$7,000 Per Month
537 Outrigger Ln, Longboat Key, FL 34228
Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new
$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
$12,000 Per Month
2425 Gulf of Mexico Dr, Longboat Key, FL 34228
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath
$12,000 Per Month
714 Norton St, Longboat Key, FL 34228
Offered fully furnished and turnkey for lease terms from 6 to 12 months, this private Longboat Key canal-front retreat captures a dreamy beach lifestyle while blending original mid-century character with elevated coastal charm. The bright, open interior is thoughtfully furnished for comfort and entertaining, with ceiling fans throughout, a fully stocked kitchen and a brand-new appliance package.
Traci de Wid RESIDENTIAL WEALTH PARTNERS
$19,975 Per Month
5801 Gulf of Mexico Dr, Longboat Key, FL 34228
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 that bring in natural light and frame the Gulf.The
$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
$2,000 Per Month
3802 Gulf of Mexico Dr, Longboat Key, FL 34228
AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. $2000 PRICE LISTED IS FOR SEPTEMBER-DECEMBER ONLY. REACH OUT FOR SEASONAL RENTAL PRICE. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of
$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.
$8,900 Per Month
691 Russell St, Longboat Key, FL 34228
Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience.Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with
$14,500 Per Month
Unlisted Address
Pricing: In-Season: $14,500/month (60 Day Minimum) | Off-Season: $9,450/month | All rates include taxes and feesSunset at Banyan Bay is a beautifully appointed 2nd-floor Gulf-front condominium in the coveted Banyan Bay community on Longboat Key — one of Florida's most serene Gulf Coast barrier islands. This 3-bedroom, 3-bathroom residence sleeps up to 8 and offers sweeping views of the
Dave Holt PMI SOUTHWEST FLORIDA
$3,000 Per Month
820 Spanish Dr S, Longboat Key, FL 34228
Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active,
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
$4,000 Per Month
706 Spanish Dr S, Longboat Key, FL 34228
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
$10,000 Per Month
1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle
Jane Hunter JENNETTE PROPERTIES INC
$7,000 Per Month
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You
Andy Moore GULF COAST REALTY & MANAGEMENT
$11,900 Per Month
3210 Bayou Sound, Longboat Key, FL 34228
AVAILABLE HIGH-SEASON January - April, $11,900/month. LOW SEASON May - December, $7,000/month. 3 Month Minimum Stay. Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered TURNKEY furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms
Richard Ivan WAGNER REALTY
$5,800 Per Month
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$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
$10,500 Per Month
3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
Luxury Seasonal or Annual Rental in Grand Bay– Longboat KeyExperience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence
Desiree Doggett NEXTHOME EXCELLENCE
$10,500 Per Month
4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly
Norma Mladineo COLDWELL BANKER REALTY
$3,500 Per Month
2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural
Alex Larchenko KELLER WILLIAMS ON THE WATER S
$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
$4,500 Per Month
3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock, community kayaks, an electric kayak launch, and a fishing pier with a
Kathleen 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
$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
$4,200 Per Month
840 Bayport Way Unit 840, Longboat Key, FL 34228
This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The
Shirley Cuddy REALTY SERVICES INC
$5,500 Per Month
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through October 31, 2026! 60 Day Minimum Lease, not available Nov 1, 2026-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches
Scott Nold TNG PROPERTY MANAGEMENT
$11,000 Per Month
1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. 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. Relax on the lanai and take in the beautiful gulf views at sunset. The
Margaret Young JENNETTE PROPERTIES, INC.
$5,700 Per Month
3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
VACATION RENTAL!!! AVAILABLE JAN - MARCH 2027! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$4,700 Per Month
561 Tarawitt Dr, Longboat Key, FL 34228
Welcome to this beautiful waterfront property in Longboat Key, freshly renovated and ready for its next occupant. Upgrades include a hurricane-proof front door, fresh paint, and a kitchen with brand-new appliances. A washer and dryer are also included. Both bedrooms have their own bathrooms, and a bonus room off the living room with pocket doors could serve as a third bedroom or office. The
Edward Holloway INTEGRITY REAL ESTATE SERVICES LLC
$14,000 Per Month
1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$7,000 Per Month
1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$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
$12,000 Per Month
2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay.
Teresa Ribaudo JENNETTE PROPERTIES INC
$9,587 Per Month
4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of the
Gerald Cunningham KELLER WILLIAMS ON THE WATER S
$8,000 Per Month
1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
Prime location... This absolutely gorgeous fully furnished condo located in the Promenade Longboat Key with breathtaking water views from every room. It offers 2 bedroom/den/2 bathroom. The master bedroom features a king-size bed, elegant master bath separate bathtub, shower and a vidette for your convenience. For your guests the second bedroom offers 2 twin beds that can convert into a king-size
Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE
$15,000 Per Month
2823 Gulf of Mexico Dr, Longboat Key, FL 34228
AVAILABLE beginning November 1st. 6-month minimum lease. This availability won't last long. Call today and book your stay! 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
Michael Cella CELLA'S REAL ESTATE INC
$3,000 Per Month
3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
Steps from the Sand – Luxury Beach Condo with Pool Access!Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits!Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community
nicoletta buonaccordo ALTIS REALTY
$6,000 Per Month
Unlisted Address
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 primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST
Jane Hunter JENNETTE PROPERTIES INC
$13,000 Per Month
501 Channel Ln, Longboat Key, FL 34228
Booked all of July, September, Novemeber 2026, and all of 2027Experience elevated island living in this stunning coastal retreat featuring 4 bedrooms, 3 bathrooms, a private pool, and exceptional indoor-outdoor entertaining spaces.Designed with comfort and style in mind, the bright open-concept living area features soaring ceilings, designer finishes, and large sliding glass doors
Jennifer Le Blanc PRECISE REALTY CORP
$12,000 Per Month
2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
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