Siesta Key Homes with Tennis Court(s) Amenities

Siesta Key Homes with Tennis Court(s) Amenities

Welcome to Siesta Key, a stunning barrier island located in the state of Florida. Known for its pristine white sandy beaches and vibrant community, Siesta Key offers a unique blend of natural beauty and modern amenities.

For those who enjoy an active lifestyle, homes with tennis court amenities are a popular choice in Siesta Key. Imagine starting your day with a friendly match on your private court, surrounded by lush tropical landscaping and warm sunshine. Whether you are a seasoned player or just looking to have fun, having a tennis court at your disposal adds an extra touch of luxury to your everyday life.

Siesta Key is not only a paradise for tennis enthusiasts but also a haven for beach lovers, foodies, and nature enthusiasts. Explore the eclectic mix of shops and restaurants in Siesta Village, take a leisurely stroll along the award-winning Siesta Beach, or embark on a kayaking adventure in the tranquil waters of the Gulf of Mexico.

With its laid-back atmosphere and endless recreational opportunities, Siesta Key offers the perfect blend of relaxation and excitement. Whether you are looking for a permanent residence or a vacation home, Siesta Key has something for everyone. Come and experience the magic of Siesta Key – where everyday life feels like a holiday.

Newest Siesta Key Homes with Tennis Court(s) Amenities

1350 Siesta Bayside Drive Unit 1350B, Sarasota
$899,000
3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
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, Sarasota

1328 Siesta Bayside Drive Unit 1328C, Sarasota
$699,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
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, Sarasota

9397 Midnight Pass Road Unit 506, Sarasota
$665,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
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, Sarasota

8750 Midnight Pass Road Unit 501C, Sarasota
$699,900
2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
WELCOME TO TORTUGA ON SIESTA KEY, A TRUE TROPICAL COASTAL PARADISE! THIS 5TH-FLOOR 2-BEDROOM, 2-BATHROOM RESIDENCE SHOWCASES A SPRAWLING OPEN-CONCEPT LAYOUT WITH 1,232 SQUARE FEET OF LIVING SPACE, SWEEPING BEACH VIEWS, AND AN OVERSIZED 34-FOOT COMBINED LIVING AND FAMILY ROOM FILLED WITH NATURAL LIGHT. SITUATED ON OVER 3 ACRES OF DIRECT GULF-FRONT GROUNDS, THIS PROPERTY PRESENTS THE ULTIMATE BLEND OF ISLAND LUXURY AND RELAXATION. FRESHLY UPDATED WITH A MODERN COASTAL PALETTE, THE INTERIOR HIGHLIGHTS WOOD-LOOK LAMINATE FLOORS, CROWN MOLDING, NEUTRAL GREY ACCENTS, AND SLEEK CEILING FANS THROUGHOUT. THE PRIMARY SUITE SERVES AS A PRIVATE RETREAT FEATURING AN EXPANSIVE CLOSET WITH CUSTOM ORGANIZERS AND AN EN-SUITE BATHROOM WITH A GLASS-ENCLOSED WALK-IN SHOWER AND PEBBLE TILE FOOTING. THE SECOND BEDROOM AND FULL BATHROOM SHOWCASE PREMIUM FINISHES PERFECT FOR FAMILY OR GUESTS. INCLUDES A DEDICATED IN-UNIT LAUNDRY ROOM PLUS HURRICANE SHUTTERS FOR TOTAL PEACE OF MIND. THE TORTUGA COMMUNITY SHOWCASES RESORT-STYLE AMENITIES: DEEDED BEACH ACCESS DIRECTLY ONTO SIESTA KEY, AN INDOOR/OUTDOOR HEATED POOL, TENNIS COURTS, A CLUBHOUSE, AN ASSIGNED COVERED GARAGE SPACE, ELEVATOR ACCESS, AND A PRIVATE ENTRANCE. THE HOA FEE COVERS CABLE TV, INTERNET, WATER, SEWER, TRASH, PEST CONTROL, BUILDING MAINTENANCE, AND STRUCTURAL INSURANCE. CURRENT THREE DOCKS AVAILABLE FOR RENT FOR $300 PER YEAR UP TO 24 FT BOAT. EMBRACE THE ULTIMATE SIESTA KEY LIFESTYLE: WALK STRAIGHT ONTO THE SAND, ENJOY WATER ACTIVITIES, OR TAKE A SHORT DRIVE OVER STICKNEY POINT BRIDGE TO DOWNTOWN SARASOTA DINING, SHOPPING, AND ENTERTAINMENT. RENTAL-FRIENDLY (1-MONTH MINIMUM LEASE).CLOSE TO OPHELIAS WATERFRONT RESTAURANT AND TURTLE BEACH BOAT RAMP. COME EXPERIENCE COASTAL LIVING AT ITS FINEST!

8750 Midnight Pass Road Unit 501C, Sarasota

625 Beach Road Unit 301, Sarasota
$865,000
2 Beds ⋅ 2 Baths ⋅ Timber Land Ranchettes SubDv. ⋅ 34242 Zip Code
This beautifully furnished turnkey, two-bedroom, two-bath condominium, will charm you with the luxury of direct access to world renown ‘’Siesta Key Beach. Embrace a rare opportunity to own at ‘Tivoli By The Sea’, the perfect combination of a desirable island location with resort-style amenities. You’ll savor vivid sunsets and panoramic views of the Gulf’s turquoise waters, all from your 26-by-6-foot private balcony. This condo is in immaculate condition, and perfect for year-round living, seasonally, or as an investment property. The modern open floor plan creates a seamless indoor-outdoor flow throughout the home. Sliders from the spacious Dining Room/Living Room area offers plenty of space for entertaining. The Primary Bedroom suite, which features a king-size bed, a vanity area and walk-in closet, also has its own set of sliders to the oversized balcony. The contemporary eat-in kitchen is bright and pristine, with thoughtful updates. The large Guest Bedroom, and nearby full Guest Bath, provides family and guests with their own quiet respite. There’s also a top-floor one bedroom Guest suite, available to owners at affordable weekly reservations for their visiting guests (see the photos). ‘Tivoli By The Sea’ offers an impressive collection of amenities including: a heated swimming pool, fitness center, recreation room, tennis/pickleball court, basketball court, putting green, and ping-pong table. You’ll be a short stroll to the sugary sands of Siesta Key Beach from your private gate. The rooftop Club Room features stunning 270-degree gulf views, and can be reserved for private parties. Each condo includes a storage unit, a covered parking space, and hurricane shutter protection. The building has benefited from numerous updates in recent years. Plumbing updates in 2014, electrical updates in 2017, replacement of catwalk railings in 2019, resurfacing of the tennis and pickleball courts in 2020, and a new roof in 2023. 'Tivoli By The Sea' boasts a strong track record for weekly & monthly rentals, all handled by the on-site company, 'Beachside Management'. Less than five minutes from Siesta Key Village, the home affords convenient access to an array of restaurants, shops and nightlife. Parasailing, paddle boarding, kayaking, boating rentals, and fishing, all provide endless opportunities to enjoy the surrounding waters. Downtown Sarasota is a simple drive with its vibrant arts and entertainment scene. Your social calendar will be filled with tons of culture to enjoy with the ‘Van Wezel Performing Arts Hall’, ‘Sarasota Opera House’, ‘Asolo Repertory Theatre’, ‘Florida Studio Theatre’ and the ‘Marie Selby Botanical Gardens’. Sarasota-Bradenton International Airport is a short drive away. This wonderful condo is vacant and easy to show!

625 Beach Road Unit 301, Sarasota

5855 Midnight Pass Road Unit 605, Sarasota
$719,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Harbor Towers 605 represents a unique opportunity to live on a high floor in the building with the coveted south-facing views looking over the pool. Welcome to Harbor Towers, your home at the beach- this perennial favorite building is now better than ever after undergoing massive exterior renovations which include strengthening and impact glass windows and sliding doors for all units! The unique and large grounds of Harbor Towers provide a spectacular setting with lots of space to enjoy the coastal lifestyle. You are not just buying a home, you're buying into a Yacht and Tennis Club, with har-tru tennis courts, a recently revamped marina with inexpensive boat mooring prices, a heated community pool, fitness center, meeting area, community kayak area and much much more. This unit has been renovated and lovingly cared for over the years. Besides the impeccable view down the Intracoastal Waterway, this unit offers well maintained luxury featuring tile floors throughout, kitchen update in 2021, in unit washer/dryer combo, full furniture package included- just to name a few. This unit must be seen to be appreciated. It is currently positioned in the rental program, but can be removed if desired. Pick your desired lifestyle- keep it all to yourself or earn some income to help pay for your investment. Harbor Towers is well taken care of and well managed. Onsite management, security and well funded reserves make this complex a true winner. This unit also has a covered carport spot that is included in the purchase. Don't wait on this opportunity- these types of units don't come to market very often. Schedule your private showing today!

5855 Midnight Pass Road Unit 605, Sarasota

8701 Midnight Pass Road Unit 304A, Sarasota
$649,000
2 Beds ⋅ 2 Baths ⋅ Turtle Bay SubDv. ⋅ 34242 Zip Code
Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, this spacious condo blends modern coastal luxury with vibrant island living. Wake up to spectacular sunrises over the Intracoastal from your private, enclosed lanai, and wind down with sunsets via deeded beach access directly across the street. The generous primary suite features a walk-in closet, and a private entrance to the lanai. An in-unit laundry room includes a full-size washer/dryer and extra storage—a rare luxury on the Key! Additional upgrades include hurricane-impact windows to perfectly frame the water views. One of the most valuable features is the private, oversized 1-car garage providing secure parking and ample gear storage. Pet-friendly Turtle Bay offers premium amenities: brand-new boat docks/slips (just $300/year and you can add your own hoist), an updated fishing pier, kayak launch/storage, heated pool/spa, lighted tennis/pickleball courts, shuffleboard, clubhouse, and grilling area. Enjoy maintenance-free ease with on-site management, secure entry, and elevators. Leave your car behind and take the free trolley to nearby Siesta Village, South Village, or Point of Rocks snorkeling. Just minutes to Stickney Point Bridge and 20 minutes to downtown Sarasota. Perfect as a full-time residence, seasonal escape, or a great investment income opportunity.

8701 Midnight Pass Road Unit 304A, Sarasota

9393 Midnight Pass Road Unit 205, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
This beautifully renovated 2-bedroom, 2-bath condominium overlooking the bay was freshly painted on 9/8/2026 and is truly move-in ready. Turnkey furnished with an open kitchen featuring granite countertops, stainless-steel appliances, and solid-wood cabinets. The thoughtfully reconfigured layout is ideal for entertaining or relaxing while taking in spectacular views of the bay and nature preserve. Both bathrooms have been nicely remodeled, with tile flooring throughout, recessed lighting, and solid-wood interior doors. Wake each morning to breathtaking sunrises from your bed with a cup of coffee or tea. The spacious air-conditioned lanai, with full-width sliding glass doors, is perfect for watching dolphins and manatees, boaters and kayakers, or simply enjoying a good book. In-unit washer and dryer plus a separate lower-level storage area for beach chairs, fishing gear, golf equipment, and more. Simple paradise! *** THE POINTE is a pet-friendly gated community that offers the best of both worlds — activity and exercise alongside peace and tranquility. Surrounded by water on three sides and set on 5+ acres of prime waterfront, residents enjoy boat docks with electricity and water, outdoor walkways to each unit, a heated outdoor lap pool, spa, sauna, kayak/canoe/SUP launches, tennis and pickleball courts, dog walk, open-air gazebo with BBQ grills, clubhouse, entertaining/party rooms, fitness centers in each building, a non-smoking environment, butterfly garden, and more. Advantageously located near fine and casual dining, Turtle Beach, shopping, coffee shops, nightlife, entertainment, Siesta Key Beach, a full-service marina, public transportation, and everything else this island paradise has to provide A rare opportunity to own a true piece of Siesta Key.

9393 Midnight Pass Road Unit 205, Sarasota

1130 W Peppertree Lane Unit 118, Sarasota
$670,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Live the Siesta Key lifestyle! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect combination of island living, rental potential, and resort-style amenities. Ideally situated in the desirable Gulf-side community of Peppertree, this second-floor residence is just a short stroll from the tennis and pickleball courts, heated pools, and Siesta Key’s private-access beach. From the moment you arrive, you’ll appreciate the peaceful setting and tranquil views overlooking one of Peppertree’s picturesque ponds. The condo has been thoughtfully updated with all new impact windows, renovated kitchen and bathrooms, and updated flooring, creating a comfortable and inviting beach retreat. The spacious primary bedroom easily accommodates a king-size bed and features a walk-in closet. The home is offered turnkey furnished, making it ready to enjoy immediately or continue as a seasonal rental. It has consistently generated rental income during peak season, while also providing the flexibility to enjoy it personally during the off-season. Additional features include a full-size washer and dryer, newer A/C installed in 2019, a private storage unit conveniently located just outside the back patio, and a dedicated parking space. Peppertree is truly a destination within Siesta Key, offering direct Gulf-to-Bay access, a private fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ grills throughout the community, beach chairs, car wash areas, and on-site management with a rental program. High and dry with no storm damage, this exceptional condo offers the opportunity to own your own piece of paradise on world-famous Siesta Key. Whether you’re looking for a personal beach getaway, an investment property, or the best of both, this inviting Peppertree residence is ready to welcome you home.

1130 W Peppertree Lane Unit 118, Sarasota

6157 Midnight Pass Road Unit G11, Sarasota
$399,000
2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Sarasota

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