$5,000 Per Month
- 3 Beds
- 2 Baths
- 1,635 Sq Ft
- Condo for Rent
5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228$5,000 Per Month
5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228$12,500 Per Month
615 Dream Island Rd Unit 107, Longboat Key, FL 34228
Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip
Jerome Henin HENIN REALTY
$12,000 Per Month
Unlisted Address
Enjoy resort-style living on prestigious Longboat Key in this completely updated and renovated 3-bedroom, 2.5-bathroom villa. Located in Harbour Circle, an enclave of 42 villas in the guard-gated, maintenance-free, community of Bay Isles, this 2,396 SF open floorplan has soaring ceilings and an abundance of natural light through the new high-impact doors and windows that uplifts and illuminates.
Teresa Ribaudo JENNETTE PROPERTIES INC
$6,500 Per Month
914 Spanish Dr S Unit 76, Longboat Key, FL 34228
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
$4,800 Per Month
616 Lyons Ln, Longboat Key, FL 34228
Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a
Steve Barthelemy ROOST REALTY INC.
$4,750 Per Month
1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights*Direct
Donna Channey WAGNER REALTY
$2,800 Per Month
1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis,
Annabelle Newland STOCKTON REALTY ADVISORS LLC
$24,750 Per Month
1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
Offered at $24,750 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach
Carol Aviles MICHAEL SAUNDERS & COMPANY
$2,500 Per Month
3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
2 bed, 2 bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with
Dakota Magnus FLORIDA GALLERY REAL ESTATE
$4,000 Per Month
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.
Janette Schafer COLDWELL BANKER REALTY
$2,500 Per Month
3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
1-bed, 1-bath seasonal or annual rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community
Dakota Magnus FLORIDA GALLERY REAL ESTATE
$3,200 Per Month
747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
GORGEOUS BAY VIEWS. Located in a quiet association of only eight units. Annual Unfurnished unit; open kitchen/living and dining area with master bedroom and tub/shower combo in en-suite bath. Canal views with private dock and boat lift (a boater and fisherman's dream). Drop a line outside your back door! Screened lanai with washer/dryer. Exterior parking immediately outside the unit with gas BBQ
Gregory Koss WAGNER REALTY
$3,600 Per Month
420 Firehouse Ct Unit 10, Longboat Key, FL 34228
Seldom available annual rental on the coveted north end of Longboat Key. This beautifully remodeled 2-bedroom, 2-bath condo boasts new appliances, cabinets, flooring, and modern fixtures throughout. Both bedrooms feature spacious walk-in closets, and a separate utility room includes washer and dryer hookups. Embrace the laid-back coastal lifestyle with quick access to beaches, restaurants,
Gregory Koss WAGNER REALTY
$4,500 Per Month
600 Russell St, Longboat Key, FL 34228
Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room
Gregory Koss WAGNER REALTY
$5,500 Per Month
730 Fox St, Longboat Key, FL 34228
Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room
Linda Votrubova ENVISION REALTY PARTNERS LLC
$35,000 Per Month
7147 La Lenaire Dr, Longboat Key, FL 34228
A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian
Chase Moore SIGHT REAL ESTATE, LLC
$40,000 Per Month
1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$2,500 Per Month
3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
1-bed, 1-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on
Dakota Magnus FLORIDA GALLERY REAL ESTATE
$9,000 Per Month
601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228$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
$7,500 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
$8,650 Per Month
701 Broadway St, Longboat Key, FL 34228
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 and a gas range. The private, fully fenced backyard offers a lagoon style heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing sound of swaying palms. Completely
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 Jan - April ($5,500/MONTH). 6 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
$10,000 Per Month
1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with
Brad Wilson M&M PROPERTY MANAGEMENT GROUP
$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
$9,000 Per Month
829 Bayport Way Unit 829 B, Longboat Key, FL 34228
829 Bayport Way Unit 829 B, Longboat Key, FL 34228$7,000 Per Month
4780 Gulf of Mexico Dr, Longboat Key, FL 34228
Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access.
Debby McCaig COLDWELL BANKER REALTY
$10,500 Per Month
615 Dream Island Place Unit 201, Longboat Key, FL 34228
615 Dream Island Place Unit 201, Longboat Key, FL 34228$7,100 Per Month
3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai
Brenda Cozy COLDWELL BANKER REALTY
$7,750 Per Month
5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228$13,000 Per Month
806 Bayport Way Unit 806, Longboat Key, FL 34228
806 Bayport Way Unit 806, Longboat Key, FL 34228$13,000 Per Month
609 Bayport Way Unit 609, Longboat Key, FL 34228
609 Bayport Way Unit 609, Longboat Key, FL 34228$11,300 Per Month
2823 Gulf of Mexico Dr, Longboat Key, FL 34228
July 2026 is currently available! Call today! 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 single family home invites you to experience the ultimate beachfront lifestyle. Relax under the sun,
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
$10,000 Per Month
1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
Available for 2027 Season. Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each offering a
Jenna Genovese KELLER WILLIAMS ON THE WATER S
$11,000 Per Month
3390 Bayou Sound, Longboat Key, FL 34228
**Two-Month Minimum Rental** Escape to paradise at this beautifully updated Bay Isles retreat on Longboat Key. Nestled among lush tropical landscaping and majestic oak trees, this private island getaway offers the perfect blend of luxury, comfort, and relaxation. Located within the exclusive gated community of Bay Isles, guests enjoy easy access to Longboat Key's world-renowned beaches, marinas,
Jennifer Le Blanc PRECISE REALTY CORP
$2,500 Per Month
3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush
Teresa Ribaudo JENNETTE PROPERTIES INC
$7,000 Per Month
737 Bayport Way Unit D, Longboat Key, FL 34228
737 Bayport Way Unit D, Longboat Key, FL 34228$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
$4,900 Per Month
4420 Exeter Dr Unit 208, Longboat Key, FL 34228
Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so
Armando Gonzalez AG REALTY SERVICES LLC
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