Location: Longboat Key , 34228
Do Not Show Listings
LONGBOAT KEY, FL 34228
$6,0001121 Days on yellowkey MLS ID: A4572396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1977Community: Seaplace IiiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 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 ARMANDS CIRCLE of restaurants, shops and entertainment.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Jane Hunter (941-896-0622)
730 FOX ST, LONGBOAT KEY, FL 34228
$5,500156 Days on yellowkey MLS ID: A4679347
REDUCED by $1,000 (15.4%) on 05/25/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1350 Built: 1965Community: Longbeach On Longboat KeySingle Family
Remarks: 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 with dining are and spacious kitchen will make you feel at home right away. The kitchen is fully equipped for your convenience. Outdoors of this home is even more welcoming and paradise-life. Lush and tropical garden around the beautiful swimming pool, cabana with comfortable seating or other seating areas are there just for our guests. There is plentiful parking spaces in front of the house or next to it. And - the beaches..yes that is what matters. Whitney Beach on Longboat Key, couple minutes of walk. Or you can visit the Beer Can Island, popular place for boats to hang out. Coquina Beach on Anna Maria Island is not far also. La Paloma just has it all! Sweet home with good vibe close to all you need on vacation!
Listing is courtesy of: ENVISION REALTY PARTNERS LLC (941-840-3188)
Listing Agent: Linda Votrubova (941-840-3188)
603 LONGBOAT CLUB RD #204N, LONGBOAT KEY, FL 34228
$12,00098 Days on yellowkey MLS ID: A4686763
0 Days Off yellowkey (back on 5/23/2026)
REDUCED by $3,000 (20.0%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1560 Built: 1970Community: Longboat Key TowersSpa: YesCondo
Remarks: LONGBOAT KEY CLUB – GULF FRONT LUXURY RENTAL Enter the private, gated community of Longboat Key Club and experience true coastal paradise with breathtaking Gulf-front views. This completely remodeled 2-bedroom, 2-bath condominium showcases elegant, high-end finishes throughout. The bright and open living area features stunning marble flooring and walls, with expansive windows and a large private balcony that perfectly frame the panoramic ocean views. The modern kitchen has been thoughtfully redesigned with a sleek style, offering a large island and seamless flow into the living and dining areas—ideal for entertaining. The dining room also enjoys beautiful water views, creating the perfect backdrop for every meal. The spacious primary suite is a private retreat, while the luxurious primary bathroom makes a bold statement with striking marble finishes. The second bedroom is generously sized and comfortably accommodates double beds. Residents enjoy resort-style amenities including a heated beachfront pool and spa, a state-of-the-art fitness center, sauna, steam room, and 24-hour security. Available for 3- to 6-month stays.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)
Listing Agent: Lily Behrends (941-526-9121)
4825 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$7,800421 Days on yellowkey MLS ID: A4651021
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Community: Westchester Condo Apts Un 3Condo
Remarks: SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers a Queen and 1 twin bed with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. BOOKED JAN-MAR, 2027.
Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)
Listing Agent: Diann Thelen (941-920-0758)
6979 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$10,000333 Days on yellowkey MLS ID: A4660175
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1454 Built: 1974Community: Longbeach On Longboat KeySingle Family
Remarks: 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 includes bunk beds for family fun. Accommodating up to 9 guests, the property is just a short stroll to pristine Whitney Beach and nearby fishing docks, with top local restaurants and cafes — like Mar Vista, Shore, Whitney’s, and more — only minutes away. A local owner ensures attentive service to make your stay unforgettable. $10,000 off season/$14,000 season.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
1050 LONGBOAT CLUB RD #803, LONGBOAT KEY, FL 34228
$6,00038 Days on yellowkey MLS ID: L4961980
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974Community: Privateer NorthSpa: YesCondo
Remarks: AVAILABLE 9/1/2026 to 12/31/2026. Oceanfront 2 bed/2 bath luxury condo on the 8th floor with beach and golf course views, two private balconies, and resort-style amenities just steps from the sand.The open-concept living and dining area features a custom bar and stylish decor, creating an inviting space to relax or entertain. A dedicated office makes working remotely effortless, while the sleek bar with wine refrigerator is perfect for evening cocktails at home. The fully equipped kitchen with built-in pantry offers everything you need, and the two serene bedrooms with King beds each enjoy convenient access to a full bath.This private, gated resort community offers a true coastal club experience. Host gatherings in the large community room, then move outdoors to the oceanfront pool, jacuzzi, fire pit, and grilling patio. Stay active with a swimming pool, workout room, pickleball, and shuffleboard courts on-site, then stroll directly onto the beach for a swim or sunset walk along the shoreline. 3 MONTH MINIMUM. Rental includes all furniture, appliances, dishes, cookware, and linens. Covered Parking spot #10 included with additional guest parking, seperate storage area for beach/pool items.
Listing is courtesy of: XCELLENCE (866-595-6025)
Listing Agent: Melissa Kontny (863-529-7465)
909 SPANISH DR N, LONGBOAT KEY, FL 34228
$2,95036 Days on yellowkey MLS ID: A4694346
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1300 Built: 1969Community: Spanish Main Yacht ClubSpa: NoVilla
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven, slow-close drawers, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with frameless glass shower and double sinks, plus a large walk-in closet. Step through new double doors to a generous screened lanai overlooking lush wetlands and Bay views, perfect for relaxing, dining, or using as a flexible third space, complete with retractable awning, brick paver patio, hurricane-rated windows and doors, motion lights, and electric blinds. In the vibrant 55+ Spanish Main Yacht Club community enjoy a pool, shuffleboard, private deeded beach access on Longboat Key, and easy boating, fishing, and cycling, all just minutes from St. Armands Circle, downtown Sarasota, dining, shopping, and the airport. Basic cable and water included. Move-in ready and waiting—call for details on this piece of paradise.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Alex Lane (941-960-3080)
601 LONGBOAT CLUB RD #902S, LONGBOAT KEY, FL 34228
$9,000198 Days on yellowkey MLS ID: A4674604
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1970Community: Longboat Key TowersSpa: YesCondo
Remarks: Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2027. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course from the bedrooms, while evenings wind down with glowing sunsets over the Gulf from the main living spaces. The primary suite offers walk-in closets and a peaceful retreat, and the open layout creates an effortless flow for entertaining or quiet nights at home. Residents enjoy resort-style amenities including a heated beachfront pool and spa, fitness center, sauna, steam room, and around the clock gated security. Water, cable, Wi Fi, and parking are included, making your stay truly effortless. Located within the Longboat Key Club community, Longboat Key Towers offers a serene beachfront escape while keeping you just minutes from the dining, culture, and lifestyle that make Sarasota so special.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Irma Scherer (941-279-3630)
2319 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$12,5003722 Days on yellowkey MLS ID: A4151865
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2532 Built: 1986 Tax: $8,895 (2021)Community: Harbour OaksSingle Family
Taxes:$8,895
Tax Year: 2021
Remarks: 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 perfect Winter getaway. One visit to this 3BD+Den/2.5BA golf course detached home will have you wanting more! It has been updated in all the newest tones, is fresh, and combined with natural lighting, is so inviting. Pavered drive and lush landscaping and walkway lead you into the foyer entry. The combined living/ dining area is warm and inviting with vaulted ceilings, tile flooring and new comfortable furnishings. The kitchen is designed for entertaining or just relaxing with a marvelous view of the 2nd green. The den is a cozy retreat for TV or for catching up on work or emails in the dinette area. The private and spacious master suite offers ensuite bath and has a seating area to relax and enjoy the views! The second bedroom features queen accommodations and the third bedroom offers twins. All have their own private entrance for a relaxing stay. Additional charges for pool heater use. This marvelous turnkey residence comes complete with gated security, Wifi, inside laundry, 2 car garage, private and community pool and easy access to shopping, dining and cultural arts from St. Armands Circle to downtown Sarasota. Booked Jan - April 2027.
1050 LONGBOAT CLUB RD #1006, LONGBOAT KEY, FL 34228
$6,0001320 Days on yellowkey MLS ID: A4552081
Remarks: Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of the gulf. Gorgeous custom kitchen. Granite counters, beautiful muted gray plank flooring. Turnkey furnished with newer linens and a brand new hurricane door off kitchen and dining to master bedroom balcony. Just bring your toothbrush and clothes. Desired location and direct front penthouse sitting right on the Gulf of Mexico w Private beach and chairs and umbrellas for quit time on your beach. The two balconies bring the water to you so you can enjoy a breathtaking sunsets and the unobstructed views everyday. The enormous heated pool and spa, and tennis courts, clubhouse and fitness center. Onsite management from 9 to 4 Monday through Friday. Go over Longboat Key Bridge and take a turn at first stoplight into LONGBOAT KEY RESORT GOLF AND TENNIS CLUB, TELL GATE GAURD AND SAY SHOWING PRIVATEER NORTH AND GO DIRECT TO BUILDING. This complex PRIVATEER NORTH is located furthest South to St. Armand's S0 YOU ARE NOT IN A LOT OF TRAFFIC and minutes to St. Armand's and the mainland.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
1050 LONGBOAT CLUB RD #804, LONGBOAT KEY, FL 34228
$5,0001158 Days on yellowkey MLS ID: A4567693
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Community: Privateer NorthSpa: YesCondo
Remarks: AVAILABLE OFF SEASON AND SEASONAL. RENTAL MAY 1, 2026 THROUGH November 30, 2026 AT $5000 A MONTH AND SEASONAL JANUARY 1, 2027 THROUGH APRIL 30, 2027 for $7500. Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor residence. Views from all windows and from the outdoor patio a great view of of the Gulf. Split bedroom plan for privacy. Master bedroom with a king size bed, walk in closet and the all tile bathroom has a convenient walk in shower. 2nd bedroom has a queen comfortable pull out sofa and built in desk area and bathroom tub and shower combination. Large open living area completely tiled with dining table and enjoy all the best of the galley kitchen for easy entertaining. The amenities will complete your time in Paradise in Florida. New clubhouse room with full kitchen. Enormous heated swimming pool and spa, fitness center, sauna, tennis courts, bike storage, pickle ball and have dinner on the beach with outdoor grill area. Restaurants are everywhere along with only minutes to Famous ST. Armand's Circle for great shopping and more of top notch Restaurants. . Walk the 9 mile Beach or ride your bike on Special Longboat Key. Includes internet, electric and cable and more. Turn key furnished. Just pack your bags. Won't last long.
2301 GULF OF MEXICO DR #102N, LONGBOAT KEY, FL 34228
$16,00056 Days on yellowkey MLS ID: A4692071
INCREASED by $7,000 (77.8%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatSpa: YesCondo
Remarks: Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with stainless steel appliances, and a bright, open living and dining area that flows seamlessly onto a private balcony—perfect for morning coffee while watching dolphins play or enjoying spectacular sunsets. The primary bedroom boasts an en-suite bath, while the guest bedroom provides comfort and privacy. Both bedrooms, along with the living room, deliver direct, unobstructed ocean views. This residence comes fully furnished. Additional features include impact-resistant windows and doors, covered parking, and access to the Islander Club’s exceptional amenities: a 24-hour fitness center with Har-Tru tennis courts, an oversized beachfront swimming pool, billiards, a library, and a vibrant community atmosphere just steps from the sugar-sand beach. Located in the heart of Longboat Key on St. Armands Circle and downtown Sarasota, this property offers the perfect blend of coastal luxury and relaxed island living. Whether you're seeking a seasonal rental or a long-term retreat, this oceanfront gem is move-in ready and delivers the best of island living with direct beach access and unforgettable Gulf vistas.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Michele Conn (612-414-7052)
4780 GULF OF MEXICO DR. VILLA 5, LONGBOAT KEY, FL 34228
$7,000252 Days on yellowkey MLS ID: A4668115
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1974Community: Windward Bay AmdVilla
Remarks: 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. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$6,00041 Days on yellowkey MLS ID: A4693849
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatCondo
Elementary School: Southside Elementary
High School: Riverview High
Middle School: Booker Middle
Remarks: Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community. Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary suite includes an ensuite bath and walk-in closet, while the guest bedroom offers comfort and privacy for visitors. Residents at THE ISLANDER on LONGBOAT KEY enjoy direct BEACHFRONT access along with resort-style amenities including a private beach, heated pool, fitness center, sauna, tennis, pickleball, and on-site management. Offered at $6,000/month May through December and $10,000/month January through April. AVAILABLE NOW for immediate occupancy. Contact listing agent for showing requests. OPEN FOR 2027 SEASON RESERVATIONS - 3 MONTH MINIMUM
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Richard Ivan (941-800-8891)
1581 GULF OF MEXICO DR #307, LONGBOAT KEY, FL 34228
$15,000229 Days on yellowkey MLS ID: A4671506
REDUCED by $5,000 (25.0%) on 05/15/2026
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1721 Built: 2024Community: St. RegisCondo
Remarks: Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully designed interiors featuring soaring ceilings and expansive floor-to-ceiling sliding glass doors that wrap around the living, dining, and kitchen spaces — framing breathtaking sunrise and sunset views. The gourmet kitchen is a chef’s dream, appointed with Wolf and Sub-Zero appliances, including a six-burner gas cooktop, double ovens, and a paneled side-by-side refrigerator and freezer. The elegant owner’s suite offers a private sanctuary with a spacious walk-in closet featuring custom wardrobe cabinetry, a frameless walk-in shower, and a secluded water closet. A private elevator with keyless entry provides direct access from your private two-car garage into your residence for ultimate convenience and privacy. Nestled within 17 acres of pristine beachfront, The Residences are part of Sarasota’s most exclusive resort enclave. Enjoy unparalleled amenities, including access to St. Regis Butler and Concierge services, a residents-only pool and spa, a private clubhouse, a state-of-the-art fitness center, and beachside cabanas. Just steps away, immerse yourself in the world-class offerings of The St. Regis Longboat Key Resort — from the pristine private beach and family-friendly pools to the unique saltwater lagoon wildlife experience, home to resident Aldabra tortoises. Indulge in rejuvenation at the oceanfront spa featuring vitality pools or delight in one of the resort’s vibrant, chef-driven dining destinations. Experience coastal luxury redefined — The Residences at The St. Regis Longboat Key invite you to live where timeless elegance meets the serenity of the sea.
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)
Listing Agent: Jaime Barcelo (941-275-3233)
1591 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228
$15,00064 Days on yellowkey MLS ID: A4691168
REDUCED by $2,000 (11.8%) on 05/15/2026
Bed: 1 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1556 Built: 2025Community: St. Regis Longboat KeyCondo
Remarks: Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous outdoor terrace—ideal for entertaining or simply enjoying the serene waterfront setting. Inside, the chef-inspired kitchen showcases sleek Poggenpohl cabinetry and a full suite of premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, full-size refrigerator, and beverage center. Designed with timeless elegance, the interiors feature curated earth-tone finishes by Marc-Michaels Interior Design. The luxurious owner’s suite offers direct terrace access—perfect for morning coffee with a view—along with a spa-inspired bath complete with dual vanities, soaking tub, oversized glass-enclosed shower, and a Toto bidet water closet. The thoughtfully modified floor plan includes two full bathrooms and comfortably accommodates guests. Set within the exclusive Residences at The St. Regis, this property offers access to over 17 acres of meticulously maintained grounds and 800 feet of pristine Gulf-front shoreline. Residents enjoy an unmatched lifestyle with access to world-class amenities, including personalized butler and concierge services, a renowned spa, in-residence dining, and private resident-only offerings such as a clubhouse, fitness center, pool, spa, and dedicated beach area. Don't miss this rare opportunity to live where others vacation.
914 SPANISH DR S #76, LONGBOAT KEY, FL 34228
$6,50084 Days on yellowkey MLS ID: A4687894
REDUCED by $250 (3.7%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1341 Built: 1968Community: Spanish Main Yacht Club CondoCondo
Remarks: 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 bayfront sunrises, with Gulf-side sunsets just a short stroll away. Thoughtfully designed and tastefully furnished, the home offers high-end mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. Residents enjoy access to a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, shuffleboard courts, and wonderful neighbors. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a short drive to Anna Maria Island, this property offers the perfect blend of tranquility and accessibility. Whether you're boating, fishing, or simply relaxing in the bright Florida room, this is a rare opportunity to experience the Longboat Key lifestyle at its finest. Seasonal rental rates are $6,750/ month in-season and $3950/ month off-season. One tenant must be age 55 or older in accordance with community requirements. Apply now!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
3060 GRAND BAY BLVD #172, LONGBOAT KEY, FL 34228
$7,85045 Days on yellowkey MLS ID: A4690978
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2250 Built: 1994Community: Grand Bay 1Spa: YesCondo
Remarks: LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major updating, with all new designer furniture and furnishings, new custom kitchen and bathrooms. Floor to ceiling glass with panoramic views from every room in the house. MOVE-In and enjoy the Luxury lifestyle and amenities that abound at Grand Bay. GRAND BAY is a 24-hour-manned, GATED community where residents can enjoy two heated swimming pools, hot tub spa, fitness center, tennis, private garage, large clubhouse, many on site activities. Residents can enjoy the Bay Isles Beach Club private beach access to the world famous beach on the Gulf of Mexico. Close to St. Armand's Circle, Downtown Sarasota, and Ana Maria Island. OPEN FOR RESERVATION May through December 2026 for a THREE MONTH or longer stay. There is a 30 day tenant application process with the Grand Bay COA. NO PETS/No Smoking. Additional charges 13% sales/resort tax to be paid by tenants. May through November $7,850. Reservation Confirmed for February through March 2027.
Listing Agent: Patrice Ivan (941-993-0823)
3802 GULF OF MEXICO DR #A204, LONGBOAT KEY, FL 34228
$2,50063 Days on yellowkey MLS ID: A4691384
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 761 Built: 1970Community: Beach Harbor ClubCondo
Remarks: AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. 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 comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright and inviting floor plan featuring a well-equipped kitchen, spacious living area, and a private bedroom suite designed for relaxation. The unit includes the added convenience of an in-unit washer and dryer, making extended stays effortless. Enjoy your morning coffee or evening unwind with a Gulf view, while being just moments from the community’s private beach access—only a short walk across Gulf of Mexico Drive. Beach Harbor Club offers resort-style amenities including: Large heated community pool Fitness center Clubhouse for social gatherings Marina and bayfront dock access Community grills and outdoor seating areas Covered parking and bike storage Located in the heart of Longboat Key, you are minutes from Publix, CVS, St. Armands Circle, downtown Sarasota, and Anna Maria Island, giving you easy access to dining, shopping, and entertainment while still enjoying a peaceful beachside setting. Non-smoking unit No pets allowed. Sate and local tourism tax applies to any lease 6 months or less, along with application fees, and $250 cleaning fee.**
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Brigette Marcus (941-315-9500)
2425 GULF OF MEXICO DR #11F, LONGBOAT KEY, FL 34228
$12,000296 Days on yellowkey MLS ID: A4663629
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973Community: Sea Gate ClubCondo
Remarks: 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. Tastefully decorated with flowing neutral tones. This corner unit offers views from every room with Floor-To-Ceiling windows and remote control window treatments. There are many amenities in this beautifully maintained building. They include Climate Controlled Bicycle Room and Kayak Storage, Gulf Front Heated Pool, Har-Tru Tennis Courts, Fitness Room, Social Room and Conference Room all for your use. Walking distance to Publix Market and minutes to St Armand's Circle and Downtown Sarasota for boutique shopping, Fine and Casual Dining and our renowned Theater District. Don't hesitate to make this your next vacation spot. This property is available beginning 12/04/2025. Building requires a 2 months minimum rental. LUXURY VACATION RENTAL, LONGBOAT KEY, GULF OF MEXICO, SARASOTA VACATION RENTAL.
Listing Agent: Teresa Ribaudo (941-376-4500)
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