Siesta Key Homes with Association Recreation - Owned Community Features

Siesta Key Homes with Association Recreation - Owned Community Features

Welcome to Siesta Key, Florida, a picturesque barrier island nestled in Sarasota County, renowned for its powdery white sand beaches and vibrant coastal lifestyle. This tropical paradise is not just a vacation destination; it’s a community where residents enjoy a unique blend of relaxation and recreation.

Siesta Key is celebrated for its stunning Siesta Beach, consistently ranked among the best in the United States. The island offers an array of outdoor activities, from kayaking and paddleboarding to biking along scenic trails. The warm Gulf waters provide the perfect backdrop for swimming, fishing, and sunbathing, making it an ideal locale for both adventure seekers and those looking to unwind.

When it comes to real estate, Siesta Key boasts a variety of homes that cater to diverse lifestyles. Many properties are part of association recreation-owned communities, which enhance the living experience with a wealth of amenities. Residents can enjoy access to well-maintained pools, tennis courts, and clubhouses, creating opportunities for socializing and fostering a sense of community. These associations often organize events and activities, ensuring that neighbors become friends and creating a welcoming atmosphere.

With its charming boutiques, delightful dining options, and vibrant nightlife, Siesta Key offers a perfect blend of leisure and excitement. Whether you’re seeking a seasonal retreat or a permanent residence, Siesta Key’s homes with association recreation-owned features provide the ideal setting for a fulfilling coastal lifestyle. Embrace the beauty and warmth of this enchanting island, where every day feels like a vacation!

Newest Siesta Key Homes with Association Recreation - Owned Community Features

$1,325,000
2 Beds ⋅ 2 Baths ⋅ Siesta Breakers SubDv. ⋅ 34242 Zip Code
Welcome to the ultimate Siesta Key getaway at Unit 612 in Siesta Breakers! This beautifully updated penthouse is completely move-in ready and offered TURNKEY FURNISHED—just bring your sunglasses, swimsuit, and sense of adventure! Light, bright, and stylish, this fabulous residence offers gorgeous beach and pool views from the living room and screened-in patio. Spacious rooms, two oversized walk-in closets, and the convenience of an interior washer and dryer add to the great layout. The open kitchen and well-designed floor plan create the perfect setting for entertaining family and friends or relaxing after a sun-filled day at the beach. And when you’re ready to let the property work for you, Siesta Breakers permits weekly rentals and features an on-site management and rental office to help maximize rental opportunities. This gated, beautifully landscaped beachfront community sits directly on world-famous Crescent Beach and offers a fabulous lineup of amenities, including a sparkling pool, lighted pickleball and tennis courts, updated clubhouse, and deeded beach access. Just across the street, enjoy dining, shopping, and a full-service marina with boat rentals. Popular Siesta Key South Village is only steps away with local favorites such as Captain Curt’s Crab & Oyster Bar and a full-service grocery store. Need to stay connected? The updated clubhouse provides a convenient space for an uninterrupted Zoom meeting or conference call. Current building renovations are enhancing the community and offering peace of mind. The free Siesta Key trolley providing easy access to everything the island has to offer and you may find yourself happily ditching the car altogether. This is coastal Florida living at its most carefree, convenient, and fun—come experience your own slice of paradise on Siesta Key!

6480 Midnight Pass Road Unit 612, Sarasota
$700,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Virtually Staged. Experience the world renowned beaches of Siesta Key in this rarely available first floor luxury condominium steps away from your private deeded beach access. Conveniently located to Siesta Key’s south bridge, accessing the mainland, shopping in the village and access to nearby restaurants and stores is a breeze. Take the free public transport available to Siesta Village or head to Turtle Beach. Arrive home to a tastefully decorated unit with peaceful courtyard lake views. Entertaining and sharing a meal is an event with this updated chef’s kitchen. The enclosed lanai invites you for a cup of coffee, a book or contemplation. The primary suite features wood flooring, a true retreat like en-suite bath and upscale built-ins for the closet. Have peace of mind with impact windows and a new HVAC system installed 2025. There is plenty to do without going to the beach. Two heated pools, hot tubs, pickleball, tennis, fitness, fishing dock, library, beachside restrooms and more.

6265 Midnight Pass Road Unit 102, Sarasota
$1,400,000
3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
A TRUE 3-bedroom condo residence in desirable Casarina, a premier building positioned directly on the quartz white sands of #1 Siesta Key beach and the Gulf of Mexico. Step into this beautiful spacious residence and experience the flow of this open floor plan conducive to daily living, entertaining and accommodating family and friends. Sold turnkey furnished, this residence boasts impact windows & sliders providing security and protection, large ceramic floor tile throughout perfect for beach living and rich new carpet in the primary bedroom. The updated kitchen is stunning boasting neutral cabinetry, quartz countertops, stainless Jenn-Air appliances, Fisher & Paykel double dishwasher, quartzite island & breakfast bar, instant hot water faucet & 3 spacious pantries. The primary bathroom was updated in 2026 with quartzite countertops and upgraded dual vanities. Custom wood closet organizers are featured in all the bedrooms and an electric fireplace in the living room. The A/C was replaced in 2025, tankless water heater in 2023 and new screened lanai. Casarina is a secure building which has just undergone a complete building renovation & infrastructure. It offers an onsite manager and is fully funded with a 10-year capital plan and no special assessments. Besides the powder-white sand beach, experience tropical living on 7 acres of refreshed lush Florida landscaping, large refurbished heated pool and spa, cabana with outdoor kitchen & dining area, new poolside pergola with seating, 2 grilling areas, sunset decks, gas firepit with Adirondack chairs, resurfaced & lighted tennis court, 2 pickle ball courts, basketball hoop, fitness center, and social room/library. This condo offers secure under-building garage parking with an adjacent storage closet #5. The building renovation & infrastructure within the past two years includes a new reengineered resilient roof, new electrical and fire alarm systems elevated to the 2nd floor, new raised backup generator, new secured A/C units, multiple custom flood-prevention panels/dams, new ground water pump infrastructure, relined plumbing pipes, and refurbished elevators. Minutes to Siesta Village, shopping, restaurants and the culture of downtown Sarasota! So come on down and enjoy Florida living!

5880 Midnight Pass Road Unit 307, Sarasota
$575,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Welcome to this gorgeous WATER FRONT condo in desirable Midnight Cove II on beautiful Siesta Key! This coastal designed, TURNKEY furnished 2 bedroom beauty is move-in ready.. just bring your bathing suit and a toothbrush and you are off to the beach with its deeded beach access or hop on your boat , (docks subject to availability to rent for 100.00 a week) just steps away! Huge glass sliding doors open to the screened and tiled lanai with a stunning and expansive view of the inter-coastal waterway and south bridge. It's your private birds eye view to watch boats, dolphins, birds and all the abundant nature in your own little piece of paradise! Kitchen is updated and charming with granite counters, soft close cabinets and drawers, a coffee bar and eat-on counter, all open to the tropical views and updated tiled living areas. Bathrooms are stylish with a newly tiled walk-in shower and raised vanities. Condo has a convenient laundry closet with washer and dryer, and an outside storage closet with plenty of room for your sports equipment and beach toys. If you are looking for a rental investment, it may be leased on a weekly basis and offers an onsite management company. The amenities are top-notch and include a heated pool, clubhouse, deeded beach access, direct inter-coastal waterway access, fishing, boat docks, basketball court, tennis/pickle ball courts, grilling areas, and kayak storage. New roof 2025. Location of Midnight Cove II is sought after...walking distance to the local market, famed restaurants and bars, and shopping. Also it's close to pop over the bridge to the mainland to enjoy the arts scene, downtown and all Sarasota has to offer! Or... jump on the free trolley.. access just outside of the community and it takes you to the bustle of the Siesta Village or to the South end of the island to Turtle Beach! So much to explore and enjoy in your new Siesta Key home! ISLAND LIFE at it's FINEST!

1900 Cove Ii Place Unit 127, Sarasota
$1,795,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an impressive rental history—all within one of Siesta Key’s most recognizable beachfront communities. Beyond its appeal as a personal beachfront escape, #809 offers an established rental history. The residence averages more than $80,000 in annual gross rental income (2024 – 2026), with bookings extending through year-end, offering a compelling opportunity for buyers seeking to combine personal enjoyment with income potential. Inside, the 1,271-square-foot residence has been thoughtfully reimagined with a fresh coastal aesthetic, luxury vinyl wood-plank flooring throughout, custom architectural ceiling treatments, and an open floor plan that keeps the Gulf firmly in view. The designer kitchen is both polished and functional, featuring granite countertops, custom Shaker-style cabinetry, stainless steel appliances, and a refrigerator cleverly concealed behind coordinating custom cabinet panels. The kitchen opens naturally to the dining area, where a built-in banquette creates an inviting gathering space beneath a dramatic coffered ceiling accented by designer lighting and naturally stained solid-wood beams. Beyond, the Gulf-front living room is framed by walls of glass, drawing your eye directly toward the water and opening to the screened terrace. The terrace is where the Siesta Key lifestyle truly takes center stage. Stretching across the Gulf-facing side of the residence, this generous outdoor living space provides a front-row seat to turquoise water, passing boats, and spectacular Gulf sunsets. A desirable split-bedroom floor plan provides privacy for owners and guests, with both bedrooms positioned to enjoy Gulf views and direct access to the screened terrace. Each bedroom also features a walk-in closet with built-in organization. The primary suite is complemented by a beautifully renovated en-suite bath with dual sinks, granite countertops, extensive built-in linen storage, and an oversized walk-in shower with bench seating. The second bath is also well appointed with newer cabinetry, stone counters and a tub/shower combination. Crystal Sands is an iconic Siesta Key beachfront community distinguished by its classic architectural presence and exceptional location directly on the Gulf of Mexico. Residents and guests enjoy a heated community pool, gated entry, elevators, recreation facilities, covered and guest parking, and direct access to the beach and Gulf. The residence also includes one covered carport space. And when you are ready to venture beyond the beach, some of Siesta Key’s favorite destinations are close at hand. Head north to Siesta Key Village for its lively collection of restaurants, boutiques, cafés, and nightlife, or south toward Crescent Beach, Point of Rocks, and the restaurants and conveniences surrounding Stickney Point Road. The Siesta Key trolley makes exploring the island especially easy, with service along the Key connecting beaches, dining, shopping, and Siesta Key Village.

6300 Midnight Pass Road Unit 809, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Turnkey and ready for its next chapter, this spacious residence in the curve of Harbor Towers Yacht & Racquet Club is one of the largest floor plans in the building, featuring a split layout with each bedroom offering its own private bathroom. Sold completely furnished, this unit makes it effortless to fly or drive down and start enjoying it immediately, or begin renting it out right away. A rare find: existing washer/dryer electric hookups are already in place beneath the kitchen counter, a feature the building no longer permits for new installations. There's also a washer and dryer room located on the second floor just a few doors down. Picture the perfect Florida day: morning coffee on your enclosed patio overlooking the peaceful pond, then a match on the on-site tennis courts before laying out by the beautiful pool, both with views over the dock and water. Hop the trolley or take a short drive to the rose quartz sand beaches of Siesta Key, then wind down with happy hour and live music in Siesta Key Village. This unit can be rented short-term with a two-week minimum, and owners have the flexibility to use the community's on-site property management or bring in their own. Just three minutes to Siesta Key's world-famous beaches and five minutes to the shops and restaurants of Siesta Key Village, this is the perfect Florida lifestyle. Schedule your private showing today. Buyer to verify HOA rules regarding laundry hookups, boat slip rental terms, property management options, and rental restrictions.

5855 Midnight Pass Road Unit 222, Sarasota
$874,900
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
ENDLESS POSSIBILITIES ON SIESTA KEY. Welcome to 19 Whispering Sands Drive, Unit 201, an exceptional opportunity to create your own Gulf Coast retreat in one of Siesta Key’s most established beachfront communities. Whether you choose to enjoy the residence as it is, renovate it over time, or completely reimagine the interior to reflect your own style, the possibilities are nearly endless. For buyers who want a more turnkey path, a renovation package can also be made available to help transform the residence into a beautifully updated coastal home. What cannot be recreated is the setting. Whispering Sands offers approximately 800 feet of private quartz-sand beach directly on the Gulf, two heated swimming pools, a beachside Tiki Hut and grills, fitness facilities, kayak and canoe storage, shuffleboard and beautifully maintained grounds. The community continues to invest in its future, with the Clubhouse and exclusive Tower Lounge undergoing renovation and improvements throughout the property. Here, the lifestyle begins outside your door. Spend mornings along the Gulf shoreline, afternoons by the pool and evenings watching Siesta Key’s celebrated sunsets. Siesta Key Village is just moments away, putting restaurants, boutiques, entertainment and island life within easy reach. Make it your own, renovate it with our available design and renovation package, or explore its rental possibilities subject to association requirements. The location is already extraordinary. The next chapter is yours to create.

19 Whispering Sands Drive Unit 201, Sarasota
$479,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Beautifully Updated One-Bedroom Condo on Siesta Key Enjoy the best of island living in this beautifully updated one-bedroom, one-bath condominium on Siesta Key. This inviting unit has been completely updated and features all-new appliances and a new water heater, offering a fresh, move-in-ready interior. The community offers an impressive selection of on-site amenities, including: • Two swimming pools • Tennis courts • Four shuffleboard courts • Beach access Located on beautiful Siesta Key, this condo offers the perfect combination of comfort, convenience, and the relaxed Florida lifestyle. Whether you’re looking for a full-time residence, seasonal getaway, or investment opportunity, this property provides an excellent opportunity to own a piece of paradise just steps from the beach.

6006 Midnight Pass Road Unit 60, Sarasota
$729,500
2 Beds ⋅ 2 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code
Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gulf of America, with a 5-minute walk down community path. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. One bedroom has a 1 king bed and one with a 1 queen bed, queen sofa bed in living room. Cozy Electric Fireplace, Heated Pool, Area for lounging in the sun, dock area for fishing, Tiki Hut with chairs & charcoal grills. This fabulous property offers a comfortable and inviting space for guests- enclosed lanai and a large private deck overlooking the Bay with a gas grill and outdoor furniture. You'll find all the essentials you need, including 2 yr. old AC, hair dryer, Wi-Fi, an iron, coin laundry, beach chairs, wagon and umbrella, beach towels included in this turn-key sale! Move in and enjoy your new purchase. Laundry hook-ups but there are coin laundry machines on the 1st floor. Pets are not allowed. Minutes from Restaurants, Shopping, Entertainment, Grocery Store and Downtown Siesta Key Village. Public Stop for the Trolly is steps from the Condo Entrance! The views are exceptional of the ICW and bay as this the bayfront unit on the second floor, the only one with the large patio. This unit comes with a one car garage that only a few units are lucky enough to have. This two-bedroom unit has a deluxe bathroom and a half bathroom as well. Nice kitchen with granite tops and island L bar seating. Dinig table next to kitchen for those family dinners to make memories at. There is a community marina to bring your boat and enjoy this true Florida Beach and Bay lifestyle!!

5955 Midnight Pass Road Unit 21E, Sarasota
$1,099,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi, thermostat keyless entry! Your new condominium will be sold turnkey furnished, nothing to do except move in. Open floor plan great for entertaining. A super beverage cooler has been installed in the kitchen. You will find pull-outs and soft close doors & drawers. Two full sized beds in the guest room, and the main suite has gulf views, double vanities for convenience. Both bathrooms have walk-in showers. This is a split plan as well. What I really want you to see are the community grounds… the condo is fabulous, and this community is spectacular!!! You can search the state of Florida... no other community can compare itself to Gulf & Bay. Plus, END UNIT condos are the best - nothing compares to having an END UNIT. Gulf & Bay has 2 pools, new fitness center just steps away from the elevator plus saunas, tennis & PICKLEBALL courts, basketball, electric car charging stations, clubhouse, indoor hot tub. Another cool item is the complex is mapped out with its own app. Owners can easily navigate in and out of the grounds with your phone. No more fobs. Gulf & Bay is great for rental income. If you want rental income, this condo has it for 2027. Rentals must be a 30-day minimum 12 times a year. I know it just got better, right? Want to head to the village? Just hop on the free trolley out of the gates and head to the village for dinner and shopping. The condo is easy to show. Don’t miss seeing this community and condominium… the search is over... get here before this opportunity is gone! here are the dates booked for this coming season! Feb 1, 2027-Feb 28, 2027 27 nights $8,913.00 Mar 1, 2027-Mar 29, 2027 28 nights $10,052.00 Jan 1, 2027-Jan 31, 2027 30 nights $6,760.10 _____________ $25,725.10 As of 8-10-2026

5770 Midnight Pass Road Unit 301, Sarasota
$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
Start Your Search