Siesta Key Homes with Clubhouse Community Features

Siesta Key Homes with Clubhouse Community Features

Welcome to Siesta Key, Florida – a tropical paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant culture, and charming coastal lifestyle. With its powdery white sands and crystal-clear waters, Siesta Key is not just a destination; it’s a way of life. This idyllic barrier island offers residents and visitors alike an unparalleled blend of relaxation, recreation, and community spirit.

The homes in Siesta Key are as diverse as the residents who inhabit them. Among these properties, you'll find exquisite homes within clubhouse communities that cater to those seeking a resort-style living experience. These communities are designed to enhance your lifestyle with a variety of amenities that foster connection and leisure. Picture yourself unwinding by the sparkling pool, enjoying a game of tennis, or hosting gatherings in beautifully appointed clubhouses.

Living in a clubhouse community in Siesta Key means more than just a home; it’s about embracing a lifestyle filled with social opportunities and recreational activities. The sense of camaraderie among neighbors creates a warm and inviting atmosphere, perfect for making lasting memories with friends and family.

Beyond the amenities, Siesta Key boasts a rich tapestry of local attractions, from boutique shopping and gourmet dining to vibrant nightlife and cultural events. Whether you’re strolling along the beach at sunset or exploring the lush parks, life in Siesta Key is a delightful blend of relaxation and adventure. Discover your dream home in this captivating coastal community and experience the best that Florida living has to offer!

Newest Siesta Key Homes with Clubhouse Community Features

$719,000
2 Beds ⋅ 2 Baths ⋅ Casa Blanca Villas SubDv. ⋅ 34242 Zip Code
Welcome to Paradise, your own spot at SIESTA Key beach! Cozy and well-appointed for a long stay or a short time too. This villa has the LARGER square footage (1064 sq ft) in the Casa Blanca community. The property is part of the onsite rental program with some future bookings. Buyer has the option to continue or not. Boasting 2 large bedrooms and 2 full baths with the possibility to sleep 6, this is a family friendly place for beach trips. And this unit can hold the whole family nicely. Community heated pool is large, and lounge chairs are plentiful. Club house area is getting some updates and will be ready soon. Casa Blanca has an onsite manager; guests will have an easy time with keys and questions. Security cameras and a gate at the exit, plus a security guard can be there at peak times Renovated from top to bottom and completed in Feb of 2026, including new storm/hurricane windows and doors, the unit is sold turnkey, ready for rental income or immediate use. Furnished with neutral colors, it gives the beachy vibe, essential for relaxed stays. Kitchen is filled with all the necessary equipment to prep meals and snacks. Full size fridge and stove and a handy dishwasher, bring all your favorite groceries and eat in. The cabinets hold all you will need. Splashing in the Gulf or building a sandcastle it's easy to see why Siesta Beach is highly rated, LOCATION IS TRULY AMAZING, close to the charming village area with shops and dining choices or take the trolley for a free ride to other beach spots! The choices off the key are also quite vast. Florida studio Theater is in nearby downtown Sarasota, also the Opera house, Movie theaters, and the Ringling museum is fascinating for a day of exploration of the area's circus history. Mote Sea Aquarium is near and a must do for visitors. UTC, a modern mall, that has a superior collection of shopping, food and fun things to do. Stroll along the large lake at Benderson Park. Play golf at any of the highly rated courses. Fishing and boating options are available, choose a paddle tour, check out Myakka State Park, or the trail at Rothenbach Park for a day in nature. Bird watching is Audubon worthy at the Celery Fields. This barely scratches the surface of our Florida lifestyle, come and see Casa Blanca and you will want to STAY!

6154 Midnight Pass Road Unit 6-C, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Virtually Staged. Rarely available 5th-floor residence in Siesta Gulf View’s coveted 08 stack. This exceptional beach retreat showcases an extended wrap balcony with unobstructed west and south panoramic views of Siesta Key’s white-sand beaches and glowing Gulf sunsets. Bathed in natural light, the spacious split-bedroom layout offers walk-in closets in both bedrooms, motorized storm shutters, an interior laundry room, and abundant flexibility to create a tailored coastal home—reimagine the breakfast nook as a den or keep the expansive office area. Offered for the first time in nearly 30 years, this is a rare opportunity to personalize a premier view property. Enjoy deeded beach access via the private community boardwalk, along with a pool, tennis, pickleball, fitness room, clubhouse with meeting room and kitchen, and beachside grilling and seating area—all within Siesta Gulf View’s intimate 59-residence setting, just two blocks to famous Siesta Key Village.

420 Beach Road Unit 508, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Experience the best of Siesta Key living in this beautifully renovated first-floor condominium at Beach Way. Located directly across from the world-famous Siesta Key Beach and just a short stroll to Siesta Key Village, this 2-bedroom, 2-bath residence offers the perfect combination of luxury, convenience, and investment potential. Inside, you'll find a thoughtfully updated interior featuring elegant quartz countertops, brand-new stainless steel appliances, durable Cali luxury vinyl plank flooring throughout, and a bright, open floor plan that flows seamlessly into the enclosed lanai. The lanai overlooks the tropical landscaping with a partial view of the community pool, creating the perfect place to relax after a day at the beach. Built for peace of mind, the unit features PGT WinGuard impact-resistant windows (Series 710) and PGT 700 Series impact-resistant sliding glass doors. Convenience continues outside with assigned covered parking located directly in front of the unit, along with ample guest parking for family and friends. Beach Way's desirable monthly rental policy makes this property an excellent option for a primary residence, vacation home, seasonal retreat, or income-producing investment. Enjoy resort-style coastal living just steps from the white quartz sand of world-famous Siesta Key Beach, with the Siesta Key Trolley stop conveniently located right in front of the community for effortless access to Siesta Key Village, shopping, dining, entertainment, and everything the island has to offer.

5600 Beach Way Drive Unit 109, Sarasota
$544,900
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Welcome to your own slice of paradise at Jamaica Royale on world-famous Siesta Key. This beautifully updated, turnkey one-bedroom, one-bath villa offers the convenience of ground-floor living in an all-ground-level association, meaning no stairs and no milestone inspections required. Renovated in 2025, this villa is move-in ready and ideally positioned with relaxing views. Jamaica Royale is a sought-after beachfront community featuring three swimming pools, private beach access with lounge chairs, grilling areas, shuffleboard, and a variety of recreational amenities, creating the perfect setting for both relaxation and fun. Whether you're searching for a personal beach retreat or a proven investment property, this villa delivers. With a strong rental history and existing bookings, it offers immediate income potential while giving you the opportunity to enjoy the sugar-white sands and turquoise waters of Siesta Key whenever you choose. As the best-priced turnkey one-bedroom villa currently available in Jamaica Royale, this is an exceptional opportunity to own a beachfront getaway at an outstanding value. Schedule your private showing today!

5830 Midnight Pass Road Unit 43, Sarasota
$509,000
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
$649,900
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Ready to Enjoy the Great Life? Welcome to your own piece of paradise at Island Reef, one of Siesta Key's most sought-after Gulf-to-Bay Communities. Perfectly positioned in the desirable "A" Building, this beautifully maintained and furnished second-floor end unit offers breathtaking panoramic views of the Gulf of Mexico from the moment you walk through the door. Natural light pours into the residence, while expansive water views create a peaceful backdrop that defines true coastal living. Offering over 1,200 square feet, this two-bedroom, two-bath residence features a desirable split-bedroom floor plan that provides comfort and privacy for both owners and guests. Thoughtfully updated over the years and offered turnkey furnished, the condo is ready to enjoy immediately while still providing the opportunity to personalize over time. Whether you're preparing dinner with the Gulf as your backdrop, enjoying your morning coffee on the lanai, or ending the day with one of Siesta Key's unforgettable sunsets, every space is designed to embrace the waterfront lifestyle. Life at Island Reef extends well beyond your front door. Begin your mornings with a walk along the private beach at Turtle Beach, spend afternoons kayaking or paddleboarding through Little Sarasota Bay, or watch dolphins play in the Gulf from the community's beachfront pool. Boating enthusiasts will appreciate the community's bayside docks with lift capability and direct access to Sarasota Bay and the Intracoastal Waterway. Residents enjoy an impressive collection of resort-style amenities, including two heated pools, private beach access, tennis and pickleball courts, shuffleboard, a fitness center, clubhouse, library, fishing pier, kayak and bike storage, beautifully landscaped walking paths, on-site management, and covered parking. Ideally located on the quieter southern end of Siesta Key, Island Reef offers a relaxed coastal atmosphere while remaining just minutes from Siesta Key Village's dining, shopping, and entertainment. Don't forget to check out the complimentary trolley that goes directly to the village!! Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this is a Rare Opportunity to own a beautifully furnished & spacious Gulf-front Condominium in Island Reef one of Siesta Key's premier Gulf-to-Bay communities, where lush tropical landscaping, resort-style amenities, private beach access and unmatched Coastal lifestyle come together harmoniously to create the perfect place to feel at Home. Call today to Book a Private Showing - these opportunities don't last long!

8764 Midnight Pass Road Unit A201, Sarasota
$1,589,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Welcome to Dolphin Bay, one of Siesta Key's premier waterfront communities, where luxury coastal living meets breathtaking scenery. This beautifully maintained 2-bedroom, 2-bath residence offers 2,217 square feet of thoughtfully designed living space with panoramic views of the Intracoastal Waterway, downtown Sarasota, and beyond. Filled with natural light, the open-concept floor plan was designed to maximize the spectacular waterfront views. Floor-to-ceiling windows create an inviting atmosphere where you can relax, entertain, and watch boats glide by as the Sarasota skyline transforms from sunrise to sunset. The spacious kitchen offers abundant cabinetry, generous counter space, Thermador appliances, and a breakfast area that opens seamlessly to the main living spaces, making everyday living and entertaining effortless. Wake up each morning to stunning water views from the luxurious primary suite, complete with a spacious walk-in closet and a spa-inspired en-suite bath featuring a large walk-in shower. The generously sized guest suite also features a large walk-in closet and is conveniently located adjacent to a full bath, providing exceptional comfort and privacy for family and guests. Life at Dolphin Bay extends far beyond your residence. Enjoy resort-style amenities including a pool and spa, Har-Tru tennis courts, fitness center, elegant clubhouse, kayak launch, fishing pier, and day dock with direct access to Sarasota Bay and the Gulf. Perfectly positioned just minutes from the award-winning white quartz sands of Siesta Key Beach, this exceptional residence also places you close to the restaurants, boutiques, and vibrant atmosphere of Siesta Key Village. A short drive brings you to downtown Sarasota, home to the Van Wezel Performing Arts Hall, Sarasota Opera House, The John and Mable Ringling Museum of Art, waterfront parks, fine dining, galleries, shopping, and year-round cultural events. Whether you're searching for a full-time waterfront residence, a seasonal retreat, or the ultimate Florida lifestyle, this exceptional Dolphin Bay residence offers the rare opportunity to enjoy luxury, boating, world-class beaches, and breathtaking waterfront views—all in one of Siesta Key's most desirable communities.

1280 Dolphin Bay Way Unit 402, Sarasota
$399,000
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
$480,000
3 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
This rare, freestanding 3-bedroom, 2-bath villa presents an exceptional opportunity to create the coastal home you've always envisioned in the premier Gulf front community of Whispering Sands. With its highly desirable floor plan, attached 2-car garage, and private fenced patio, this residence offers the perfect foundation for a truly personalized retreat. Professionally remediated following Hurricane Helene, this villa is being offered in its current condition. Featuring concrete floors, partial drywall, and no kitchen or bathroom fixtures, this residence offers a true blank canvas – inviting you to select every finish, fixture, and detail to create a home that reflects your own style and vision. Washer and dryer hookup is located in the garage. Important exterior improvements have already been completed, including NEW 2025 villa and garage roofs and fresh exterior paint, while a comprehensive two-year community landscaping enhancement plan is in the planning stages. Life at Whispering Sands is about far more than just your residence. Enjoy 800 feet of PRIVATE quartz sand beach, two heated pools, clubhouse (currently undergoing complete remodeling that will also include a catering kitchen and fitness rooms), beachside Tiki Hut, shuffleboard courts, canoe/kayak storage, and professionally maintained grounds, all just a short stroll from the shops, restaurants, and vibrant charm of Siesta Key Village. The comprehensive HOA fee includes cable, high speed internet, recreational amenities, landscaping, reserves escrow, HOA insurance, on-site management & maintenance team, security, water and sewer – allowing you to spend more time enjoying the island lifestyle. Freestanding villas in Whispering Sands are exceptionally rare. This is a unique opportunity to create a home that reflects your personal taste while enjoying maintenance-free living in one of Siesta Key's most desirable 55+ Gulf front communities.

208 Hourglass Way Unit V11, Sarasota
$1,559,000
2 Beds ⋅ 2 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and durability. Situated directly on Siesta Key Beach, and built with walls of sliding glass doors in every room to take advantage of the diverse, magnificent views in all directions. This is the penthouse being offered turnkey furnished. Fantastic views in all directions. It's perfect location on the island within walking distance to Siesta Key Village, and all its offerings. The rooftop saltwater pool is a beautiful addition that provides privacy and lovely beach views. Take a cocktail out to watch the sunset over the water! The building itself has undergone significant upgrades, making it a prestigious address on Siesta Key. Complete replacement of cast-iron pipes, geothermal well driven HVAC system keeps cost low, new generator for entire building, monitored water sensors in all units, installation of new gates at the front entrance. The elevators have been replaced, the lobby has been redone, and is a waterfront masterpiece. Only the 4 penthouse units have use of the rooftop with decks. Come see for yourself why this stunning property is so very special.

5400 Ocean Boulevard Unit 17-04, Sarasota
$499,000
2 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
New Listing Photos now attached! Weekly rentals, prime Siesta Key location, and immediate income potential—this is the beach investment opportunity buyers wait for. Welcome to Bay Oaks, where island living meets exceptional rental flexibility in one of the most desirable communities on Siesta Key. This beautifully updated 2-bedroom, 2-bath condo is being offered fully turn-key furnished, making ownership effortless from day one. Even better, future rental bookings are already in place, allowing you to start generating income immediately—no waiting, no setup, no downtime. Just close and collect. Since its last listing, the home has been enhanced with a newly renovated kitchen, featuring stylish modern finishes that elevate both form and function. The bright, open-concept layout creates an inviting coastal feel, with seamless flow between the kitchen, dining, and living spaces—perfect for relaxing after a day at the beach or entertaining guests. Enjoy peaceful mornings on your private balcony surrounded by lush tropical landscaping, while both spacious bedrooms provide comfortable retreats filled with natural light. Bay Oaks is beloved for its unbeatable location and resort-style amenities. Situated on the bayside of Siesta Key and just moments from the powdery sands of world-famous Siesta Key Beach, residents and guests enjoy access to a sparkling pool, private fishing pier, tennis courts, shuffleboard, and beautifully maintained grounds. Hop on the free trolley for quick access to the restaurants, boutiques, and nightlife of Siesta Key Village. For investors, the biggest advantage is Bay Oaks’ highly desirable weekly rental policy—a rare and valuable feature on Siesta Key that opens the door to strong vacation rental demand and attractive income potential. Whether you're searching for a personal beach getaway, a savvy investment property, or the perfect combination of both, this Bay Oaks condo delivers. Flip-flops encouraged. **Updated Listing Photos Now Attached!**

6157 Midnight Pass Road Unit E12, Sarasota
$569,000
2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code
A Wonderful, Beachside Opportunity Awaits in Vista Hermosa! Discover the ultimate turnkey coastal lifestyle with this newly renovated, beautifully furnished 2-bedroom, 2-bathroom villa condominium (furnishings included). Step inside to find stunning beach-oriented finishes, brand-new ceramic plank flooring, new appliances, and modern cabinets and countertops. Perfectly positioned within easy walking distance of both Crescent Beach and the world-famous Siesta Key Beach, this home lets you spend your days playing in the sand and surf and your evenings soaking in dramatic, world-class sunsets. After a long day in the sun, relax in the sparkling Vista Hermosa community pool. This villa offers premium convenience with an attached carport and a well-sized private laundry room that doubles as excellent storage for your beach chairs, toys, and fishing gear. Step outside for a brief walk to shopping and popular beach-themed restaurants, including the Daiquiri Deck and Captain Curt's. Want to explore further? Hop on the free Siesta Islander trolley for an easy ride up to Siesta Village to enjoy its endless souvenir shops and diverse breakfast, lunch, and dinner dining options. Whether you are seeking a permanent tropical retreat or a lucrative island getaway, this gorgeous villa offers the absolute best of Siesta Key living!

161 Vista Hermosa Circle Unit 26A, Sarasota
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