Sarasota/Crescent Beach/Siesta Key Homes with Pool Community Features

Sarasota/Crescent Beach/Siesta Key Homes with Pool Community Features

Welcome to the enchanting paradise of Sarasota, where the sun-kissed shores of Crescent Beach and Siesta Key beckon with their pristine beauty. Nestled along Florida’s Gulf Coast, this region is renowned for its powdery white sand beaches, vibrant culture, and a lifestyle that seamlessly blends relaxation with recreation.

Crescent Beach, a hidden gem, offers a tranquil escape with its serene atmosphere and stunning views of the azure waters. Just a stone's throw away, Siesta Key boasts a lively community, filled with charming boutiques, delightful eateries, and an array of water sports that cater to every adventurer's spirit. Whether you’re strolling along the beach at sunset or indulging in fresh seafood at a local restaurant, the allure of Siesta Key is undeniable.

For those seeking a home that embodies the essence of this coastal paradise, the Homes with Pool community features are a perfect match. Imagine waking up to the gentle sound of waves and stepping out to your own private oasis. These homes not only provide luxurious swimming pools ideal for cooling off on warm Florida days but also offer spacious outdoor living areas, perfect for entertaining friends and family or simply enjoying a quiet evening under the stars.

With a strong sense of community and a plethora of activities, Sarasota, Crescent Beach, and Siesta Key present an idyllic lifestyle. Whether you are looking for a vacation home or a permanent residence, this region promises a blend of comfort, luxury, and the unmatched beauty of Florida’s coastline. Come experience the magic of Sarasota and discover your dream home today!

Newest Sarasota/Crescent Beach/Siesta Key Homes with Pool Community Features

6154 Midnight Pass Road Unit A-3, Sarasota
$579,000
2 Beds ⋅ 2 Baths ⋅ Casa Blanca Villas SubDv. ⋅ 34242 Zip Code
The day starts with bare feet on cool terrazzo and a short walk to the beach, where the sugar-white quartz sand of Crescent Beach is already warming in the sun. You might take a shelling stroll toward Point of Rocks, swim in the Gulf, or simply settle into a beach chair. By late morning you are back at your own freestanding villa, rinsing off the sand and pouring something cold on the screened porch while the breeze moves through the palms. This furnished 2-bedroom, 1.5-bath villa in the beachfront community of Casa Blanca is ready the moment you arrive. The renovated kitchen has stainless appliances and room to eat in, the bathrooms are refreshed, and an impact-rated sliding glass door opens to the porch. There is a rare in-unit laundry, so beach towels never wait for a trip across the grounds. This is 1-story living with parking right at your front door. Afternoons belong to the heated community pool and clubhouse, just steps away. In the evening, the trolley takes you to the restaurants and shops of Siesta Key Village, or you can stay close to home and walk back to the beach for sunset. When you are away, Casa Blanca's on-site rental management and flexible 5-7 day minimum rentals let the villa earn seasonal income while you reserve the weeks you want for family and friends. Whether it becomes your personal beach retreat, an investment, or both, this is the Siesta Key story, waiting for its next chapter.

6154 Midnight Pass Road Unit A-3, Sarasota
6312 Midnight Pass Road Unit 305S, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code
Picture your mornings starting with coffee on your screened lanai, a gulf view and soft sea breezes, then a few steps to the powdery white sand of world-famous Siesta Key beach. This 2-bedroom, 2-bath beachfront condo in a waterfront gated community is your own seasonal getaway when you want it and an established vacation rental when you don't. Weekly rentals are permitted, and the residence is already an active vacation rental with a proven booking history, so it can help offset the cost of ownership while you are away. Sold furnished and turnkey, it is ready to enjoy from the day you close. A split bedroom plan places a private en-suite bath with each bedroom, so guests and family each have their own retreat. Tile flooring throughout and a bright white kitchen with stainless appliances make for easy, low-maintenance coastal living. A large storage closet holds beach chairs, umbrellas and toys, and beach chairs are provided on the sand for owners and guests. Crescent Arms offers direct beach access, a community pool, tennis, an elevator and an assigned carport space, with a water view from the grounds and the Gulf just steps away. Stroll to nearby restaurants and shops, or hop on the free Siesta Key trolley to explore the island. A rare chance to own a piece of Siesta Key that works for you whether you are here or not.

6312 Midnight Pass Road Unit 305S, Sarasota
5855 Midnight Pass Road Unit 611, Sarasota
$599,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
PRICED TO SELL! Walk into over $20,000 rental income! Discover the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, where waterfront surroundings, resort-style amenities, and rental flexibility come together. Located on the sixth floor, this two-bedroom, two-bath condominium is being sold TURNKEY FURNISHED and has partial views of the Intracoastal Waterway—a relaxing backdrop for watching the boats go by. Whether you’re seeking a full-time residence, seasonal retreat, or investment property, this condo offers an appealing opportunity to own on one of Florida’s most beloved barrier islands. The building has undergone an extensive renovation, including all-new hurricane-impact windows and doors, adding to the appeal of this established waterfront community. A two-week minimum rental policy provides flexibility to enjoy your own island getaways while pursuing vacation-rental income when you’re away. Private storage locker included.

5855 Midnight Pass Road Unit 611, Sarasota
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 on the waterfront facing side, 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
5830 Midnight Pass Road Unit 38, Sarasota
$540,000
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Beautifully renovated in 2025, turnkey furnished, and a short distance from the powder-white sands of Siesta Key Beach! Discover an exceptional opportunity to own a virtually new coastal retreat in Jamaica Royale, a highly desirable beachfront community on world-renowned Siesta Key. Completely rebuilt from the studs up in 2025, this beautifully transformed one-bedroom, one-bath, ground-floor residence combines contemporary coastal elegance, thoughtful design, and effortless island living with the added appeal of an established vacation rental history. Enter inside to discover a bright, inviting, open-concept interior showcasing a fresh coastal-inspired design and quality finishes throughout. Beautiful Cali longboard luxury vinyl plank flooring creates a seamless flow between living spaces, while the completely renovated kitchen features crisp white Shaker-style soft-close cabinetry, gleaming granite countertops, a ceramic tile backsplash, and new stainless-steel appliances. The beautifully remodeled bath is equally impressive, featuring a spacious walk-in shower with ceramic tile surround, a new white Shaker-style vanity, and updated fixtures. Additional enhancements include a hurricane-rated sliding glass door and front entry door, along with the everyday convenience of an interior laundry room equipped with a stacked washer and dryer. Extend your living space outdoors to the generously sized patio, an inviting setting for morning coffee, afternoon relaxation, or evening cocktails amid lush tropical surroundings. Overlooking one of the community's sparkling swimming pools just a short distance away, this outdoor retreat enhances the relaxed, resort-style atmosphere. Best of all, the Gulf's turquoise waters and Siesta Key's legendary powder-soft quartz sand are only a short stroll from your doorstep! Jamaica Royale is a beautifully maintained beachfront community offering approximately 300 feet of private deeded beach frontage and an impressive collection of resort-style amenities. Residents and guests enjoy three heated swimming pools, including a beachfront pool, lush tropical landscaping, shuffleboard courts, community grilling areas, and newly renovated beachside restrooms and changing facilities. One assigned parking space adds convenience, while nearby public tennis courts offer additional recreational opportunities. Pet owners will appreciate that pets are permitted for condominium owners, subject to community restrictions, while tenants are not permitted to have pets. Spend sun-filled days on the beach, enjoy spectacular Gulf sunsets, and embrace the laid-back elegance of Siesta Key living. Exploring the island is effortless, with a complimentary shuttle stop directly in front of the community providing convenient access to Siesta Key Village's acclaimed restaurants, charming boutiques, entertainment, and vibrant nightlife. Turnkey furnished and move-in or rental ready! This exceptional residence offers immediate enjoyment and attractive income potential, with an established rental history, existing future bookings, and participation in the TSA Prime rental program. Whether you're seeking a personal beachfront escape, a seasonal winter retreat, or an income-producing vacation rental, this extensively renovated condominium delivers an outstanding combination of location, lifestyle, and investment appeal. Experience the best of Siesta Key, where every day feels like a vacation!

5830 Midnight Pass Road Unit 38, 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
6287 Midnight Pass Road Unit 103, Sarasota
$619,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Priced to sell. Welcome to your sunny slice of paradise on Siesta Key. This bright and inviting south-facing condominium offers a great opportunity to enjoy island living just near the world-famous white quartz sand of Siesta Beach. This generously sized two-bedroom, two-bath residence has been well maintained by its original owner and occasionally occupied. The desirable southern exposure fills the condominium with natural light throughout the day, creating an open and welcoming atmosphere. The interior has been recently painted, giving the home a fresh, clean look, ready for your personal touches. The unit includes several updates, including a newer stack washer and dryer, newer air-conditioning system, plus energy-efficient LED lighting. The spacious layout provides comfortable living and dining areas along with a generously sized main bedroom en suite, making it ideal for year-round living, seasonal use or taking advantage of the Excelsior on-site rental program with a two-week rental minimum. Convenience is key with under-building assigned parking as well as a private storage closet for beach chairs, umbrellas and other beach essentials. This bay-to-beach complex offers an easy distance across the street to the powdery sand and turquoise Gulf waters of internationally recognized Siesta Key Beach. Residents and renters enjoy an impressive array of resort-style amenities. The property features tennis and pickleball courts, beautifully maintained grounds, bayside grilling areas, and bayside and Gulf-side swimming pools. Whether you prefer relaxing by the water, enjoying sunset walks along the beach or staying active with outdoor recreation, this community offers something for everyone. With its prime location, bright southern exposure and access to outstanding amenities, this Siesta Key condominium presents a wonderful opportunity to own a piece of Florida’s sought-after coastal lifestyle.

6287 Midnight Pass Road Unit 103, 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
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