Longboat Key Homes with Pool

Longboat Key Homes with Pool

Welcome to Longboat Key, Florida, a serene paradise nestled along the Gulf of Mexico. Known for its stunning white-sand beaches and vibrant sunsets, Longboat Key is the epitome of coastal living. This upscale barrier island offers a unique blend of luxury and tranquility, making it a coveted destination for those seeking a peaceful retreat or a permanent residence.

Longboat Key boasts an array of charming neighborhoods, each with its own distinct character. From waterfront estates to cozy beach cottages, the real estate options are as diverse as the residents who call this island home. A highlight of many properties here is the presence of private pools, providing residents with the perfect oasis to unwind and soak up the Florida sunshine. Imagine stepping out of your beautifully designed home to dive into your crystal-clear pool, surrounded by lush tropical landscaping—it's the ultimate Florida lifestyle.

In addition to its stunning homes, Longboat Key offers an array of recreational activities. The island is renowned for its world-class golf courses, tennis clubs, and pristine parks. Nature enthusiasts can explore the Longboat Key Nature Park, while food lovers can indulge in the exquisite dining options that line the coast. With a vibrant community spirit and a plethora of events throughout the year, Longboat Key is not just a place to live; it's a lifestyle.

If you’re looking for a home with a pool in this idyllic setting, you’ll find a range of options that cater to your every desire. Let Longboat Key be your next destination, where luxury meets laid-back island living!

Newest Longboat Key Homes with Pool

$624,900
2 Beds ⋅ 3 Baths ⋅ A4706809 MLS ⋅ Fairway Bay 1 BLDG.
Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

1920 Harbourside Drive Unit 1003, Longboat Key
$4,699,999
5 Beds ⋅ 5 Baths ⋅ A4707025 MLS
Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities. Designed for effortless coastal living, this sophisticated home combines coastal contemporary architecture, elevated construction above current flood requirements, an oversized homesite, and beautifully curated tropical gardens creating a private, resort-like setting. Inside, exceptional craftsmanship is evident throughout. The chef’s kitchen features a waterfall quartzite island, brass-strapped custom hood, panel-front refrigeration with fridge, freezer, and wine tower, vaulted beamed ceiling with concealed cove lighting and Thermador appliances. Designed to be a true masterpiece sure to impress. The great room showcases a walnut-clad fireplace wall, custom built-ins, wide-plank engineered wood floors, backlit tray ceiling, and expansive sliding glass doors opening to the outdoor living areas. The primary suite overlooking the tranquil back yard, offers a spa-inspired bath with freestanding soaking tub, rain shower, dual vanity, and customized walk-in closets. This floor plan also allows for an additional first floor primary or guest bedroom suite with custom full bath. The second floor offers three additional bedroom suites providing beautifully appointed accommodations for family and guests. Outdoors, the home becomes its own private resort. A covered lanai opens to a heated saltwater pool and spa, beautifully landscaped backyard with its own private putting green, and stainless-steel outdoor kitchen with built-in gas grill—an exceptional setting for entertaining, relaxing, or perfecting your short game at home. The location completes the experience. Set in south Longboat Key, the home is within walking distance of the Longboat Key Club, with golf, tennis, marina, dining, and beach club amenities nearby. Bay Isles residents also enjoy access to their own private Gulf-front Beach Club with powder-soft sand and spectacular Gulf waters. The Beach Club also provides bbq grills, pavilion, locker rooms, storage, and ice machine. New construction, exceptional design and quality, private beach access, and one of Longboat Key’s premier locations—this home offers a rare opportunity to enjoy the Bay Isles lifestyle from day one. Close to Sarasota International Airport, downtown dining and entertainment, and everything wonderful offered by the beloved St Armands Circle.

3360 Bayou Sound, Longboat Key
$1,549,000
3 Beds ⋅ 3 Baths ⋅ A4707000 MLS
Discover the ease and enjoyment of waterfront living on the north end of Longboat Key. This spacious canal home offers flowing indoor and outdoor spaces, fabulous boating, convenient neighborhood beach access, private heated pool, and so much more. At the front entry you are greeted by double doors opening to a generous foyer and an inviting, open floor plan with high ceilings. A welcoming and spacious great room provides gorgeous tropical views, plenty of room for relaxing or entertaining, and features a custom fireplace. The updated center-island kitchen features quartz countertops, generous workspaces, a wine cooler, stainless-steel appliances, and separate pantry, creating a welcoming place to cook and gather. Updates throughout including baths, flooring, and integrated fire protection add to the home’s appeal, while a large utility room with washer and dryer provides practical workspace. The flexible layout offers two split bedrooms plus a den that can serve as a third bedroom, along with three baths. The large primary features a walk-in closet, en-suite bath with soaking tub and custom walk-in shower, and opens to the outdoor covered lanai with its water views. The guest suite – split from the primary – offers an adjoining full bath, assuring privacy for visiting family and friends. On the main level an expansive covered lanai provides plenty of space for seating and dining and boasts water views from every angle, offering a comfortable setting for quiet mornings or evening gatherings. On the home’s lower-level, you’ll discover two bonus areas easily reimagined as a game room, media room, exercise room, or comfy lounging area. There is also a private office-den that could easily be converted to additional guest space. The newly refinished 30x15 pool enjoys an oversize deck, covered areas, outdoor shower, and new pool heater and equipment. With 80’ of canal frontage there is plenty of room for your boat, kayaks, paddleboards, and all your water toys. The three-car garage provides plenty of storage for cars, golf cart, beach equipment, and more. Longboat’s north end location is also home to a multitude of water-front dining options including The Shore, Mar Vista, Ventura’s, and Longbeach Café along with easy access to shops, groceries, Anna Maria, St Armands, Sarasota, and so much more. An idyllic lifestyle awaits: launch a day of boating, venture the nearby waterways by kayak or paddleboard, take a short walk to the beach, lounge poolside, or enjoy whatever your pleasure with so much to do and explore. Easy to maintain, plenty of room to entertain, and peaceful to return to, this home brings together the best of the Longboat Key lifestyle.

783 Marbury Lane, Longboat Key
$2,695,000
3 Beds ⋅ 4 Baths ⋅ A4705030 MLS
Waterfront living takes center stage at this impressive Queens Harbour residence, where more than 3,000 square feet of indoor living open to a tropical pool and spa, covered outdoor living, and a private dock with boat lift on a navigable canal with convenient access to Sarasota Bay. Set behind the gates of Bay Isles, the home offers generous living spaces and an exceptional Longboat Key lifestyle. A paver drive framed by mature tropical landscaping leads to the striking two-story entrance and double glass doors. Inside, soaring tray ceilings, plantation shutters, architectural details and abundant glass create a bright, open feel. A private office sits just off the foyer before the floor plan opens to the main living areas. The great room features a dedicated bar and flows into adjoining living spaces, with sliders opening to the covered lanai, summer kitchen and pool. The kitchen offers abundant white cabinetry, contrasting stone countertops, a large center island with second sink and paneled refrigerator. A light-filled dining area opens directly to the outdoor living space. The first-floor primary suite overlooks the pool and features an aquarium-glass sitting area, tray ceiling, spacious walk-in closet and bath with split vanities, spa tub and glass-enclosed shower. A second en suite bedroom completes the main level. Upstairs, a generous guest suite can serve as a second primary retreat with a walk-in closet and updated en suite bath. Outside, the pool and spa with cascading waterfall are surrounded by paver decking and tropical landscaping. The covered lanai and summer kitchen create an inviting entertaining space, while the private dock and boat lift provide direct canal access to Sarasota Bay. Ownership in Bay Isles includes membership in the private Gulf-front Bay Isles Beach Club, offering residents direct beach access, covered gathering areas, picnic and barbecue facilities and other conveniences for enjoying the Gulf. Separate optional membership to the Longboat Key Club offers additional golf, tennis, dining, fitness, spa, beach and social amenities depending on membership category.

3578 Fair Oaks Way, Longboat Key
$1,095,000
2 Beds ⋅ 2 Baths ⋅ A4704560 MLS ⋅ Beaches BLDG.
COMING SOON at Beaches of Longboat Key! According to Sarasota County property records, Unit 405 is a Gulf-front condominium featuring 2 bedrooms, 2 full bathrooms, and 1,602 square feet of living area. The building was constructed in 1984. Professional photography and additional property details will be added soon. Property information is based on public records and should be independently verified.

775 Longboat Club Road Unit 405, Longboat Key
$1,450,000
2 Beds ⋅ 2 Baths ⋅ A4706913 MLS ⋅ 2525 BLDG.
Welcome to your own piece of paradise at the renowned Islands West community on Longboat Key. This desirable 7th floor Gulf-side residence offers beautiful beachfront views, a thoughtfully designed floor plan, and the added peace of mind of hurricane impact windows and doors! The spacious interior features tile flooring throughout and two generously sized master suites, positioned on opposite sides of the residence to provide privacy for owners and guests. Both suites offer ensuite baths and beautiful Gulf views. The kitchen provides ample cabinetry and plenty of space for everyday living, while the main living area offers two separate seating areas and a defined dining space. With beautiful water views from every window, the home brings the natural beauty of the Gulf into everyday living. Step outside onto the spacious balcony and enjoy the coastal breezes, breathtaking Gulf views, and beautiful surroundings. It is the perfect spot to start the morning with coffee or unwind at the end of the day. Islands West offers an impressive collection of amenities, including a newly refurbished clubhouse, heated beachfront pool and hot tub, two fitness rooms, dry sauna, tennis and pickleball court, library, outdoor patio and grilling area, and beautifully landscaped grounds. Secure key-fob entry and direct access to the sandy Gulf beach complete the relaxed beachfront lifestyle. Ideally located on Longboat Key, Bay Isles Shoppes is just across the street, offering Publix, banking, dining, and everyday conveniences. St. Armands Circle, downtown Sarasota, area marinas, golf, and the beaches of Lido Key and Anna Maria Island are all within easy reach. Whether you are looking for a full-time residence, vacation retreat, or a place to enjoy the Florida lifestyle, this Gulf-side residence offers a wonderful combination of views, privacy, amenities, and location.

2525 Gulf Of Mexico Drive Unit 7B, Longboat Key
$989,000
2 Beds ⋅ 3 Baths ⋅ A4707277 MLS ⋅ Water Club BLDG.
Experience refined coastal living at The Water Club on Longboat Key, where lush tropical grounds meet the Gulf’s powdery white-sand beaches and shimmering aquamarine waters. Priced well below market value, this move-in ready, beautifully appointed Thomas Moser turnkey-furnished residence offers 2,000 square feet of thoughtfully designed living space, with two split-plan bedrooms, two full baths, a convenient powder room and a separate full-size laundry room with sink. Each spacious bedroom features a private en-suite bath, while 10-foot ceilings, warm wood flooring, and floor-to-ceiling hurricane-impact windows and sliders create an inviting sense of light and scale. The exceptional primary suite includes a generous walk-in closet and direct access to the private balcony. At the heart of the home, the expertly remodeled kitchen showcases custom cabinetry, a glass-mosaic backsplash, reverse-osmosis faucet, and premium stainless-steel appliances, including a Viking range and Sub-Zero refrigerator. A separate dry bar with Sub-Zero wine and beverage refrigerators adds effortless style for entertaining. The expansive terrace overlooks peaceful tropical foliage, offering a private setting for morning coffee or evening relaxation. Positioned on the plaza level, the residence provides convenient access to The Water Club’s world-class amenities, including 24-hour guard-gated security, concierge services, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and more than 16 acres of pristine beachfront grounds. Just a short drive from St. Armands Circle and downtown Sarasota, this distinguished residence places world-class dining, shopping, arts, and culture nearby. Discover timeless elegance, modern comfort, and an incomparable Gulf Coast lifestyle at The Water Club.

1241 Gulf Of Mexico Drive Unit 109, Longboat Key
$639,000
2 Beds ⋅ 3 Baths ⋅ A4706129 MLS ⋅ Na BLDG.
Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

539 Forest Way Unit 539, Longboat Key
$4,290,000
2 Beds ⋅ 3 Baths ⋅ A4702788 MLS ⋅ Champagne BLDG.
Tucked into the Champagne Building at The Residences at The St. Regis Longboat Key, unit 312 is a fully furnished coastal residence done right. Ceilings soar, glass walls stretch floor to ceiling, and the craftsmanship shows in every corner of this thoughtfully laid-out home. Step off the private elevator and into a great room capped by a dramatic tray ceiling and a sculptural bubble chandelier, where sliding glass doors open the space up to the terrace and the greenery beyond, letting the space extend beyond the walls. The kitchen is built for chef and entertainer alike. Glossy custom cabinetry, waterfall-edge counters with a leathered finish, a book matched quartz backsplash, and a full Wolf and Sub-Zero lineup, gas cooktop, double wall ovens, paneled refrigeration all give it the look of a showroom and the function of a real working kitchen. The island is the centerpiece for memories to be made with friends and family. The primary suite feels like its own retreat, tucked away from the living space with a wall of glass framing the grounds below. The bath is spa-worthy: dual vanities under illuminated round mirrors, a frameless glass rain shower, and a walk-in closet custom-fitted with enough drawers and shelving for a serious wardrobe. A second ensuite bedroom offers privacy for guests, and a well-appointed bath handles the rest. A discreet wet bar with wine storage and ice maker sits ready for evening cocktails, and wide-plank, wood-look porcelain tile runs throughout, warming up every room without competing with the views. Outside, the private terrace comes with its own Wolf gas grill, an easy spot for dinner under Longboat Key's evening skies. This is one of only 69 residences in the first branded residential community on the Gulf of Mexico with 800 feet of private beachfront. Ownership here comes with real perks: St. Regis Butler and Concierge service on call, a private Residents' Clubhouse and fitness center, a resident-only pool and spa, and beachside cabanas set aside just for owners. Steps beyond that, the full resort opens up: a heated infinity-edge pool, a drifting lazy river, a meandering saltwater lagoon home to a family of resident Aldabra tortoises, several chef-driven restaurants, and an oceanfront spa with vitality pools and a full menu of treatments. It's the kind of amenity list that makes staying home feel like a vacation. St. Armand’s Circle and downtown Sarasota are just minutes away, but out here on this stretch of Longboat Key, the pace slows down and the world feels a little further off. Here, you're not just buying a home, you're buying into the St. Regis way of doing life, every single day.

1591 Gulf Of Mexico Drive Unit 312, Longboat Key
$645,000
2 Beds ⋅ 2 Baths ⋅ A4706474 MLS ⋅ F BLDG.
LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style amenities all within your own community. Tucked into a private setting surrounded by tropical landscaping, this 2-bedroom, 2-bath second-floor end unit offers something buyers will appreciate immediately—extra natural light, added privacy, and no one living above you. Inside, the residence feels comfortable and welcoming, with an open living and dining area and a split-bedroom design that gives owners and guests their own space. The kitchen and bathrooms have been updated, the windows are newer, and a full-size washer and dryer inside the condo adds everyday convenience. The primary suite includes a walk-in closet plus a bonus area that works beautifully as a small home office, reading nook, or additional storage space. Florida living continues outdoors with two separate spaces to enjoy. Start the day on the open-air deck or relax on the screened lanai surrounded by Bayport's lush landscaping. Covered parking, guest parking, multiple storage areas, and an owner's closet provide even more functionality. But what truly sets this property apart is Bayport itself. Spanning approximately 27 acres from the Gulf of Mexico to Sarasota Bay, this distinctive Longboat Key community offers approximately 1,200 feet of private Gulf beach access along with an impressive collection of amenities. Spend the day at the heated Junior Olympic-size pool, play a match on one of four Har-Tru tennis courts, work out in the fitness center, launch a kayak onto the bay, or head to the fishing pier. When it's time for the beach, chairs and umbrellas are available for residents to enjoy. Bayport's winding pathways, mature tropical landscaping, and low-density setting create a peaceful atmosphere that feels worlds away—yet you're conveniently located to the restaurants, shopping, and attractions of Longboat Key, St. Armands Circle, and Sarasota. Beach in the morning, bay in the afternoon, and a Gulf sunset to finish the day. Whether you're looking for a full-time residence or a Longboat Key getaway, this is an opportunity to enjoy the island lifestyle from one exceptional Gulf-to-Bay community.

843 Bayport Way Unit 843, Longboat Key
$495,000
1 Baths ⋅ A4706240 MLS ⋅ Seahorse Beach Resort BLDG.
This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

3453 Gulf Of Mexico Drive Unit 237, Longboat Key
$599,900
2 Beds ⋅ 3 Baths ⋅ A4706685 MLS ⋅ N/A BLDG.
Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with a recently installed hurricane-rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). This property has been a second home for current long time owners, but similair neighboring properties boasts a proven track record as a lucrative short-term rental, consistently producing roughly $50,000 in net annual revenue after platform fees. Furthermore, it offers a rare level of operational flexibility for Longboat Key, permitting up to 26 rental cycles per year. When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front

521 Forest Way, Longboat Key
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