISE REALTY CORP
$6,900 per month
535 Forest Way, Longboat Key, FL 34228
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
Andy Moore GULF COAST REALTY & MANAGEMENT
$10,995 per month
2339 Harbour Oaks Dr, Longboat Key, FL 34228
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
$14,000 per month
531 Birdie Ln, Longboat Key, FL 34228
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
$11,250 per month
3210 Bayou Sound, Longboat Key, FL 34228
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
$8,000 per month
2369 Harbour Oaks Dr, Longboat Key, FL 34228
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
$11,550 per month
500 Schooner Ln, Longboat Key, FL 34228
Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through February 2027, Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. 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
Jennifer LeBlanc PRECISE REALTY CORP
$30,000 per month
6925 Longboat Dr S, Longboat Key, FL 34228
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 decor
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$13,000 per month
501 Channel Ln, Longboat Key, FL 34228
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 floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy
Jennifer LeBlanc PRECISE REALTY CORP
$12,500 per month
2319 Harbour Oaks Dr, Longboat Key, FL 34228
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