Siesta Key Homes with Pool View

Siesta Key Homes with Pool View

Welcome to Siesta Key, Florida—a picturesque barrier island that beckons with its stunning beaches, vibrant culture, and laid-back lifestyle. Nestled in Sarasota County, Siesta Key is renowned for its powdery white sands and crystal-clear waters, making it a tropical paradise for residents and visitors alike. Whether you're strolling along the iconic Siesta Beach or exploring the charming local shops and eateries, this enchanting island offers a unique blend of relaxation and adventure.

For those seeking the perfect home in this idyllic setting, Siesta Key boasts a variety of properties, including exquisite homes with pool views. Imagine waking up each morning to the gentle sound of water lapping against the shore, with a serene poolside oasis just outside your door. These homes not only provide a private retreat but also offer an ideal space for entertaining friends and family, basking in the glorious Florida sunshine, or simply unwinding after a day of beachcombing.

The real estate market in Siesta Key features a range of luxurious options, from modern contemporary designs to charming coastal cottages. Each home is designed to capture the essence of island living, with expansive windows that invite natural light and breathtaking views. Many of these properties come with private pools, allowing you to enjoy a refreshing dip at any time of day, all while soaking in the beauty of your surroundings.

Siesta Key is more than just a location; it’s a lifestyle. With its friendly community, outdoor activities, and cultural experiences, you’ll find that the homes with pool views here are not just houses—they're gateways to a vibrant and fulfilling way of life. Discover your dream home in Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Pool View

$699,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Experience the best of Siesta Key living in this beautifully renovated first-floor condominium at Beach Way. Located directly across from the world-famous Siesta Key Beach and just a short stroll to Siesta Key Village, this 2-bedroom, 2-bath residence offers the perfect combination of luxury, convenience, and investment potential. Inside, you'll find a thoughtfully updated interior featuring elegant quartz countertops, brand-new stainless steel appliances, durable Cali luxury vinyl plank flooring throughout, and a bright, open floor plan that flows seamlessly into the enclosed lanai. The lanai overlooks the tropical landscaping with a partial view of the community pool, creating the perfect place to relax after a day at the beach. Built for peace of mind, the unit features PGT WinGuard impact-resistant windows (Series 710) and PGT 700 Series impact-resistant sliding glass doors. Convenience continues outside with assigned covered parking located directly in front of the unit, along with ample guest parking for family and friends. Beach Way's desirable monthly rental policy makes this property an excellent option for a primary residence, vacation home, seasonal retreat, or income-producing investment. Enjoy resort-style coastal living just steps from the white quartz sand of world-famous Siesta Key Beach, with the Siesta Key Trolley stop conveniently located right in front of the community for effortless access to Siesta Key Village, shopping, dining, entertainment, and everything the island has to offer.

5600 Beach Way Drive Unit 109, Sarasota
$6,400,000
8 Beds ⋅ 9 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Steps from Siesta Beach. A brief stroll to the Village. A lifetime away from your tenants worries and cares. Prime Siesta Key investment opportunity or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence. Enjoy breathtaking Gulf sunrises and sunsets, a heated exotic lagoon-style pool with waterfall, Rocky Mountain quartz deck, professional tropical landscaping (updated 2024/2025), Miami-Dade impact windows/doors, newer roofs/insulation, and meticulous maintenance throughout. One building designed by renowned Lee Wetherington. Wake up to morning coffee overlooking the sugar-white sands, with Siesta Key Village shops and dining 0.5 miles away. Turnkey, versatile, and perfectly positioned for endless possibilities—your beachfront lifestyle awaits!

5610 Avenida Del Mare, Sarasota
$544,900
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Welcome to your own slice of paradise at Jamaica Royale on world-famous Siesta Key. This beautifully updated, turnkey one-bedroom, one-bath villa offers the convenience of ground-floor living in an all-ground-level association, meaning no stairs and no milestone inspections required. Renovated in 2025, this villa is move-in ready and ideally positioned with relaxing views. Jamaica Royale is a sought-after beachfront community featuring three swimming pools, private beach access with lounge chairs, grilling areas, shuffleboard, and a variety of recreational amenities, creating the perfect setting for both relaxation and fun. Whether you're searching for a personal beach retreat or a proven investment property, this villa delivers. With a strong rental history and existing bookings, it offers immediate income potential while giving you the opportunity to enjoy the sugar-white sands and turquoise waters of Siesta Key whenever you choose. As the best-priced turnkey one-bedroom villa currently available in Jamaica Royale, this is an exceptional opportunity to own a beachfront getaway at an outstanding value. Schedule your private showing today!

5830 Midnight Pass Road Unit 43, Sarasota
$2,600,000
4 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Stroll to the Village. Walk to the Beach. Cruise to the Gulf of Mexico. Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience, and the quintessential Siesta Key lifestyle are prepared for you to move in ready. A brief stroll from the vibrant energy of Siesta Key Village and the quartz sands of Siesta Beach. With an astounding approximately 240 feet of private seawall and offering long-range canal views creating a lagoon-like setting, this opportunity simply cannot be replicated. While offering crisp, clean lines of modern contemporary style, the infrastructure is strictly 2026-ready. This unique residence provides both luxurious aesthetic appeals, featuring a fully updated chef’s kitchen and designer baths, and "invisible luxury". The peace of mind that comes from the resilience of a durable metal roof, new seawall, and all-new high-velocity hurricane windows and doors, new flooring, wood burning fireplace, and new electrical, plumbing, as well as new three-zone HVAC and mechanical systems, has been thoughtfully provided. And, for your peace of mind, professional night vision high-tech security cameras and systems were installed in 2026. The preferred split plan offers three additional bedrooms, including a private guest suite with its own separate entrance and ensuite bath. Life at 339 Treasure Boat Way centers around the water. Venture out onto the paved, open-air pool deck to find a 2026 freshly re-finished Aqualink-controlled, saltwater, heated pool and spa with LED lighting. Enjoy gentle, golden morning sun and cool, shaded afternoons—perfect for entertaining and alfresco dining. An oversized detached two-car air-conditioned garage, fenced yard for pets, and ample guest parking.

339 Treasure Boat Way, Sarasota
$1,795,000
4 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Just bring your wardrobe! Welcome to this beautifully updated and fully furnished and equipped 4-bedroom, 3-bath cottage-style home in one of Siesta Key’s most sought-after neighborhoods - just a short stroll to public beach access at top-rated Siesta Key Beach. Meticulously renovated in 2025, this true turnkey entertainer's paradise offers a vacation-every-day lifestyle complete with thoughtful upgrades and everything you need to move right in. Inside you’ll find all-new tile flooring, fresh paint throughout, storm-rated windows, a new 310 Lennox air-conditioning system with a 10-year warranty, updated plumbing and electrical, a reverse-osmosis water system, a whole-house generator (gas or propane), and a newer roof (2021). The backyard oasis features a 50-foot saltwater pool, spa, and sundeck surrounded by elegant Italian marble, plus pool floats, basketball hoops, and a volleyball net for endless fun. Enjoy the outdoor shower, raised gardens, a Napoleon Prestige gas grill, fire table, electric vehicle charger, and a louvered pergola that opens or closes for perfect sun or shade, a 75-inch TV, and a Sonos outdoor surround sound system - ideal for outdoor movie nights. Ultimate privacy is provided by an 8-foot vinyl fence. The artificial turf in the front and backyard creates a clean and maintenance free living with a coastal feel. The gourmet kitchen is fully stocked and ready for entertaining, featuring 2025 Thermador appliances (refrigerator, stove top, dishwasher, and oven) plus a new LG washer and dryer. Practical extras include a Shark vacuum, clothes steamer, iron and board, and even towels, and washcloths already stocked in every bathroom. The home comes completely furnished with all shown décor, lamps, linens, and towels. Two of the bathrooms include bidets and large walk-in showers. Beach days are effortless thanks to the included beach chairs, towels, beach cart, and umbrella shade. A Ring camera system conveys with the home sale, offering peace of mind. Bonus: This home includes an assumable flood insurance policy for just under $4,700 annually. This is the fully equipped Siesta Key lifestyle you’ve been dreaming of. Call today to schedule your private showing!

5143 Sandy Beach Avenue, Sarasota
$649,900
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Ready to Enjoy the Great Life? Welcome to your own piece of paradise at Island Reef, one of Siesta Key's most sought-after Gulf-to-Bay Communities. Perfectly positioned in the desirable "A" Building, this beautifully maintained and furnished second-floor end unit offers breathtaking panoramic views of the Gulf of Mexico from the moment you walk through the door. Natural light pours into the residence, while expansive water views create a peaceful backdrop that defines true coastal living. Offering over 1,200 square feet, this two-bedroom, two-bath residence features a desirable split-bedroom floor plan that provides comfort and privacy for both owners and guests. Thoughtfully updated over the years and offered turnkey furnished, the condo is ready to enjoy immediately while still providing the opportunity to personalize over time. Whether you're preparing dinner with the Gulf as your backdrop, enjoying your morning coffee on the lanai, or ending the day with one of Siesta Key's unforgettable sunsets, every space is designed to embrace the waterfront lifestyle. Life at Island Reef extends well beyond your front door. Begin your mornings with a walk along the private beach at Turtle Beach, spend afternoons kayaking or paddleboarding through Little Sarasota Bay, or watch dolphins play in the Gulf from the community's beachfront pool. Boating enthusiasts will appreciate the community's bayside docks with lift capability and direct access to Sarasota Bay and the Intracoastal Waterway. Residents enjoy an impressive collection of resort-style amenities, including two heated pools, private beach access, tennis and pickleball courts, shuffleboard, a fitness center, clubhouse, library, fishing pier, kayak and bike storage, beautifully landscaped walking paths, on-site management, and covered parking. Ideally located on the quieter southern end of Siesta Key, Island Reef offers a relaxed coastal atmosphere while remaining just minutes from Siesta Key Village's dining, shopping, and entertainment. Don't forget to check out the complimentary trolley that goes directly to the village!! Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this is a Rare Opportunity to own a beautifully furnished & spacious Gulf-front Condominium in Island Reef one of Siesta Key's premier Gulf-to-Bay communities, where lush tropical landscaping, resort-style amenities, private beach access and unmatched Coastal lifestyle come together harmoniously to create the perfect place to feel at Home. Call today to Book a Private Showing - these opportunities don't last long!

8764 Midnight Pass Road Unit A201, Sarasota
$999,900
3 Beds ⋅ 2 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code
Experience Coastal Living at its finest in this turnkey-furnished, three-bedroom, two-bath retreat tucked away on a quiet cul-de-sac in a private community just minutes from the beach! This home features the ULTIMATE OUTDOOR living space with numerous updates offering the perfect blend of style, comfort, and low-maintenance lifestyle. As you step through the front door, you’re greeted by a bright open floor plan enhanced by tasteful coastal décor and tile flooring. Multiple dining and entertaining spaces flow effortlessly into the spacious family room, ideal for relaxing or hosting guests, with direct access to the stunning pavered pool area. The beautifully appointed kitchen features stainless steel appliances, abundant counter space, and a convenient breakfast bar for additional seating. Retire to the serene primary suite which offers a walk-in closet and a well-designed bath with dual sinks, and opens directly to the INCREDIBLE new 21' x 24' covered lanai—an inviting extension of your living space. This IMPRESSIVE private outdoor oasis features pavers, remote-controlled ceiling fans, sconce lighting, and a remarkable sunset overlooking the relaxing pool complete with dramatic lighting for that special ambience. Enjoy privacy and seclusion in your backyard retreat which is fully enclosed with a 7 foot vinyl fence. An outdoor shower adds convenience after a day at the beach. The exterior has been expertly refreshed with new hardiplank siding, fresh paint, and attractive stone accents. A premium landscaping package includes full irrigation, shell for low maintenance, and landscape lighting to set the perfect atmosphere. Additional upgrades elevate peace of mind and efficiency: a 2024 roof, hurricane-rated windows and doors, new pool pump, attic insulation, new garage door and opener, and a newly pavered front walkway and driveway with a charming sitting area and extra parking. This beautiful home reflects pride of ownership and detail with so many updates and most important no flooding during the storms! Ideally located close to Siesta Key Village, just one mile from world-renowned Siesta Key Beach, and near shopping, dining, and ODA school, this home is perfectly suited as a primary residence, vacation retreat, or exceptional rental opportunity!

783 Birdsong Lane, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Aloha Kai Apts SubDv. ⋅ 34242 Zip Code
Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Welcome to your island retreat just steps from world-famous Siesta Key Beach. This beautifully updated 2-bedroom, 1.5-bath villa offers the perfect combination of coastal living, investment potential, and resort-style amenities. Whether you're searching for a seasonal getaway, full-time residence, or income-producing property, this exceptional opportunity checks every box. Thoughtfully updated, the home features a newer metal roof (2020), impact-rated windows and front door, upgraded 200-amp electrical service, a 2023 water heater, and an updated kitchen with modern cabinetry, quality countertops, and newer appliances. Offered turn-key furnished, it's ready for immediate enjoyment or rental. The first floor experienced water intrusion during Hurricane Milton. Following the storm, the owners completed professional remediation, including a fully permitted renovation and independent mold testing with negative results. Documentation is available, providing confidence in the quality of the restoration. Nestled within the lush, tropical grounds of Aloha Kai, residents enjoy private deeded beach access to Siesta Key Beach, a heated Olympic-size swimming pool, clubhouse, shuffleboard courts, beautifully maintained landscaping, and on-site management. The community permits short-term rentals, making this an attractive opportunity for both personal enjoyment and investment income. Ideally located near Siesta Key Village, waterfront dining, shopping, boating, and all that Sarasota has to offer, this is your opportunity to own a move-in-ready beach villa in one of Florida's most desirable coastal communities. Buyer should verify all room dimensions, rental policies, and community regulations with the co-op association and management.

6020 Midnight Pass Road Unit 49, Sarasota
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 1142 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code
There is only one — Golden Set. Some residences embrace their surroundings. Others become an extension of them. Golden Set invites the island in—rich woods, woven textures, botanical motifs, and warm metallic accents establish a residence that feels both worldly and deeply rooted in Siesta Key. Your legacy, engineered for a lifetime of stories at a scale only you could imagine. This private resort centers around a breathtaking saltwater pool within its fully fenced backyard. Cross the sun shelf to the swim-up bar or unwind beneath the custom rock waterfall and built-in slide. Host championship matchups of pool volleyball or basketball, perfect your short game on the putting green, or dine alfresco beneath covered seating with multiple televisions and a state-of-the-art outdoor kitchen. Inside, nearly 3,600 square feet unfold across multiple levels connected by a private elevator. The great room serves as the social heart of the home – an exceptional setting for gatherings while the chef’s kitchen supports your culinary imagination. Festivities transition effortlessly from the expansive living and dining areas onto the terrace, blending the boundary between indoor elegance and outdoor paradise. The upper levels are devoted to privacy in four en-suite guest rooms and multiple viewing balconies. At the pinnacle of the residence lies its most exclusive destination. A well-appointed club room, complete with a half bath, creates an elevated entertainment hub, while the rooftop terrace, perched 50 feet above the island, is the final expression - sunrise over Siesta Key, long afternoons beneath the island sun, and evenings illuminated by the fading glow of the Gulf horizon. The secluded primary suite occupies the home's most private position, delivering breathtaking Gulf views, a spa-inspired bath, and the rare luxury of complete retreat. Here, your final view of the day is nothing short of spectacular. More than a home, Golden Set is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.

1142 Windsong Lane Unit B, Sarasota
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 1140 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code
There is only one — Siesta Springs. Some homes provide an escape. Others invite renewal. Inspired by the restorative rhythm of island living, Siesta Springs is a residence where every detail feels fresh, intentional, and connected to its surroundings. Driftwood-inspired finishes, layered coastal hues, and natural textures create a home that feels both contemporary and timeless—capturing the effortless spirit of Siesta Key without relying on convention. Designed to unfold naturally from one experience to the next, the residence balances vibrant gathering spaces with moments of quiet retreat. From private beach access and a lagoon-style pool to elevated terraces overlooking the Gulf, each level offers a new perspective while remaining connected to the whole. Across nearly 3,600 square feet and five levels connected by elevator access, the home encourages a lifestyle defined by movement, connection, and ease. The experience begins outdoors, where a resort-inspired backyard retreat features a cascading rock waterfall, custom slide, rope swing, sun shelf, ample covered patio seating with an outdoor kitchen, and lush landscaping. Here, recreation and relaxation exist in perfect balance. Inside, natural materials and modern finishes establish a sense of effortless sophistication. Driftwood-inspired flooring extends overhead, creating warmth and continuity throughout the residence, while shades of blue and gray evoke the colors of the shore beyond. A chef's kitchen supported by a dedicated scullery anchors the great room, where gatherings flow seamlessly onto expansive terraces and outdoor living spaces. Five en-suite bedrooms provide private retreats throughout the home, including a playful bunk room complete with a climbing wall—an unexpected detail that reinforces the home's spirit of energy and discovery. At the highest level, a club room designed for games, conversation, and connection opens to a rooftop terrace where sunrise and sunset become part of the daily rhythm. Nearby, the primary suite occupies the home's most private position, offering Gulf views, exceptional privacy, and a spa-inspired bath designed for restoration. More than a home, Siesta Springs is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.

1142 Windsong Lane Unit A, Sarasota
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed to celebrate both architectural craftsmanship and the beauty of its remarkable setting. A protected deep-water harbor, a private 50-foot dock and 20,000-pound lift create an exceptional opportunity for the serious boater, while the home’s privacy, scale and resort-style outdoor living make it equally ideal as a serene waterfront retreat. From the moment you arrive, custom mahogany doors, beveled glass transoms, lush landscaping and a gracious entry introduce the timeless character found throughout the residence. Inside, soaring ceilings, generous room proportions and walls of glass frame magnificent water views from many of the principal living areas. Rich architectural details include coffered and tray ceilings, bentwood arches, crown molding, custom millwork and travertine inset flooring. The formal living and dining rooms flow beautifully for entertaining and are complemented by a fully outfitted cherrywood-paneled bar and wine room. The executive office and library are a showpiece, featuring cherrywood paneling, an 18-foot coffered ceiling and a spiral staircase leading to upper bookshelves. The well-appointed island kitchen offers Wood-Mode cabinetry, quartzite countertops, stainless steel appliances, paneled Sub-Zero refrigeration, a Viking six-burner gas range, dual ovens, a walk-in pantry and a spacious breakfast bar. Open to the bayfront breakfast and gathering rooms, the space features an electric fireplace, adding warmth and ambiance, and connects effortlessly to the outdoor living areas. The primary suite is a private waterfront sanctuary with a bayfront sitting room and a generous bath with dual vanities, a two-person shower, a soaking tub and private water closets. Two additional guest suites are privately positioned in their own wing on the main level, along with a powder bath and laundry room. Upstairs, a fourth bedroom or game room includes a full bath, walk-in closet and private western balcony overlooking the harbor, ideal for taking in evening sunsets. Designed for relaxed Florida living, the expansive lanai features a heated saltwater infinity-edge pool, travertine decking and a shaded outdoor living space with custom ceiling detail, creating an inviting setting for alfresco dining and waterfront entertaining. Frequent dolphin and manatee sightings add to the magic of this rare waterfront setting. Additional features include a side-entry three-car garage, a paver drive and walkways, landscape lighting, a walk-in attic and abundant storage. Hidden Harbor is one of Siesta Key’s most treasured boating communities, offering exceptional privacy just one mile from the powdery white sands of Siesta Beach and close to Siesta Village’s dining, shopping and island charm. Mainland Sarasota’s cultural venues, restaurants, shopping, medical facilities and schools, including nationally acclaimed Pine View School, are also within easy reach.

1280 Hidden Harbor Way, Sarasota
$1,600,000
2 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Your island escape awaits! Masterfully renovated and beautifully styled, this turnkey-furnished and move-in ready 2-bedroom, 2-bathroom, 1-car garage pool/spa coastal residence offers an unmatched island lifestyle on Siesta Key. Positioned on a tranquil residential street, this beautiful home sits at the intersection of privacy and prestige—just moments from the culinary delights of Siesta Village and the iconic white Quartz sands of Siesta Beach. The interior design embraces a bright, open floor plan defined by a sophisticated coastal color palette and seamless indoor-outdoor integration. At the heart of the home is the gourmet kitchen, featuring premium Cambria quartz countertops, classic farmhouse sink, and luxurious Wolf and Sub-Zero appliances. Thoughtful details include subway tile backsplash, a wine refrigerator, convenient pot filler, and custom soft-close cabinetry. Retreat to the primary bedroom suite, featuring a custom walk-in closet and an elegantly appointed en-suite bath with a granite-topped double-sink vanity and a beautifully tiled walk-in shower. Guests will enjoy total privacy in the secondary bedroom and guest bath with shower over tub. Outside, the screened lanai functions as an outdoor living room, offering views of the heated saltwater pool, integrated spa, and manicured tropical grounds, lovely in the evenings with custom outdoor lighting. Every detail has been upgraded for maximum comfort and durability, from the impact-glass windows and doors to plank tile flooring throughout, new laundry room with front-load Samsung washer & dryer and a high-efficiency tankless water heater. Boasting a proven location with income potential exceeding $100,000 per year, this property represents a rare opportunity as an excellent investment or your ideal seasonal or permanent home. No HOA! Schedule your showing today!

810 Plymouth Street, Sarasota
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