Siesta Key Homes with Pool Community Features

Siesta Key Homes with Pool Community Features

Welcome to Siesta Key, Florida, a picturesque island paradise nestled in Sarasota County. Renowned for its pristine beaches, Siesta Key boasts powdery white sands and crystal-clear turquoise waters, making it a top destination for sun-seekers and nature lovers alike. The island's vibrant atmosphere is complemented by charming boutiques, delightful dining options, and a rich array of outdoor activities, from kayaking and paddleboarding to biking along scenic trails.

Siesta Key is not just a vacation hotspot; it’s a thriving community where residents enjoy a laid-back lifestyle infused with coastal charm. The real estate market here offers an impressive selection of homes, many of which feature luxurious pools. Imagine stepping into your own backyard oasis, where you can unwind under the Florida sun, host lively barbecues, or simply take a refreshing dip after a day at the beach.

The homes in Siesta Key are as diverse as its residents, ranging from cozy beach cottages to stunning waterfront estates. Many properties come with community features that enhance the living experience, such as private pools, clubhouses, and access to recreational facilities. Whether you’re looking for a family-friendly neighborhood or a serene retreat, Siesta Key has something to offer everyone.

With its unique blend of natural beauty, vibrant culture, and welcoming community, Siesta Key is more than just a place to live; it’s a lifestyle waiting to be embraced. Explore the possibilities of making this coastal gem your home, where every day feels like a vacation.

Newest Siesta Key Homes with Pool Community Features

2 Beds ⋅ 3 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code

Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create an extraordinary 2,365-SF home. Completely reimagined by award-winning architect Michael Halflants of Halflants + Pichette Studio for Modern Architecture, the residence received the prestigious AIA Florida/Caribbean Honor Award of Excellence in Interior Design and was featured in Sarasota Magazine's Dream Homes issue. Original interior walls were removed to reveal uninterrupted vistas that extend along the shoreline of Siesta Key, across Sarasota Bay, and to the downtown Sarasota skyline. The result is a flowing two-bedroom, two-and-a-half-bath residence where panoramic views, exceptional materials, and thoughtful design exist in perfect balance. At the center of the home, a sculptural Etimoe hardwood core houses the kitchen, storage, primary bath, and an expansive walk-in closet, bringing warmth and architectural definition to the open floor plan. Floor-to-ceiling, seven-panel bi-fold glass doors disappear completely at the corners, creating a seamless connection to the Gulf and inviting coastal breezes into the living spaces. Custom folding partitions provide privacy between the primary suite and main living areas without compromising the home's openness or visual continuity. Thoughtful custom details continue throughout the residence, including a custom steel desk overlooking the Gulf of Mexico, creating a work-from-home setting few could rival. The raw concrete ceiling from Smith's original 1969 design was scraped and clear-coated to a soft sheen, transforming a defining element of the building into a striking contemporary feature. Large-format porcelain tile, custom steel detailing, and carefully selected wood finishes complete a sophisticated material palette that feels both timeless and contemporary. Residents of The Terrace enjoy private access to Siesta Key's renowned beach and are just moments from the shops, restaurants, and energy of Siesta Village. More than a luxury beachfront residence, this is a rare opportunity to own an award-winning home within one of Sarasota's most recognizable waterfront landmarks, where exceptional architecture and Gulf-front living are seamlessly intertwined.

5400 Ocean Boulevard Unit #15 1-4, Sarasota

2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

Opportunities to own in Sandy Cove are rare—and this residence presents the perfect chance to create your own island retreat in one of Siesta Key's most sought-after waterfront communities. Bring your vision and transform this well-located residence into the coastal getaway you've always imagined. Whether you're looking for a winter escape from the cold, a seasonal home to enjoy for years to come, or an investment in one of Florida's premier beach destinations, the value here lies in the location, lifestyle, and potential. Designed by renowned Sarasota architect Frank Folsom Smith, Sandy Cove is a boutique waterfront community celebrated for its timeless mid-century architecture, lush tropical landscaping, private shell beach, fishing pier, heated pool, kayak launch, and Gulf-front sunsets. Best of all, you're just a short stroll from Siesta Key Village, where local restaurants, boutiques, live music, and island charm await. Unlike buying someone else's renovation, this home offers the rare opportunity to update the interior to reflect your own style while investing in a community where demand remains consistently strong. Enjoy the property today, renovate at your own pace, and own a piece of Siesta Key in a location that continues to attract vacationers, seasonal residents, and investors alike. When the address is this exceptional, the possibilities are endless. Schedule your private showing today!

220 Pass Key Road Unit 220, Sarasota

2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code

Welcome to your Siesta Key beach retreat! Perfectly positioned directly across from world-famous Siesta Key Beach, this immaculate, beautifully renovated 2-bedroom, 2-bath condominium offers the ideal combination of coastal luxury and exceptional investment potential. Completely renovated in 2019, this turnkey residence features recently installed hurricane-impact windows and sliding glass doors, a beautifully updated kitchen with stone countertops and stainless-steel appliances, a remodeled master suite, updated bathrooms, all-new PVC plumbing throughout, in-unit laundry, and a bright, open floor plan designed for easy beach living. Relax on your private lanai overlooking the tranquil lake or take a short walk to the powder-soft sands and crystal-clear waters of Siesta Key Beach. A rare attached private garage with epoxy floors provides additional convenience and storage. Residents and guests enjoy outstanding community amenities, including a pavilion with grills, an outdoor shower, a heated pool, tennis and pickleball courts, and beautifully maintained tropical grounds. Investors will appreciate the short-term rental flexibility, with both on-site professional property management and self-management options available, allowing owners to maximize rental income while maintaining complete flexibility. Whether you’re searching for a full-time residence, vacation getaway, or income-producing property, this condominium checks every box. Most furnishings are negotiable, offering the opportunity to purchase a fully furnished, turnkey property and begin enjoying or renting it immediately. Located just minutes from Siesta Key Village’s popular restaurants, boutique shopping, and entertainment, this is a rare opportunity to own a move-in-ready property in one of Florida’s most sought-after beach communities.

1135 Lake House Circle Unit C115, Sarasota

2 Beds ⋅ 2 Baths ⋅ House Of The Sun (Was Known As Haleakala) SubDv. ⋅ 34242 Zip Code

The best Gulf views currently available at House of the Sun! This rarely available third-floor residence is ideally positioned on the south side of the building, offering sweeping Gulf views and an exceptional beachfront lifestyle on Siesta Key. Enjoy breathtaking sunsets from the living room and private lanai, with world-famous Siesta Beach just steps from your door. House of the Sun features 100 feet of direct beachfront and an unbeatable location just 500 feet south of the Stickney Point Bridge, providing convenient access to the mainland while remaining within very short distance of restaurants, entertainment, coffee shops, gourmet markets, boutiques, salons, postal services, and beach, sport, and boat rentals. Local favorites including Captain Curt's and Daiquiri Deck are just around the corner. The residence has been thoughtfully updated with hurricane-impact windows, a newer A/C system, fresh interior paint, and beautiful stone-look porcelain tile flooring throughout the living areas, kitchen, and bedrooms. The kitchen features stainless steel appliances, granite countertops, and a stylish backsplash. Both bathrooms have been completely renovated with marble flooring, granite vanities, new sinks, and updated finishes. Additional highlights include a newer in-unit washer and dryer, owner's storage closet, and under-building assigned parking. House of the Sun has recently completed extensive property enhancements (2024-2025), including new elevators, a new roof, renovated pool and tennis court, an updated poolside clubhouse with new fitness equipment, new gas grilling stations, refreshed outdoor seating areas, upgraded landscaping, newly painted hallways, new carpeting and lighting, and enhanced building-wide Wi-Fi. Pet-friendly for owners, House of the Sun is also recognized for one of Siesta Key's premier on-site rental programs, featuring a three-night minimum rental policy. This residence has a strong rental history, making it an outstanding opportunity for both personal enjoyment and income potential. Sale is subject to existing future rental bookings.

6518 Midnight Pass Road Unit 309, Siesta Key

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

3 Beds ⋅ 4 Baths ⋅ Sunset Beach SubDv. ⋅ 34242 Zip Code

Introducing Residence #304 at Sunset Beach, Siesta Key's newest luxury address, where sophisticated coastal design and effortless living come together in an exclusive boutique beachfront community. One of only 11 private residences, this beautifully appointed home offers an exceptional blend of spacious interiors, elevated finishes, and timeless modern elegance. Designed to maximize comfort and functionality, the open-concept floor plan is filled with natural light through floor-to-ceiling hurricane-impact glass that seamlessly connects the living spaces to expansive outdoor terraces. The chef's kitchen is thoughtfully crafted with custom cabinetry, premium Wolf and Sub-Zero appliances, and designer finishes, while the spacious great room creates the perfect setting for entertaining or simply unwinding after a day on the beach. Luxurious bedroom suites provide a private retreat, each designed with comfort and sophistication in mind. Situated on 2.5 Gulf-front acres with 175 feet of private beachfront, Sunset Beach offers an unmatched collection of resort-style amenities, including a beachfront pool and spa, private cabanas, a fire pit, fitness center, grilling area, bicycles, and private owner storage. Just a short walk from Siesta Key Village, you'll enjoy boutique shopping, acclaimed restaurants, coffee shops, and live entertainment while returning home to the privacy and exclusivity of one of the island's most coveted new communities. Residence #304 offers the perfect combination of luxury, location, and exceptional design, making it an extraordinary opportunity to own at Siesta Key's newest luxury address.

70 Avenida Veneccia Unit 304, Sarasota

4 Beds ⋅ 4 Baths ⋅ Sunset Beach SubDv. ⋅ 34242 Zip Code

Introducing Residence #201 at Sunset Beach—the corner model residence at Siesta Key's newest luxury address. This professionally designed showcase home offers breathtaking Gulf views, abundant natural light, and an exceptional blend of modern coastal elegance, all within an exclusive collection of just 11 beachfront residences. Designed for both everyday living and effortless entertaining, the residence features an open-concept floor plan with floor-to-ceiling hurricane-impact glass that seamlessly connects the interior to expansive Gulf-front terraces. Every detail has been thoughtfully curated with high-end designer finishes, a custom chef's kitchen featuring Wolf and Sub-Zero appliances, and a private bar in the living area—perfect for hosting family and friends. Situated on 2.5 Gulf-front acres with 175 feet of private beach, Sunset Beach offers resort-style amenities including a beachfront pool and spa, cabanas, fire pit, fitness center, grilling area, bicycles, and private owner storage. Ideally located, you'll enjoy the privacy of a boutique beachfront community while being just a short walk to Siesta Key Village, where charming boutiques, waterfront dining, coffee shops, and live entertainment await. Experience refined beachfront living at one of Siesta Key's most exclusive new communities. Contact us today to schedule your private tour of Residence #201.

70 Avenida Veneccia Unit 201, Sarasota

4 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code

Fractional Ownership. Experience luxury beachfront living on Siesta Key through this exceptional 1/16th fractional ownership opportunity at Hyatt Vacation Club. This desirable summer ownership package includes two consecutive fixed weeks—Weeks 32 and 33—plus one additional floating week each year, subject to availability and Hyatt Vacation Club’s reservation guidelines. A 1/16th ownership interest allows you to enjoy the benefits of owning a professionally managed luxury residence without the expense, maintenance, or responsibilities associated with full-time ownership. In addition to your guaranteed fixed summer weeks on Siesta Key, the floating week offers added flexibility for another annual stay. Owners may also have opportunities to use their Hyatt Vacation Club ownership to explore other participating Hyatt Vacation Club properties, subject to Hyatt Vacation Club’s applicable exchange program, reservation procedures, point values, and availability. Set directly on the Gulf of Mexico, this expansive Siesta Key beachfront residence offers the space, comfort, and privacy of a luxury condominium combined with the services and amenities of a premier resort. The thoughtfully designed floor plan includes a spacious primary suite, a junior suite, a guest bedroom, and a den with a sleeper sofa, providing comfortable accommodations for family and guests. The residence is beautifully appointed with custom furnishings originally valued at more than $150,000, imported linens, and a fully equipped gourmet kitchen featuring premium appliances by Wolf, Sub-Zero, and Fisher & Paykel. Every detail has been carefully considered, allowing owners to arrive, settle in, and immediately begin enjoying their Siesta Key vacation. Ownership also includes access to Hyatt Vacation Club’s renowned hospitality services, including attentive front-desk and recreation staff, assistance with local activities and reservations, valet parking, and 24-hour security. Owners enjoy the lifestyle of a luxury Gulf-front condominium with resort-style services and amenities—at a fraction of the cost of purchasing and maintaining a full-time beachfront residence. This is a rare opportunity to own a summer fractional package on Siesta Key Beach, enjoy two consecutive fixed weeks each year, benefit from an additional floating week, and potentially experience other Hyatt Vacation Club destinations through the ownership program.

915 Seaside Drive Unit 613, Weeks 32-33, Sarasota

2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code

Discover this one-of-a-kind unit in Excelsior, featuring two spacious bedrooms and two bathrooms, complemented by an added staircase leading to a spacious second-story LOFT. A structural beam has been expertly installed to support the loft, and all ceilings have been RAISED, enhanced with foam insulation throughout the attic for improved energy efficiency. The kitchen boasts custom solid wood cabinetry, elegant crown molding, and solid core doors. BRAND NEW carpet installed throughout bedrooms, loft and staircase. Enjoy year-round comfort with a Newer HVAC system (2023). Looking out from your front door, take in the breathtaking Gulf views, perfect for watching gorgeous sunsets. The Gulf to Bay community offers private deeded beach access and a wealth of amenities, including two large heated swimming pools with poolside restrooms and hot water showers, shuffleboard, two heated whirlpools, two lighted tennis courts, and two pickleball courts. For fitness enthusiasts, a well-equipped fitness center awaits, along with a spacious Gulf side sun deck, beach loungers and chairs, and outdoor barbecues and picnic areas. 2 Week rental minimums for those seeking to generate some income. Additionally, enjoy the intercoastal fishing pier with a shaded viewing area, a welcoming community room, and engaging monthly community events. Don’t miss your opportunity to own this exceptional property with unparalleled amenities!

6263 Midnight Pass Road Unit 403, Sarasota

2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code

Welcome to Jamaica Royale #93, a beautifully remodeled two-bedroom, two-bath garden-view condominium nestled within the lush tropical grounds of Jamaica Royale on world-renowned Siesta Key. Offering 921 square feet of thoughtfully updated living space, this inviting coastal retreat showcases a complete 2025 renovation with quality finishes throughout, creating the perfect blend of modern comfort and relaxed coastal style. The stunning new kitchen features custom cabinetry, elegant quartz countertops, a ceramic tile backsplash, new stainless steel appliances, and a new garbage disposal. Additional 2025 improvements include new HVAC systems (inside and out), a new hot water heater, fresh interior paint, stylish new furnishings, hurricane impact-resistant windows and sliding glass doors, luxury vinyl plank flooring in both bathrooms, new bathroom vanities and fixtures, and beautifully remodeled showers with ceramic tile surrounds, frameless glass doors, and contemporary finishes. The spacious primary suite features a king-size bed, while the guest bedroom offers two queen-size beds, providing ample space for family and guests. Step outside to your private patio with comfortable outdoor seating—the perfect place to enjoy your morning coffee, dine al fresco, or relax after a day on the beach. Located just steps from the world-famous powdery quartz sands and turquoise waters of Siesta Key Beach, owners and guests enjoy deeded beach access and an exceptional array of resort-style amenities, including three heated community pools, shuffleboard courts, community grilling areas, beautifully landscaped tropical grounds, and one assigned parking space. Public transportation conveniently stops directly in front of the community, providing easy access to Siesta Key Village's restaurants, boutiques, entertainment, and vibrant island nightlife. Whether you're searching for a private beach retreat, seasonal residence, or an outstanding investment opportunity with excellent rental potential, Jamaica Royale #93 offers a truly turnkey opportunity in one of Siesta Key's most desirable beachfront communities!

5830 Midnight Pass Road Unit 93, Sarasota

1 Beds ⋅ 2 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code

Turnkey furnished and beautifully reimagined in 2024, this top-floor Gulf-front residence at Fisherman's Cove offers a rare opportunity to own one of Siesta Key's most distinctive beachfront retreats. Positioned at the quiet southern end of the island, this one-bedroom residence enjoys unobstructed panoramic views of the Gulf of Mexico from nearly every room, where turquoise waters, sugar-white sand, and breathtaking sunsets become part of everyday living. Thoughtfully renovated throughout, this residence is also the only one-bedroom floor plan in the community offering both a full bath and an additional half bath, providing added comfort and convenience for guests. Designed to maximize natural light and waterfront scenery, the open floor plan flows effortlessly from room to room. The Gulf-front terrace has been enclosed, expanding the living space while walls of impact-rated glass frame uninterrupted beach views. Soft coastal finishes, elegant tile flooring, and a fresh, contemporary palette create a relaxed yet refined atmosphere ideal for full-time living, seasonal enjoyment, or investment. The remodeled kitchen features custom cabinetry, stone countertops, newer appliances, generous storage, and an open design that overlooks the living and dining areas while keeping the Gulf as the focal point. Renovations completed in 2024 include impact windows and sliding glass doors, beautifully updated bathrooms, and quality finishes throughout, while a newer air-conditioning system installed in 2023 adds peace of mind. The spacious primary suite enjoys spectacular Gulf views through oversized windows and features an updated en-suite bath. The additional powder room is a rare feature within Fisherman's Cove, allowing guests the convenience of a separate bath while maintaining the privacy of the primary suite. Nestled between the Gulf of Mexico and Blind Pass Lagoon, Fisherman's Cove offers one of Siesta Key's most desirable waterfront settings. Residents enjoy direct beach access, a heated community pool, fishing pier, complimentary first-come boat slips, and easy access to kayaking, paddleboarding, and boating that leads to Sarasota Bay and the Gulf. The island's south end is also renowned for exceptional shelling and miles of unspoiled shoreline stretching toward Casey Key. Ideally located just minutes from Siesta Key Village, waterfront dining, marinas, and downtown Sarasota's renowned Cultural Coast, residents enjoy boutique shopping, acclaimed restaurants, theaters, galleries, Selby Gardens, and year-round entertainment. Whether you're searching for a luxurious beachfront escape, a high-demand investment with one-week rental flexibility, or a move-in-ready Gulf-front residence, this exceptional Fisherman's Cove offering delivers the very best of Siesta Key living.

9000 Blind Pass Road Unit 303, Sarasota

2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code

ATTENTION INVESTORS, VALUE MINDED BUYERS AND HOMEOWNERS!, one of the best value for a 2 bedroom 2 bath villa currently on beautiful Siesta Key. Discover effortless island living in this beautifully updated, TURNKEY FURNISHED , maintenance-free villa on Siesta Key. Offering two bedrooms and two full baths plus its OWN CARPORT, this renovated residence is ideally located just a very short distance from the world-famous sugary sands of Crescent Beach on beautiful Siesta Key. The stylish kitchen has been refreshed with brand new appliances, and contemporary designed cabinets that is both functional and inviting. Recent upgrades also include a new HVAC system and water heater, providing year-round comfort and peace of mind. Luxury vinyl plank flooring in all bedrooms and tile throughout the unit for that extra "Clean feel", creating a cohesive look while offering lasting durability and easy maintenance. Storm windows and energy efficient throughout ( except the sliders). WASHER AND DRYER INCLUDED! Unwind in the private screened lanai, ideal setting to enjoy the gentle Gulf breezes any time of day, enhanced with an extra storage closet for all the beach toys, not to mention a laundry closet with brand new washer and dryer to boot . Both bathrooms have been tastefully remodeled with modern finishes, completing the home's move-in-ready appeal. HOA also includes water and internet service and flood insurance. The villa is conveniently situated just steps from the community clubhouse, swimming pool, outdoor grilling area. Enjoy the convenience of nearby boutiques, restaurants, and local entertainment, all within very short distance. The complimentary Siesta Key trolley provides easy transportation to Siesta Key Village, where you'll find additional shopping, dining, and vibrant island attractions. Whether you're searching for a seasonal getaway, an income-producing investment property, or a full-time coastal residence, this exceptional villa offers the perfect opportunity to experience the relaxed Siesta Key lifestyle. Schedule your private showing today and discover everything this island paradise has in store for you.

159 Vista Hermosa Circle Unit 27B, Sarasota

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