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 Siesta Key, nestled in Sarasota County, Florida. Known for its stunning white sandy beaches and vibrant coastal atmosphere, Siesta Key is more than just a vacation destination—it's a lifestyle. With its laid-back vibe and breathtaking sunsets, this charming island community offers an idyllic setting for those seeking both relaxation and adventure.

Crescent Beach, one of Siesta Key's crown jewels, boasts crystal-clear waters and is perfect for sunbathing, swimming, and beachcombing. This serene stretch of shoreline is ideal for families and beach lovers alike, providing a tranquil escape from the daily grind. The nearby Siesta Key Village offers a delightful array of shops, restaurants, and entertainment options, ensuring that residents and visitors can enjoy a lively social scene while savoring the local flavors.

For those considering a home in this coastal haven, you’ll find an array of properties featuring inviting pools that enhance the outdoor living experience. Imagine soaking up the Florida sun by your private pool, hosting gatherings with friends and family, or simply unwinding after a day at the beach. Many homes in this community are designed to blend seamlessly with the natural beauty of the surroundings, offering spacious layouts, modern amenities, and easy access to the beach.

Living in Siesta Key means embracing a vibrant lifestyle filled with outdoor activities, cultural experiences, and a strong sense of community. Whether you’re drawn to the allure of Crescent Beach or the charm of local shops and eateries, this coastal paradise is waiting to welcome you home. Discover your dream home in Siesta Key today, where every day feels like a vacation!

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

1229 Moonmist Circle Unit P6, Siesta Key
$625,000
2 Beds ⋅ 2 Baths ⋅ G5118459 MLS ⋅ N/A BLDG.
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, Siesta Key
1250 N Portofino Drive Unit 304, Siesta Key
$394,000
1 Beds ⋅ 2 Baths ⋅ A4708535 MLS ⋅ Marlin House BLDG.
Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite counters, glass backsplash, peninsula seating, and stainless appliances. Bathrooms feature quartz vanities and tiled showers; guest bath includes a soaking tub. Impact windows, same-floor laundry, and private storage add convenience. Siesta Harbor, a 55+ community, offers private beach access, heated pool/spa, lush landscaping, fishing pier, and a full calendar of social activities. Dock leases may be available for boats up to 30’. Additional amenities include covered parking, on-site manager, and a new roof (2025). Ideally located off the South Bridge near dining, shops, and the free Siesta Key trolley, this turnkey condo is perfect as a vacation retreat, full-time residence, or investment.

1250 N Portofino Drive Unit 304, Siesta Key
6006 Midnight Pass Road Unit 11, Siesta Key
$449,000
1 Beds ⋅ 1 Baths ⋅ A4708157 MLS ⋅ B BLDG.
Your opportunity to own on Siesta Key at an exceptional value with nearly 200 feet of deeded beach frontage! The lowest-priced condo on Siesta Key, this TURN KEY, charming 1-bedroom, 1-bath plus two additional sleeper sofas at Casa Mar offers an incredible opportunity for an island retreat, seasonal escape or income-producing vacation rental. Possibilities are endless! Just steps away from Siesta Key’s world-famous white quartz sand beaches and the turquoise waters of the Gulf of Mexico, this beachside condo offers 600 sq. ft condo of interior living, 108 sq. ft. of screened-in lanai, AND a brand new outdoor paver patio that is being completed as we speak which will be so cute set up as an outdoor seating area! Inside, vintage island character meets relaxed coastal living with freshly painted vaulted wood-beamed ceilings, timeless terrazzo flooring, abundant natural light, and an open living area flowing seamlessly to the screened lanai, an ideal spot for morning coffee or unwinding after a day at the beach. The kitchen features solid-surface countertops, eat-in dining area and opens to the main living space, while the spacious bedroom offers ample storage including built-in closet cabinetry. The bathroom includes a walk-in shower. Recent improvements include a new A/C in 2025, new building roof in 2024, water heater in 2021, and partial impact windows. An assigned covered carport is located directly outside your ground floor private entrance, making everyday access effortless with no stairs to navigate. Casa Mar delivers the Siesta Key lifestyle buyers dream of with private deeded beach frontage, two covered beach pavilions, two community pools, tennis and pickleball, basketball, clubhouse, four BBQ grilling areas with picnic tables, and community laundry facilities. The condo fee includes cable TV, internet, water/sewer, building insurance, and grounds maintenance. Even better, the Siesta Key Breeze Trolley stops right at the Casa Mar entrance on Midnight Pass Rd, offering convenient transportation around the island whether you’re enjoying a night on the town in the village or Turtle Beach on the south end. Whether looking for an affordable slice of Siesta Key to call your own, a lock-and-leave beach getaway that can also serve as both a vacation home and an income generating vacation rental, this is one you won't want to miss. Siesta Key Beach! Exceptional amenities! Weekly rentals! AND the lowest-priced condo on Siesta Key, this is your chance to own your piece of the island!

6006 Midnight Pass Road Unit 11, Siesta Key
5600 Beach Way Drive Unit 207, Siesta Key
$739,000
2 Beds ⋅ 2 Baths ⋅ A4708437 MLS ⋅ 5600 BLDG.
LOCATION, LOCATION, LOCATION! This beautifully updated 2 bed, 2 bath home, ideally located directly across from world-famous Siesta Key Beach. Offering views of the pool, lush landscaping, and a partial ocean view, this gorgeous turnkey furnished residence combines a relaxed coastal setting with an exceptional location. The thoughtfully updated interior features luxury vinyl plank flooring throughout and a stunning kitchen with custom cabinetry, quartz countertops, a subway and mosaic-style backsplash, and a center island with convenient breakfast seating. The defined dining and living areas provide a comfortable space for both everyday living and entertaining, with sliding glass doors extending the living space onto the balcony and bringing the outdoors in. The primary suite offers an ensuite bath, walk-in closet, and its own sliders leading to the balcony. The spacious guest bedroom includes a Murphy bed cabinet, providing flexibility for guests when needed, along with a second full bath. Benefiting from hurricane impact windows for peace of mind this tastefully decorated home is ready to enjoy from day one! Step outside and enjoy the peaceful surroundings from the private balcony or take advantage of the unbeatable location just across from Siesta Key Beach. Stroll to the Village for its lively music, dining, and shopping, or hop aboard the free beach trolley for an easy way to explore the island. With Sarasota's downtown arts, culture, dining, and entertainment just a short drive away, along with the boutiques, restaurants, and waterfront atmosphere of St. Armands Circle, this property offers the perfect balance of beach living and convenience. Whether you're looking for a vacation home, a place to escape and enjoy the Florida lifestyle, or an investment opportunity, this inviting Siesta Key residence offers a wonderful combination of location, updates, and relaxed coastal living.

5600 Beach Way Drive Unit 207, Siesta Key
6300 Midnight Pass Road Unit 1005, Siesta Key
$1,275,000
2 Beds ⋅ 2 Baths ⋅ A4706234 MLS ⋅ N/A BLDG.
Full gulf views and right on the beach! Experience breathtaking coastal living from this spectacular 10th-floor condominium at Crystal Sands on Siesta Key being offered turnkey furnished. Enjoy panoramic beach and gulf views from the living areas and both bedrooms, creating an incredible backdrop for morning coffee, relaxing afternoons, and unforgettable sunsets. From this elevated vantage point, you'll also enjoy beautiful views of downtown Sarasota. Located directly on Siesta Key's desirable Crescent Beach, this residence offers the quintessential Florida beach lifestyle. The comfortable floor plan features spacious living areas, luxury vinyl plank flooring, newer appliances and a 30-foot lanai accessible from the living room and both bedrooms. Excellent rental income opportunity with 2-week rentals permitted and an onsite rental management staff to handle every detail. Enjoy the flexibility of using the condominium as your own private beach retreat while generating rental income when you're away. Whether you're looking for a vacation home, investment property, or the perfect combination of both, this is a rare opportunity to own a gulf-view residence in one of Sarasota's most desirable locations. Pet friendly.

6300 Midnight Pass Road Unit 1005, Siesta Key
4822 Ocean Boulevard Unit 8B, Siesta Key
$649,000
2 Beds ⋅ 2 Baths ⋅ A4708261 MLS ⋅ Siesta Towers BLDG.
Sweeping water views across Big Pass to the Gulf of Mexico and year-round sunsets set the stage for this oversized 2-bedroom, 2-bath residence in Siesta Towers on Siesta Key. A rare 40+ foot-long balcony stretches across the residence, while inside, 1,435 square feet, generously sized rooms and a flexible floor plan offer endless possibilities to create your own coastal retreat. Similar floor plans have been reimagined to include a den or flex space, and an in-unit washer and dryer may be added. Hurricane-impact sliders and windows frame the views and fill the residence with natural light. Siesta Towers has undergone extensive improvements, including a new seawall, renovated exterior, new landscaping, rebuilt fishing and social piers, renovated pool and fencing, Garrison flood-control system, replaced electrical system and key-fob/app-controlled access. Residents also enjoy a fitness center, social room, outdoor grills, bike room and private storage.

4822 Ocean Boulevard Unit 8B, Siesta Key
5830 Midnight Pass Road Unit 18, Siesta Key
$549,000
1 Beds ⋅ 1 Baths ⋅ A4706335 MLS ⋅ Jamaica Royale Unit One BLDG.
The nicest 1-BR villa at the beautiful Jamaica Royale on Siesta Key -and- SELLER FINANCING AVAILABLE -- at the #1 Beach in America! This beautifully renovated ground floor 1-bedroom villa is offered completely turnkey furnished and has been used exclusively by the owner and maintained as a personal beach retreat. / The renovation features an impressive collection of upgrades and high-end finishes, including Crema Marfil chiseled-edge marble floors, blue quartz kitchen countertops, a striking mother-of-pearl kitchen backsplash, beautiful white shaker kitchen cabinets, and recessed lighting. The bathroom is beautifully finished in natural travertine stone with frameless glass shower doors and a hydro-flush toilet. The kitchen is equipped with brand new stainless-steel appliances, including an LG counter-depth refrigerator. Also featured are impact windows and doors, a brand-new A/C system, new Rheem 50-gallon water heater, and new Whirlpool stackable washer/dryer. The villa is furnished with brand-new furniture, including two queen beds and a 75-inch flat-screen TV. Everything is in place for your immediate personal enjoyment or rental use. / With strong demand for vacation rentals on Siesta Key, this property offers estimated rental income of $50,000–$60,000 annually, while still providing the opportunity to enjoy it personally as desired. An onsite professional rental office provides convenient year-round rental management, or owners may choose to self-manage their rentals. / Jamaica Royale is a direct oceanfront gated community, and offers an exceptional beachfront lifestyle with its private beach and powder-soft white quartz sand, direct frontage to the Gulf of Mexico's crystal-clear waters, three heated swimming pools, resort-style amenities, community gas-grills, recreational facilities, and stunning Gulf sunsets. New carports are currently anticipated for 2027. No milestone inspections. The very desirable Building 1-22 villa row offers exceptionally close and convenient beach access -and- south facing patio sunshine. / Whether you are looking for a turnkey Siesta Key beach retreat or an income-producing vacation rental, this exceptionally well-appointed completely-renovated villa combines a premier beach location, brand-new furnishings, and the flexibility to enjoy the property yourself and/or generate rental income. / This is a fantastic opportunity to own quality beachfront real estate at the #1 Beach in America. With SELLER FINANCING AVAILABLE, don’t miss this one!

5830 Midnight Pass Road Unit 18, Siesta Key
1350 Siesta Bayside Drive Unit 1350B, Siesta Key
$899,000
3 Beds ⋅ 2 Baths ⋅ A4708214 MLS ⋅ 1350 BLDG.
Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in nearby Building 1328 on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multigenerational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddleboarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.

1350 Siesta Bayside Drive Unit 1350B, Siesta Key
1328 Siesta Bayside Drive Unit 1328C, Siesta Key
$699,000
2 Beds ⋅ 2 Baths ⋅ A4708199 MLS ⋅ Gulf & Bay Club Bayside BLDG.
Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the second floor, a townhome layout. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.

1328 Siesta Bayside Drive Unit 1328C, Siesta Key
9397 Midnight Pass Road Unit 506, Siesta Key
$665,000
2 Beds ⋅ 2 Baths ⋅ A4707551 MLS ⋅ South BLDG.
LIVE WHERE THE GULF MEETS THE BAY. Discover an extraordinary island lifestyle at The Pointe on Midnight Pass, a private, gated, waterfront community at the southernmost tip of Siesta Key, uniquely positioned at the convergence of The Gulf of America, Little Sarasota Bay, and Blind Pass Lagoon. This beautifully renovated 2-bedroom, 2-bath residence captures the rare magic of both sides of the island—wake to spectacular sunrises over Little Sarasota Bay and the Jim Neville Nature Preserve, then watch the sky transform at sunset over The Gulf. Thoughtfully updated, the residence features elegant tray ceilings and recessed lighting, solid-wood cabinetry, granite countertops, stainless-steel appliances, breakfast bar and pantry, contemporary baths with floor-to-ceiling tile, ceramic tile flooring throughout, sleek white interior doors, and sun-control shades on the lanai. A spacious lanai extends the living space outdoors, creating the perfect setting for morning coffee, sunset cocktails, or watching dolphins, manatees, seabirds and boats move through the surrounding waters. A private utility room houses the washer and dryer, while ground-level storage provides coveted space for beach, boating and golf gear. And then there is The Pointe—more than five acres of waterfront living, surrounded by water on three sides and embraced by an extensive seawall, with pathways winding throughout lush, mature tropical vegetation. Enjoy a heated pool and spa, lighted tennis and pickleball courts, fitness center, sauna, clubhouse, private island pavilion with grills, kayak and canoe storage and launches, fishing areas, boat docks, and on-site management—with a vibrant social calendar during season that brings neighbors together and makes it easy to connect, participate, or simply enjoy the island lifestyle at your own pace. The newly reopened Midnight Pass adds another extraordinary dimension, reconnecting the Gulf and Intracoastal waters and enhancing the boating, fishing and wildlife experience right outside your door. Walk or bike to Turtle Beach, enjoy nearby restaurants, or take the trolley to explore more of Siesta Key. This is not simply a condominium—it is the rare opportunity to own a front-row seat to the natural beauty, wildlife and ever-changing waters of southern Siesta Key.

9397 Midnight Pass Road Unit 506, Siesta Key
5855 Midnight Pass Road Unit 221, Siesta Key
$634,900
2 Beds ⋅ 2 Baths ⋅ A4707649 MLS ⋅ Harbor Towers BLDG.
Beautiful turnkey 2-bedroom 2 bath condo in Harbor Towers! All new hurricane windows, window shades, new plumbing for entire home and hot water heater 2025. Master bedroom has walk in closet, renovated bath with floating vanity and tub/ shower combo. Second bedroom is large with lots of windows and connected bath with tub / shower and floating vanity. Dining room and Living room combo with open floor plan. Hurricane windows across the entire front of condo give lots of sun and nice view of the lake. This unit includes a covered parking spot ($15.000 value). Rental income is very strong with on-site management. Unit currently rented Feb 13, 2027- March 20th, 2027. Great rental Income! This property features many amenities, including, heated pool with kiddie pool, 2 BBQ areas, social room with renovated kitchen, Har-Tru tennis courts, fitness room, kayak storage, harbor with boat slip rental. Close proximity to Siesta Key beach. Harbor Towers also offers one of the lower HOA fees on the key for all that is included.

5855 Midnight Pass Road Unit 221, Siesta Key
4708 Ocean Boulevard Unit E4, Siesta Key
$2,199,000
3 Beds ⋅ 3 Baths ⋅ A4707998 MLS ⋅ Windward Passage BLDG.
Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.

4708 Ocean Boulevard Unit E4, Siesta Key
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