Siesta Key Homes with Pool Amenities

Siesta Key Homes with Pool Amenities

Welcome to Siesta Key, Florida—a tropical paradise that effortlessly blends stunning natural beauty with a vibrant community spirit. Nestled in Sarasota County, Siesta Key is renowned for its powdery white sand beaches, breathtaking sunsets, and a laid-back lifestyle that attracts visitors and residents alike. This enchanting barrier island is not just a haven for beach lovers; it offers a rich tapestry of dining, shopping, and recreational activities, making it a perfect destination for families, retirees, and anyone seeking a serene escape.

One of the most sought-after features in Siesta Key real estate is the abundance of homes with pool amenities. Imagine stepping out of your beautifully designed home into your own private oasis, where you can bask in the sun, take a refreshing dip, or host unforgettable gatherings with friends and family. Many of these homes are strategically located just a stone's throw away from the beach, allowing you to enjoy the best of both worlds: the tranquil allure of your poolside retreat and the invigorating ocean waves.

Whether you're looking for a luxurious waterfront property or a cozy retreat tucked away in a lush landscape, Siesta Key’s real estate market offers a diverse range of options to suit your lifestyle. With the gentle gulf breeze and the promise of endless sunshine, your dream home in Siesta Key awaits. Embrace the opportunity to create lasting memories in this idyllic coastal haven, where every day feels like a vacation. Discover the charm of Siesta Key—your perfect slice of paradise!

Newest Siesta Key Homes with Pool Amenities

4712 Ocean Boulevard Unit W5, Sarasota
$1,359,000
2 Beds ⋅ 2 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Virtually Staged - Perfectly positioned to capture the ever-changing beauty of the Gulf, this northwest-facing residence offers a front-row seat to nature’s daily masterpiece. From the lush green lawn and swaying palm fronds to the Gulf’s ever-changing shades of turquoise, blue, and emerald, the views unfold in layers of coastal color. As the day draws to a close, the western sky ignites in brilliant sunset hues, transforming the landscape into a breathtaking panorama that never looks quite the same twice. Here, the view isn’t just something you see—it’s an experience to savor. Welcome to Windward Passage, where the beauty of Siesta Key meets the comfort of an exceptionally spacious coastal retreat. Offering 1,626 square feet of living space, this two-bedroom, two-bath residence blends timeless Gulf views with thoughtful modern updates. Renovated kitchen and bathrooms, luxury vinyl plank flooring throughout, impact-resistant windows, and a newer air-conditioner provide the perfect balance of style, comfort, and peace of mind. Situated on the third floor, the home enjoys an ideal elevation—high enough to embrace sweeping coastal scenery while maintaining a wonderful connection to the tropical landscape below. An oversized private garage adds a level of convenience and storage rarely found in condominium living. Beyond the residence, the best of Siesta Key is practically at your doorstep. Just a leisurely 10-minute stroll brings you to the heart of Siesta Key Village, where lively tiki bars, exceptional dining, boutique shops, and live music create an atmosphere that’s distinctly island. And when the beach calls, the nearest public beach access lies just beyond "The Village" or an even easier 5-minute bike ride away. Whether you’re seeking a full-time residence or a cherished coastal getaway, this is a place to slow down, settle in, and appreciate the extraordinary beauty of everyday life on Siesta Key. Some properties are defined by their features. Others are remembered for how they make you feel. This one offers both.

4712 Ocean Boulevard Unit W5, Sarasota
120 Whispering Sands Drive Unit V20, Sarasota
$725,000
3 Beds ⋅ 3 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
RARELY AVAILABLE & EXQUISITELY REMODELED! Discover an exceptional 3 bedroom/3 bath freestanding villa with 2-car garage in Whispering Sands, Siesta Key’s coveted resort style GULF FRONT community on 800’ of private beach! Completely gutted and reimagined in 2016, this remarkable residence showcases creative design, quality finishes, and meticulous attention to detail throughout. An impressive 1,640 square feet of interior living space unfolds beneath soaring vaulted ceilings, with an open concept layout designed for effortless living and entertaining. The expansive 16' x 22' living room is delightfully complemented by sophisticated indirect LED illumination. Beautiful ceramic plank flooring flows throughout. The spacious entertainer’s kitchen combines style and function with granite countertops, a generous breakfast bar, soft close cabinetry & pullout drawers, LG and Bosch stainless appliances, and recessed and pendant lighting. The spacious primary suite offers two closets – a custom walk-in and a separate built-in. The third bedroom could also easily function as a home office, featuring a built-in desk, shelving, and custom closet. All three beautifully remodeled bathrooms feature granite counters, soft close cabinetry, tiled glass-enclosed walk-in showers, recessed lighting, and/or skylights. Two out of three bathrooms are ensuite — a rare advantage. All 2016 hurricane impact windows and sliders. Extend your entertaining outdoors into the private fenced brick paver patio, complete with a gas grill, with propane tank and gas hookup. The epoxy finished 2-car garage includes a full size LG washer and dryer, utility sink, workbench and shelving – and plenty of space for your bikes and beach essentials. Enjoy the Whispering Sands lifestyle. Just around the corner from famous Siesta Key Village, this 55+ Gulf front community includes 800’ of private quartz sand beach, two heated pools, clubhouse (currently undergoing complete remodeling), beachside Tiki Hut, shuffleboard, and canoe/kayak storage. Don’t miss this distinctive villa offering exceptional space, privacy, and effortless coastal living!

120 Whispering Sands Drive Unit V20, Sarasota
6310 Midnight Pass Road Unit 403N, Sarasota
$749,000
2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code
Dont Miss this one' beachfront Unit at Crescent Arms on beautiful Siesta Key. Wake up to the sound of gentle waves and step directly onto the powdery white sands of world-renowned Siesta Key Beach from this beautifully fourth floor unit. Perfectly positioned for effortless coastal living, this 2-bedroom, 2-bath unit offers Gulf views and a short walk-out to the beach. The open-concept layout is bathed in natural light, featuring a spacious living area that flows seamlessly to the screened lanai, you can enjoy sunsets over the Gulf . This unit was updated several years ago with solid-surface countertops, tiled floors through out and ample storage making it ideal for both full-time living and vacation stays. The primary suite boasts ample room for a king bed which will boost rental income and a private ensuite bath, while the guest bedroom and bath provides comfort and privacy for family or visitors. Crescent Arms offers resort-style amenities, including a heated beachside pool, private beach lounges, grilling area, and gated access for security and peace of mind. Located on Siesta Key, this community is within minutes of Siesta Key Village, shops, restaurants, and island nightlife. Whether you’re seeking a serene retreat, an investment property with excellent rental potential, or your forever beach home, this beachfront gem delivers the ultimate Siesta Key lifestyle. Recent upgrades include new AC system. This unit has a Strong rental history.

6310 Midnight Pass Road Unit 403N, Sarasota
1260 Dolphin Bay Way Unit 203, Sarasota
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Discover the relaxed elegance of waterfront living at Dolphin Bay, one of Siesta Key’s desirable gated condominium communities. Enjoy beautiful views of Sarasota Bay from this spacious two-bedroom, two-bath residence offering 1,915 square feet of thoughtfully designed living space, complemented by multiple outdoor areas that invite you to embrace the coastal lifestyle. Bright, welcoming interiors feature an expansive living and dining area, a separate family room, and a beautifully refreshed kitchen with white quartz countertops, freshly painted cabinetry and an inviting breakfast bar. A unique and thoughtful feature is the remote-controlled privacy screen that separates the family room from the kitchen, creating a comfortable, temporary guest retreat when needed. This versatile space offers added flexibility for visiting family and friends while preserving the home's open, inviting design. Hard-surface flooring flows throughout, while the split-bedroom floor plan provides privacy and comfort, with both bedrooms featuring en-suite baths. The generous covered rear lanai extends the living space outdoors, offering peaceful views of the tropical grounds and sparkling bay beyond. A covered front terrace and additional sunning deck provide even more opportunities to enjoy Siesta Key's beautiful weather. Additional highlights include a private one-car garage beneath the building, ample guest parking, and a new HVAC system and water heater installed in 2024. Dolphin Bay offers an exceptional combination of waterfront beauty and resort-style amenities, including a clubhouse, swimming pool, spa, tennis courts, fitness center and day dock. This gated, pet-friendly community enjoys a convenient location near Siesta Key's celebrated beaches, with the island trolley just outside the entrance connecting you to the restaurants, shopping and entertainment of Siesta Village. Whether enjoying a quiet morning overlooking the water, entertaining friends or spending the afternoon at the beach, this inviting residence captures the comfort, versatility and effortless enjoyment of the Siesta Key lifestyle.

1260 Dolphin Bay Way Unit 203, Sarasota
304 Calle Miramar Unit 304S, Sarasota
$2,495,000
4 Beds ⋅ 4 Baths ⋅ Beach Villas At The Oasis SubDv. ⋅ 34242 Zip Code
Experience exceptional Siesta Key living in this distinctive two-level penthouse, crowned by an expansive private rooftop terrace with Gulf glimpses, spectacular sunsets and refreshing coastal breezes. Ideally situated in the heart of Siesta Village, just a short stroll from the world-renowned sands of Siesta Beach, this turnkey furnished residence offers 3,236 square feet of beautifully appointed living space, four bedrooms, four baths and multiple private outdoor terraces. The rooftop terrace is a true highlight, creating an extraordinary setting for sunset gatherings, entertaining under the stars or simply relaxing above the vibrant Village atmosphere. Inside, spacious open-concept living areas are designed for comfort and entertaining, complemented by a well-appointed kitchen with a generous center island, breakfast bar and seamless access to outdoor terraces. A separate entertainment room features a wet bar and expansive terrace, providing additional space for family and guests. The inviting primary suite offers a private terrace and spacious bath with soaking tub and walk-in shower, while a second en-suite bedroom and two additional guest bedrooms provide comfortable accommodations. A private elevator connects the oversized attached two-car garage to the living levels, offering convenience and ample storage for beach and recreational gear. Within an intimate, gated community of just 12 residences in three four-unit buildings, each building enjoys its heated pool and spa. Offered turnkey furnished for immediate enjoyment, this exceptional penthouse places the boutiques, restaurants and lively atmosphere of Siesta Village nearby, with Siesta Beach an easy distance from home. Whether enjoyed as a full-time residence, luxurious island retreat or vacation property with rental potential, subject to community restrictions, this remarkable offering combines generous living spaces, exceptional outdoor retreats and one of Siesta Key's desirable locations.

304 Calle Miramar Unit 304S, Sarasota
1260 Dolphin Bay Way Unit 301, Sarasota
$1,750,000
3 Beds ⋅ 3 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Experience refined waterfront living at Dolphin Bay, an intimate, pet-friendly community of just 50 residences on Siesta Key. Beautifully redesigned with a sophisticated coastal aesthetic, this exceptional three-bedroom, three-bath condominium offers nearly 2,500 square feet of beautifully appointed living space and captivating views of the Intracoastal Waterway. Bright, open interiors create an effortless sense of space, with 9-foot ceilings, elegant plank tile flooring, custom built-ins and beautifully updated baths. At the heart of the residence, an impressive chef's kitchen makes a striking statement with expansive countertops, generous gathering spaces, custom cabinetry and premium Sub-Zero, Monogram and Viking appliances. A dramatic six-foot, built-in double-door wine cellar adds a distinctive touch for entertaining. The spacious living and dining areas flow beautifully toward the waterfront, where walls of glass frame the Intracoastal views. An expansive, air-conditioned enclosed lanai extends the living space, creating an inviting year-round retreat for relaxing, entertaining or simply watching the boats pass by. Thoughtful details include custom cabinetry, recessed lighting and integrated theater speakers. The generously sized bedrooms and spa-inspired baths offer comfort and privacy for family and guests. Recent improvements include impact-resistant windows and sliding doors installed in 2025, along with custom motorized light-filtering and room-darkening shades. Additional updates include the HVAC system (2020) and water heater (2021). A private one-car garage beneath the building adds convenience and additional storage. Residents of Dolphin Bay enjoy an inviting coastal lifestyle with a beautifully updated clubhouse, fitness center, Har-Tru tennis courts, heated pool and spa, and a day dock for boating and fishing. Siesta Key's world-renowned white-sand beaches and the restaurants, boutiques, and entertainment of Siesta Village are just minutes away, with convenient trolley access. Combining beautifully curated interiors, remarkable waterfront views and easy elegance of island living, this is an exceptional opportunity to enjoy Siesta Key at its finest.

1260 Dolphin Bay Way Unit 301, Sarasota
5950 Midnight Pass Road Unit 101, Sarasota
$485,999
1 Beds ⋅ 1 Baths ⋅ Siesta Beach House SubDv. ⋅ 34242 Zip Code
An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Built a solid foundation of bookings into February and March bookings. Repeat Guests and higher demand! Located within Siesta Beach House this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.

5950 Midnight Pass Road Unit 101, Sarasota
1313 Dockside Place Unit 120, Sarasota
$1,090,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
RARE BOATER’S OPPORTUNITY! 45' BOAT SLIP with NEW 27,000-lb IMM/Quality Platinum Series boat lift on deep, sailboat water! Completely renovated waterfront townhouse-style residence with the slip directly behind the unit—a highly desirable and rarely available location. Ultimate Beach lifestyle with easy access to Siesta #1 Beach & Siesta Village, just a few minutes' walk away. Enjoy mornings on the beach, afternoons on the boat, and evenings sunsets & exploring the Village. With many restaurants, music & shops. Fully remodeled down to the block walls with new plumbing, electrical, HVAC and ductwork, drywall, raised ceilings, LED lighting, and beautiful wood-look porcelain tile throughout. Gourmet kitchen features custom cabinetry, GE Profile appliances, natural quartzite, and abundant storage. Both baths offer easy-entry showers, and the primary suite includes a walk-in closet with custom organization. Private one-car garage, additional parking, attic storage, and newly screened lanai for entertaining. Elevated to 11.5' floor level remained free of stormwater during the 2024 storms. The dock features new pilings, full-length finger pier, fresh water, 30-amp/120V service, remote-controlled lift with auto-stop, and approximately 7' of water depth. Protected harbor approximately 100 yards from the ICW and just 10 minutes to Sarasota Big Pass. HOA permits boats up to 45' feet. Complex is getting a look and remodel! See photos Beach. Boating. Village life. All from one exceptional Siesta Key location. Community is going through a major face lift!! Scope of renovations • Siding/Trim/Facia with Stain-paint • Railings • Stairs • Gutter/Downspouts • Lighting

1313 Dockside Place Unit 120, Sarasota
5300 Ocean Boulevard Unit 301, Sarasota
$1,195,000
2 Beds ⋅ 2 Baths ⋅ Terrace East SubDv. ⋅ 34242 Zip Code
RELISTED WITH AN ALMOST $200,000 PRICE ADJUSTMENT. This unique beach condo with sunrise, sunset and 270-degree views is an excellent opportunity. A beachy 1,446 square-foot, 2-bedroom 2-bath corner residence with extra space for a den boasts a special sunny, oversized corner, south-facing wraparound balcony with views of the beach, Gulf of Mexico, heated pool and Siesta Village. The unusual 1,130 square foot terrace adds extra space and is very useful for romantic alfresco dining, entertaining family and friends, special parties, kid's play space, put-put golf, shuffleboard, Florida sunning and more, which is not available in other condos. From this incredible Siesta Key location, you just walk out to the sugar-white sands of #1 Siesta Key beach for a relaxing swim in the azure-blue Gulf of Mexico or get some exercise walking the 3 miles of beachfront, snorkel, paddleboard, or take your beach bike for a spin on the beach. Enjoy your morning coffee or a cocktail from your extensive terrace balconies while watching the colorful hues of the Florida sunrise and sunset without having to leave your condo. For an entertaining experience, you are steps from quaint Siesta Village to indulge in fun shopping, dining and live music. The floor plan flows from the balcony on the beachside through to the back of the building with views looking east over Siesta Village and west over the Gulf of Mexico. This delightful light & bright larger corner residence features tile throughout perfect for beach living, a covered parking space and is just waiting for your personal touch. The elevator serves only two condos per floor with an updated private foyer and private laundry facilities shared by two condos. Private & exclusive Terrace East has a modern updated lobby and social room, newly refinished pool with new grills & refrigerator, new pool furniture, new roof in 2025, and equipped fitness center. All the fixed windows in all the condos will be replaced by the association by January 2028. This is a secure gated building with onsite full-time manager and maintenance man, very well-run association with active board and no current special assessments, and a secure surveillance system. Amenities include a heated pool for laps, a tennis court, pickleball, active fitness center, beautifully landscaped garden and grounds, and bicycle & paddleboard storage. Come make this your future Florida home!

5300 Ocean Boulevard Unit 301, Sarasota
6204 Midnight Pass Road Unit 205, Sarasota
$775,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Welcome to Siesta Dunes! This bright and airy second-floor end-unit condominium offers a wonderful combination of comfort, updates, and location, with peaceful garden views and a peek-a-boo view of the Gulf. High ceilings and an abundance of natural light create a spacious, open feel throughout the residence, while new hurricane-impact windows provide added peace of mind. The roof and air conditioning system are also newer. The two bed, two bath layout features an updated kitchen with ample counter space and a convenient dinette area. The spacious living room opens through sliding glass doors to the balcony, extending the living space outdoors and providing a pleasant spot to enjoy the surrounding views. The primary suite offers a walk-in closet and ensuite bath, while the additional guest bedroom and full bath provide comfortable accommodations for family and friends. The desirable gulf front community of Siesta Dunes offers a saltwater pool & spa, tennis and pickleball courts, a beach deck and pavilion, carports, additional storage and small pets are allowed. Weekly rentals are also permitted, making this an appealing opportunity for those looking for a vacation home with rental potential or an investment property. With easy access to the renown Siesta Key Village, where you can enjoy the tropical ambiance of dining, shopping, and entertainment as well as everything Sarasota has to offer including the arts and culture of downtown. Whether you're looking for a place to enjoy yourself or an opportunity to generate rental income, this Siesta Dunes residence offers the flexibility, updates, and location to enjoy the best of the Florida lifestyle.

6204 Midnight Pass Road Unit 205, Sarasota
420 Beach Road Unit 507, Sarasota
$1,695,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Siesta Key Beach paradise! Wake up to Gulf breezes and end each day with a sunset on the beach from this direct beachfront condo at Siesta Gulf View. This fifth floor center unit 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened balcony, accessible from the living room, kitchen, and primary suite. This beautifully updated unit with open floor plan, newly installed 2026 air conditioner with coastal coil, reverse osmosis both refrigerator water/ice, full granite counter tops, all stainless steel appliances, shaker cabinets throughout and beach decor with Restoration hardware custom leather sectional. Primary bedroom has his/her walk in closets and built-in linen closet. This income producing TURNKEY FURNISHED with Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping., with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate Beach resort living this is a MUST SEE! Land, Site, and Tax Information

420 Beach Road Unit 507, Sarasota
1229 Moonmist Circle Unit P6, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Polynesian Gardens SubDv. ⋅ 34242 Zip Code
TURNKEY FURNISHED, FREE-STANDING VILLA ON SIESTA KEY! TAKE YOUR GOLF CART TO PUBLIC BEACH! Ideally located in the highly desirable Polynesian Gardens along the Intracoastal Waterway, this charming 2-bedroom, 2-bath villa offers the privacy and feel of a single-family home with the convenience of low-maintenance, lock-and-leave living. TWO DOGS ALLOWED! LOW HOA FEES. An excellent choice for a personal island retreat. One of only ten villas overlooking the expansive community pool, this home features a private entrance, covered carport, screened lanai, and inviting outdoor living spaces surrounded by lush tropical landscaping. Relax around the LP gas fire pit or enjoy the Florida sunshine just steps from the community pool. The villa is also positioned at one of the higher elevations within the community. Major updates include a NEW ROOF (2023), HVAC SYSTEM (2023), WATER HEATER (2025), NEW GUTTERS (2025), programmable Nest thermostat, remote-entry touch keypad lock, and remote camera system. (OVER $100,000 OF RENOVATIONS HAVE BEEN DONE.) Enjoy everything the Siesta Key lifestyle has to offer! Spend your days fishing or watching dolphins and manatees from the community dock and fishing pier overlooking the Intracoastal Waterway. Walk or take your GOLF CART to nearby dining, shopping, coffee shops, nightlife, grocery stores, marina access, and local favorites including Captain Curt’s. World-famous Siesta Key Beach, known for its powdery white quartz sand, is just across the street. Hop aboard the free trolley to Siesta Key Village for even more dining, shopping, and entertainment. Rental history is available in the attachments. Whether you’re looking for your own island getaway, a seasonal rental, or an easy-care Florida retreat, this villa offers an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle. MOVE IN, RENT OUT, OR SIMPLY RELAX!

1229 Moonmist Circle Unit P6, Sarasota
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