Siesta Key Homes with Pool View

Siesta Key Homes with Pool View

Welcome to Siesta Key, Florida – a stunning barrier island that offers the perfect blend of sun, sand, and serenity. Nestled in Sarasota County, Siesta Key is renowned for its powdery white beaches, vibrant nightlife, and charming coastal community. With its tropical climate and picturesque scenery, it's no wonder that this island paradise attracts visitors and residents alike, all seeking the ultimate Florida lifestyle.

One of the most appealing features of Siesta Key is its diverse selection of homes, particularly those with captivating pool views. Imagine waking up in your dream home, where the gentle sound of water splashing and the sight of shimmering pools become part of your daily routine. Homes with pool views in Siesta Key offer not just a place to live, but a lifestyle that embodies relaxation and leisure. Whether you’re sipping your morning coffee by the poolside or hosting an unforgettable sunset gathering with friends, these properties provide the ideal backdrop for both tranquil mornings and lively evenings.

The real estate market in Siesta Key is as vibrant as the community itself, with options that cater to various tastes and budgets. From luxurious beachfront estates to cozy condos nestled among lush landscapes, there’s something for everyone. Plus, with the beach just a stone's throw away, residents can easily enjoy the sun-kissed shores and vibrant local culture.

Discover the allure of Siesta Key and explore the homes with pool views that await you. Your slice of paradise is just a visit away!

Newest Siesta Key Homes with Pool View

1140 Windsong Lane Unit A, Sarasota
$3,995,000
5 Beds ⋅ 7 Baths ⋅ 1140 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code
What if your next luxury vacation home could be just as rewarding when you're away as when you're enjoying it yourself? Welcome to Blue Lagoon, an ultra-high-performing short-term luxury vacation rental on Siesta Key, purpose-built to deliver the best of both worlds: an extraordinary private coastal retreat and a compelling income-producing asset. Your home. Your schedule. Your decision. Built in 2024 and offered turnkey furnished, this five-bedroom, seven-bath residence delivers 3,891 square feet of sophisticated coastal living, with beautifully curated interiors, an expansive gathering kitchen, five en-suite bedrooms, private elevator, and multiple terraces overlooking the island. But the real magic? Step outside. A spectacular private lagoon awaits, complete with a rock waterfall, waterslide, rope swing, jumping platform, and heated saltwater pool, accompanied by outdoor entertaining spaces, miniature golf, and bocce. Above it all, a rooftop terrace captures Gulf views, while deeded beach access places Siesta Key's celebrated shoreline just moments away. Part of Vunique's distinctive collection of luxury vacation homes, Blue Lagoon combines commercial-grade durability with residential sophistication, engineered for the demands of luxury vacation rental performance without compromising the pleasures of private ownership. Enjoy it exclusively, capitalize on its rental potential, or find your own balance between the two. An exceptional lifestyle. A compelling investment. Entirely your decision.

1140 Windsong Lane Unit A, Sarasota
1142 Windsong Lane, Sarasota
$7,900,000
10 Beds ⋅ 14 Baths ⋅ 1350 Main Residential SubDv. ⋅ 34242 Zip Code
What if your next luxury real estate investment was just as rewarding to own as it was to enjoy? Welcome to Golden Springs Estate, an ultra-high-performing short-term luxury vacation rental on Siesta Key, generating well over half a million dollars in annual gross rental revenue, where the lines between private coastal retreat and income-producing asset become beautifully blurred. Comprising two distinct, turnkey luxury residences, this 2024-built estate delivers 10 bedrooms, 14 bathrooms, 7,782 square feet of interior living space, and an extraordinary collection of amenities designed for entertaining on a grand scale. Think two private saltwater pools, rooftop terraces with Gulf views, private elevators, expansive outdoor living, and deeded beach access just moments away. Two residences. Twice the possibilities. Purpose-built for the luxury vacation rental market, each residence is fully self-contained and independently functional, separated by a common wall yet offering the privacy and autonomy of an individual home. Capitalize on the income potential of both residences, live in one full-time while the other generates revenue, or create a multigenerational coastal retreat with the freedom to accommodate family and guests without sacrificing privacy. Part of Vunique's distinctive collection of luxury vacation homes, this is an opportunity to think beyond conventional real estate ownership. An exceptional lifestyle. A compelling investment. Entirely your decision. Each residence may also be purchased separately. Contact your real estate professional for additional information.

1142 Windsong Lane, Sarasota
6006 Midnight Pass Road Unit 48, Sarasota
$325,000
1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Virtually Staged. Your Slice of Paradise Awaits at Casa Mar on World-Famous Siesta Key! Location, location, location! Welcome to Casa Mar, a highly desirable beachfront condominium community on the world-renowned shores of Siesta Key! This charming studio condominium offers the perfect combination of coastal living, resort-style amenities, and excellent rental income potential. Ideally situated just 100 feet from the beautiful white quartz-sand beach, this inviting retreat also enjoys a wonderful view overlooking the sparkling community pool, creating the perfect tropical setting for your very own piece of paradise! Inside, you'll find a comfortable and inviting living space featuring thoughtful kitchen updates, including updated lower kitchen cabinetry, beautiful quartz countertops, and a stainless-steel sink. Whether you're looking for a personal beach getaway, an income-producing investment, or a combination of both, this studio offers an incredible opportunity to own in one of Florida's most sought-after vacation destinations. Casa Mar is truly a hidden gem on Siesta Key! This established beachfront community offers an impressive array of resort-style amenities, including approximately 300 feet of private deeded beachfront, two swimming pools, covered beachfront pavilions, tennis and pickleball courts, shuffleboard, beach volleyball, BBQ grilling areas, picnic spaces, and beautifully maintained tropical grounds. Spend your mornings strolling along the powdery white sand, your afternoons relaxing poolside, and your evenings enjoying spectacular Gulf Coast sunsets just steps from your door! The location is simply outstanding! Nestled along desirable Midnight Pass Road, Casa Mar offers the perfect blend of peaceful beachfront relaxation and convenient access to everything Siesta Key and Sarasota have to offer. Enjoy nearby waterfront dining, charming boutiques, lively entertainment, and the vibrant atmosphere of Siesta Key Village. The free Siesta Key Breeze Trolley makes exploring the island a breeze, while the shopping, dining, arts, and cultural attractions of downtown Sarasota are just a short drive away. Investors take note! With Siesta Key's worldwide reputation as a premier vacation destination, Casa Mar's desirable beachfront setting, extensive amenities, and rental appeal make this an exciting opportunity for those seeking potential rental income. Enjoy the flexibility of a vacation retreat while exploring the income-producing possibilities of this sought-after location. Opportunities like this are all about location, lifestyle, and value! Whether you're dreaming of carefree days at the beach, a relaxing winter escape, or a desirable investment property, this Casa Mar studio delivers the quintessential Siesta Key experience. With the beach just steps away, a beautiful pool view, and outstanding amenities at your fingertips, paradise is calling! Don't miss your opportunity to own a little piece of world-famous Siesta Key!

6006 Midnight Pass Road Unit 48, Sarasota
5830 Midnight Pass Road Unit 61, Sarasota
$560,000
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
An unrivaled BEACHFRONT lifestyle meets incredible value on Siesta Key. Positioned at a new, highly competitive price point, this fully remodeled ground-floor villa represents one of the most accessible opportunities to own directly on the Gulf of Mexico. Tucked away within the coveted Jamaica Royale community, your days here begin with gentle waves on a private sugar-white sand beach and end with spectacular, lingering island sunsets. Every inch of this 728-square-foot layout has been completely transformed to live significantly larger than a typical one-bedroom beach home. The interior boasts a beautifully redesigned kitchen featuring brand-new lower cabinetry and premium granite countertops, a fully upgraded primary bathroom, new base trim, and fresh interior doors. Absolute peace of mind is built right in with brand-new, impact-engineered doors and windows, alongside a comprehensive suite of new appliances and mechanicals—including the refrigerator, dishwasher, washer, dryer, A/C unit, and water heater. Ownership here is uniquely effortless. Quarterly dues handle the upkeep and include cable, water, and sewer for predictable, stress-free carrying costs. Unlike most beachfront communities, Jamaica Royale is proudly pet-friendly, allowing you to share the island life with your dog. Spend your afternoons lounging in a private beachside cabana, swimming in one of the three heated pools, or utilizing the beachside BBQ grills. When you're ready to explore, public transit connects you seamlessly to Siesta Village, downtown Sarasota, and Gulf Gate. Whether you are seeking a pristine personal retreat, a high-performing investment, or both, this villa is fully turnkey and ready to enjoy. Schedule your private tour today to experience this rare Gulf-front value firsthand. Incentive Note: A 1% rate reduction is available to qualified buyers who work with the seller's preferred lender.

5830 Midnight Pass Road Unit 61, Sarasota
67 Avenida Messina Unit B, Sarasota
$3,900,000
5 Beds ⋅ 5 Baths ⋅ Sunset Point Villas SubDv. ⋅ 34242 Zip Code
Rising four stories above Siesta Key, this exceptional turn-key coastal villa transforms Gulf panoramas into a captivating backdrop for daily life. Privately situated within Mira Mar’s gated enclave of only four residences, this 3,824-square-foot unit offers the distinction of Siesta Key living just steps from Beach Access Number 2. Expansive windows and glass doors invite sunlight throughout while revealing Gulf views from every level. In the living room, corner windows and French doors lead to a balcony where coastal breezes set an effortless rhythm. The sunlit kitchen pairs sleek cabinetry with a sculptural curved island, while broad windows frame lush tropical scenery. Five bedrooms and five full bathrooms unfold across four levels, providing generous accommodations for family and guests. Every room but one has a separate balcony for taking in those beautiful sunsets or perhaps your morning coffee. A private elevator makes each floor easily accessible, an elegant convenience when the rooftop is calling. Abundant storage supports everyday organization, and the spacious garage accommodates two vehicles along with dedicated space for a boat/jet ski or golf cart. Crowning the residence, the rooftop terrace presents a spectacular stage for sunset soirées, with sweeping Gulf vistas commanding attention. A covered balcony with streamlined railings offers another inviting setting for savoring the salt air and luminous coastal surroundings. Beyond the gates, Siesta Village places live music, open-air dining, and charming local establishments moments away, while Morton’s Siesta Market is approximately 0.3 miles from home. Claim a rare intersection of privacy, beach proximity, and elevated island living. Schedule your private showing and discover life above the ordinary.

67 Avenida Messina Unit B, Sarasota
4938 Commonwealth Drive, Sarasota
$2,650,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Exceptional luxury coastal living on Siesta Key! Positioned on Siesta Key’s Grand Canal with quick access to Sarasota Bay, this fully renovated estate offers the perfect blend of high-end comfort and modern efficiency. Powered by solar panels with battery storage, this eco-conscious home delivers peace of mind and low utility costs. The sprawling open floor plan highlights a newly integrated primary guest suite and seamless indoor-outdoor flow opening to a resort-style heated cocktail pool and spa. A standout feature is the expansive, grandfathered 1,300 sq. ft. bonus space—providing endless possibilities for a game room, home gym, or customized lounge. Complete with high-end boating amenities and located just minutes from world-famous Siesta Key Beach and Village. Move-in ready perfection!

4938 Commonwealth Drive, Sarasota
6910 Midnight Pass Road, Sarasota
$5,400,000
10 Beds ⋅ 14 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
TWO LUXURY RESIDENCES. ONE SIESTA KEY ESTATE. OVER HALF A MILLION IN 2025 GROSS RENTAL REVENUE. Rent them. Keep them for yourself. Or enjoy the best of both worlds. Welcome to 6910 Midnight Pass Road, where luxury coastal living meets proven investment performance at less than 10× GRM. Just moments from Crescent Beach and iconic Point of Rocks, this remarkable offering features ten bedrooms, fourteen bathrooms, 5,767 square feet of living space, private elevators, resort-style pools and spas, and expansive indoor-outdoor entertaining spaces. Purpose-built as luxury short-term vacation rentals, both residences blend sophisticated coastal design with commercial-grade durability and resort-level amenities. Built for memories. Engineered for performance. With historical average daily rental rates exceeding $1,000, approximately 250 booked nights annually per residence, and potential STR-related tax strategies worth exploring with your tax advisor, this is more than a vacation home. It's an asset with options. Currently configured as two separately titled condominium residences, offered together as a single purchase. Financial performance and rental history available upon request

6910 Midnight Pass Road, Sarasota
1001 Point Of Rocks Road Unit 207, Sarasota
$1,599,900
3 Beds ⋅ 2 Baths ⋅ Siesta Sands Resort (Timeshare) SubDv. ⋅ 34242 Zip Code
Gulf views from the primary bedroom, or step onto your attached patio with your morning coffee and watch the water come alive. This completely renovated 3 bedroom, 2 bath townhome style condo is turn key and furnished, with an open split floor plan and natural Florida sunlight throughout. The renovation is top to bottom: plank tile floors, solid wood cabinetry, marble countertops, upgraded backsplash, barely used appliances, fresh paint, fully renovated baths with custom tile, new hardware, and new lighting throughout. All windows, doors, and sliders are hurricane impact. Three patios let you soak up the Florida sunshine and Gulf breezes, with the residence facing the pool and open to full Gulf views. Extras include air conditioned storage off the patio, a large laundry room, and an assigned carport with storage and electric hookup. This gated resort offers private beach access, two heated pools, a poolside gazebo with BBQ grills, a lounge area, a fitness room, and high speed WiFi. Walk the sand to Point of Rocks to snorkel and fish, bike to nearby shops and restaurants, or hop the free island trolley to Siesta Key Village. One of the island’s top performing rental communities, with short term rentals allowed (3 day minimum), an on site office, or your own rental service. On site management reports that 3 bedroom units in the community rent for approximately $6,000 per week at the height of season. Rental rates are not guaranteed and are subject to change. A private beachside retreat, a seasonal escape, or a legacy asset to hold and pass down. Bring your flip flops.

1001 Point Of Rocks Road Unit 207, Sarasota
6512 Midnight Pass Road Unit 206, Sarasota
$1,690,000
2 Beds ⋅ 2 Baths ⋅ Crescent Siesta Key SubDv. ⋅ 34242 Zip Code
Experience Luxury Living on South Siesta Key! Welcome to your dream condominium, perfectly situated on the pristine shores of Siesta Key. This stunning Gulf-front property offers unparalleled beach living, making it the ultimate coastal retreat. This corner unit is offered turnkey furnished, ready for immediate enjoyment. Impeccably designed in a contemporary beachfront style, the 1,600-square-foot, two-bedroom, two-bath residence presents an expansive floor plan highlighted by a gourmet kitchen featuring top-tier appliances, granite countertops, soft-close cabinets and refined accents. The kitchen seamlessly transitions into a spacious living area accented by an artistic terrazzo accent wall opening onto an expansive terrace. Your terrace has a built-in outdoor kitchen, gas grill and private access to the resistance-heated lap pool with child safety fence/doors. The terrazzo wall continues through both bedrooms, adding a sophisticated beach ambiance. The primary bath featuring dual sinks, a private toilet with automatic bidet amenities, a deep soaking tub and a large walk-in shower. The additional bedroom for your guests includes an ensuite bath, which offers ample space. Wifi and remote-controlled thermostat, door lock, gate, building and beach access. Plus two owner’s storage closets for rental convenience. This property serves as a tranquil retreat in an exceptional location, very quiet with very little street noise, whether you're seeking a permanent residence, a vacation getaway or a profitable rental property. The building boasts an array of amenities designed to elevate everyday living, including onsite management for added convenience and closed-circuit camera/surveillance systems for security. Residents can enjoy a beachfront heated pool, spa and resistance lap pool right outside your door. A fitness center ensures residents stay active. Dive into one of two pools or spas overlooking the beach, enjoy the white sugar sand beaches that stretch for miles, create fabulous meals in the outdoor kitchen and dine al fresco with a view of the gulf amidst beautifully landscaped gardens or sink into a chaise lounge under the loggias with a great book. At Crescent Siesta Key, embrace a lifestyle of comfort, luxury and seaside serenity with all amenities conveniently at your disposal.

6512 Midnight Pass Road Unit 206, Sarasota
1207 Sharswood Lane, Sarasota
$3,195,000
3 Beds ⋅ 4 Baths ⋅ Spice Bay SubDv. ⋅ 34242 Zip Code
LIVE THE SIESTA KEY LIFESTYLE IN SPICE BAY—an intimate, gated enclave of just 14 estate-sized homesites in one of Siesta Key’s most distinctive Intracoastal communities. Custom built by award-winning builder Ryan Perrone of Nautilus Homes, this sophisticated residence offers approximately 3,235 square feet of beautifully designed SINGLE-LEVEL LIVING with exceptional craftsmanship, privacy, and effortless indoor-outdoor entertaining. Offered FURNISHED, this exceptional home is ready for you to immediately begin enjoying the Siesta Key lifestyle. From the moment you enter through the impressive mahogany front door, a dramatic wall of glass sliders draws your eye to the lush tropical surroundings and expansive outdoor living areas beyond. Filled with NATURAL LIGHT, the home blends refined finishes with relaxed “barefoot elegance,” creating a coastal retreat that feels both luxurious and inviting. The thoughtfully designed floor plan features 3 BEDROOMS, EACH WITH ITS OWN ENSUITE BATH, providing exceptional privacy and comfort for family and guests. The spacious primary suite includes a private den/study and a luxurious spa-inspired bath, while the additional bedrooms are generously sized and beautifully appointed. A PRIVATE CASITA LOCATED JUST OFF THE PORCH adds even more flexibility—perfect for visiting guests, extended family, a private retreat, studio, or home office. Throughout the home, you’ll find wide-plank oil-finished wood flooring, handcrafted details, custom closets and built-ins that reflect the quality of this custom residence. At the heart of the home, the GOURMET CHEF’S KITCHEN was created for entertaining and features a 6-burner gas range, steam oven, two dishwashers, generous workspace and a large walk-in pantry. Open the sliders and embrace true Florida indoor-outdoor living. The extended courtyard and lanai enjoy DESIRABLE SOUTHERN EXPOSURE and a private tropical setting—perfect for morning coffee, entertaining friends, relaxing with an evening cocktail or unwinding in the spa. For boating enthusiasts, enjoy access to a DEEP-WATER BOAT DOCK WITH A 13,000-LB LIFT, making it easy to spend your days exploring Sarasota Bay and the surrounding waterways. An oversized THREE-CAR TANDEM GARAGE provides exceptional space for vehicles, storage and all your island toys. Spice Bay offers the rare combination of PRIVACY AND CONVENIENCE on Siesta Key. Walk or bike to the beach, nearby shops and restaurants, spend your days enjoying the world-famous quartz sands of Siesta Key Beach, then head downtown for Sarasota’s celebrated dining, arts and cultural scene. This exceptional TURNKEY FURNISHED custom residence captures the very best of luxury coastal living—private, refined and unmistakably Siesta Key.

1207 Sharswood Lane, Sarasota
8773 Midnight Pass Road Unit 504G, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota
3458 Anglin Drive, Sarasota
$2,495,000
4 Beds ⋅ 3 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code
Located in the highly desirable Bay Island neighborhood, this beautifully updated, move-in-ready Key West-style residence offers an appealing combination of privacy, space, and convenience. Known as the "Gateway to Siesta Key," Bay Island enjoys a prime location near the north bridge, providing easy access to Siesta Key's beaches and village, as well as downtown Sarasota's dining, shopping, and cultural attractions. Set on an expansive 14,400-square-foot double lot—an uncommon offering on Siesta Key—the property is surrounded by mature tropical landscaping, creating a private setting with generous outdoor living spaces. The home's open floor plan features vaulted ceilings, abundant natural light, and a natural gas fireplace. French doors connect the main living areas to multiple covered terraces, extending the living space outdoors. The kitchen features a large quartzite island, custom cabinetry, generous storage, and a full suite of Thermador appliances. The primary suite is located on the main living level, along with a flexible fourth bedroom or den. On the third floor, two spacious guest bedrooms share a newly renovated bathroom and enjoy access to an elevated terrace. Outdoor amenities include a heated saltwater pool, travertine decking, an outdoor shower, and ample space for relaxing or entertaining within the landscaped grounds. Extensively renovated in 2019 and further improved in subsequent years, the home features updated major systems, hurricane-rated windows and French doors, retractable screens, whole-house water filtration, and additional upgrades. Meticulously maintained and move-in ready, this Bay Island property offers an uncommon combination of lot size, privacy, location, and updated living spaces on Siesta Key.

3458 Anglin Drive, Sarasota
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