Siesta Key Homes with Pool Amenities

Siesta Key Homes with Pool Amenities

Welcome to Siesta Key, Florida – a slice of paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant community, and laid-back lifestyle. This charming barrier island is not just a destination; it's a lifestyle. With its powdery white sands and crystal-clear waters, Siesta Key is consistently ranked among the best beaches in the United States, making it a haven for sun-seekers and beach lovers alike.

Beyond its breathtaking shoreline, Siesta Key boasts a unique blend of quaint shops, delightful eateries, and lively nightlife, all infused with a warm, welcoming atmosphere. Whether you’re strolling along Ocean Boulevard or enjoying a sunset at Siesta Beach, the island exudes a sense of tranquility that captures the hearts of residents and visitors alike.

For those seeking their dream home in this idyllic locale, Siesta Key offers an array of properties featuring luxurious pool amenities. Imagine unwinding in your private oasis, soaking up the sun by your sparkling pool after a day of beach adventures. These homes are designed for relaxation and entertainment, providing the perfect backdrop for family gatherings, barbecues, or simply enjoying the Florida sunshine.

With a variety of architectural styles and sizes, from charming beach cottages to modern estates, Siesta Key has something for everyone. Whether you’re looking for a vacation retreat or a permanent residence, the allure of a home with pool amenities in this picturesque setting is undeniable. Dive into the Siesta Key lifestyle and discover your perfect home today!

Newest Siesta Key Homes with Pool Amenities

$400,000
2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code
Your Siesta Key Lifestyle Awaits — The Time to Own Is Now! Welcome to one of Sarasota’s most sought-after coastal destinations, where the beauty of Siesta Key is right outside your door. This completely updated ground-floor residence captures the true essence of coastal living with a soft, neutral palette and a relaxed, welcoming atmosphere. This property sets itself apart from all the others—it makes you feel right at home at the beach the minute you arrive. The spacious bedrooms provide plenty of room for family and guests, with the oversized guest bedroom large enough to accommodate two full-size beds, comfortably sleeping four. The beautifully refreshed kitchen features new appliances, quartz countertops, updated cabinetry, and a new tile backsplash that perfectly complements the home’s coastal-inspired design. Extend your enjoyment outdoors in the enclosed lanai, offering privacy and a comfortable space to enjoy year-round. There is also the possibility of adding a paver extension to the lanai, creating even more outdoor living space for relaxing and entertaining. A convenient in-unit laundry closet with washer and dryer adds to the ease of everyday living, while storm windows and doors provide added peace of mind. And then there’s the lifestyle! Spend your days enjoying the world-famous sands of Siesta Key Beach, explore the beauty of Selby Gardens, shop and dine at St. Armands Circle, or head into downtown Sarasota for its incredible restaurants, arts, culture, and waterfront attractions. And don’t miss one of the area’s most anticipated fall events—the Siesta Key Crystal Classic Sand Sculpting Festival. Come be part of the fun, experience the incredible artistry, and enjoy yet another reason why life on Siesta Key is so special. The time is now to make this coastal retreat your own and be ready for the 2027 season. Whether you’re looking for a full-time residence, a beach escape, or your own piece of the Siesta Key lifestyle, this beautifully updated home offers something truly special. Come see for yourself why this one feels different. Your beach lifestyle begins the minute you arrive.

116 Vista Hermosa Circle Unit 108C, Sarasota
$839,900
2 Beds ⋅ 3 Baths ⋅ Gulf Haven SubDv. ⋅ 34242 Zip Code
RARELY AVAILABLE CONDO IN GULF HAVEN ON SIESTA KEY BEACH! This nicely updated 2-bedroom, 2.5-bath unit in the highly desirable Gulf Haven community won't be on the market for long. With limited availability in this intimate beachfront community, you have a special opportunity to be a part of the Siesta Key community. This unit offers comfortable coastal living with a practical layout and inviting spaces. With two bedrooms and two-and-a-half baths, there is plenty of room for owners and guests to relax and enjoy everything island living has to offer. Private beach access is one of the standout features of Gulf Haven, giving you the ability to enjoy the soft white sands and beautiful Gulf waters. After a day at the beach, take a refreshing dip in the inviting community pool. A covered carport that is connected to the unit provides convenient, protected parking—another valuable feature on Siesta Key. The location puts you close to the best of Siesta Key and Sarasota. Enjoy easy access to Siesta Key Village, local shops and restaurants, boating, and more. When you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering exceptional dining, shopping, arts, entertainment, and cultural attractions. Whether you're looking for a vacation home, seasonal retreat, investment property, or full-time residence, this rarely available Gulf Haven condo offers an exceptional way to enjoy the Sarasota Gulf Coast lifestyle. Updated interiors, private beach access, a community pool, covered parking, and a location close to it all make this a property worth seeing. Opportunities to own in Gulf Haven don't come along often—come experience the Siesta Key lifestyle for yourself.

5860 Midnight Pass Road Unit 23, 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
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Sara Sea SubDv. ⋅ 34242 Zip Code
SHORT TERM RENTAL ALLOWED. Island living at 6796 Sarasea Circle, ideally located near Point of Rocks on Siesta Key. This spacious 3-bedroom, 3-bath, three-story residence offers 1,890 SF of living area plus an additional 333 SF of air-conditioned studio/efficiency space, for a total of 2,223 SF of air-conditioned space. Additional features include an oversized two-car garage, Large outside balcony/deck 16.6.x 7.7 PLUS private beach access and private heated pool access, all just a short walk from several restaurants like the local favorite "Lenny'z" Pizza and Island Bar , shops and entertainment on South Siesta Key. The main living level features an open floor plan with volume ceilings, kitchen, dining area and family room with fireplace. A oversized balcony provides additional outdoor living and entertaining space. The upper level includes the primary suite with ensuite plus a large second bedroom and full bathroom. The downstairs third bedroom and bathroom can also function as a private in-law suite or studio efficiency, complete with kitchenette and separate entrance—providing flexibility for guests, extended family or additional living space. A private fenced courtyard adds another outdoor area. Recent improvements include a complete NEW A/C system in 2026, metal roof in 2023 and new window coverings. All appliances, including washer and dryer, are included. Average power bill around $180

6796 Sarasea Circle Unit 3, 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
$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
$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
$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 2,165-square foot 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 and tankless water heater in 2023. 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
$449,500
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable Siesta Harbor 55+ community is clean, bright, inviting, and ready for its next owner. Just steps from the soft, powdery sands of Siesta Beach, this is the perfect opportunity to enjoy the laid back island lifestyle you've been dreaming about. From the moment you walk in, you'll appreciate the fresh, coastal feel and thoughtful updates throughout. The residence features beautiful luxury vinyl flooring, a renovated kitchen, updated bathrooms, a brand new vanity in the guest bath, and new and newer appliances. The open and comfortable floor plan is filled with natural light and designed for easy everyday living. One of the true highlights is the spacious all seasons lanai, where you can sit back, relax, and take in the fantastic waterfront views. Watch boats cruise along the shimmering saltwater canal as you enjoy your morning coffee or unwind with a glass of wine in the evening. The canal leads directly to the Intracoastal Waterway and Gulf of Mexico, creating a beautiful backdrop and a constant reminder that you are living on Siesta Key. Siesta Harbor is an active and welcoming 55+ community with an incredible selection of amenities and activities. Enjoy the heated pool and spa, fitness center, sauna, clubhouse, shuffleboard courts, private Intracoastal pier, and a wonderful social calendar filled with community events and activities. Fishing enthusiasts will love the private waterfront pier, while boaters have the opportunity to lease dock space on a first come, first served basis. Residents also enjoy deeded beach access through Crescent Arms, beautifully maintained tropical grounds, on site management, private storage, and same floor laundry. With the free trolley stop conveniently located just outside the community, Siesta Key Village, local shops, restaurants, and entertainment are all easily accessible. The South Bridge provides convenient access to mainland Sarasota, downtown, and the area's many cultural attractions. Whether you're looking for a full time home, a seasonal escape, or your own island retreat, this residence offers an incredible combination of location, updates, waterfront views, amenities, and lifestyle. Clean, freshly painted, beautifully updated, and ready to enjoy, this is a fantastic opportunity to own a little piece of paradise on Siesta Key. Come see why life is better on the Key!

1300 N Portofino Drive Unit 103, Sarasota
$399,000
2 Beds ⋅ 2 Baths ⋅ Cozy Cove SubDv. ⋅ 34242 Zip Code
Opportunity knocks on Siesta Key at $399,000, and the seller is paying your first six months of association fees.Located within Cozy Cove, an intimate six-residence waterfront community on the quiet southern end of the island, this 2-bedroom, 2-bath single-level condominium offers a compelling entry point for the buyer ready to create something of their own. The residence is clean and functional today, but its largely original interior presents the opportunity for a full renovation and repositioning. Buy now, renovate through the off-season, and have it ready for Season 2027, whether your strategy is vacation rental, resale, or simply creating your own Siesta Key getaway. Cozy Cove offers weekly rentals, a waterfront pool, brand-new docks along Blind Pass, and even a glimpse of the Intracoastal from the residence, all just minutes from Turtle Beach. Whether the plan is to hold, rent, renovate and resell, or some combination of the three, opportunities to enter Siesta Key at this price point are increasingly hard to find.

9034 Midnight Pass Road Unit 6, Sarasota
$545,000
2 Beds ⋅ 2 Baths ⋅ Beachaven SubDv. ⋅ 34242 Zip Code
Welcome to your tropical retreat at Beachaven, a highly desirable beachfront community on Siesta Key! This turnkey charming 2-bedroom, 2-full-bathroom villa spans 813 sq. ft., offering the ultimate beach escape. Nestled just steps from the pristine powdery white sands and crystal-clear waters, this villa provides unparalleled access to sun-soaked beaches and breathtaking Gulf views. Enjoy your morning coffee or unwind in the evenings on your private lanai, where you can immerse yourself in the sounds of the ocean and the vibrant coastal atmosphere. Beachaven features a heated pool overlooking the ocean, perfect for relaxing while soaking in the sun or enjoying a refreshing dip. The community boasts a unique monthly rental program, allowing you to generate rental income with minimal fees while maintaining the flexibility of using your villa as a personal getaway. This property is ideal for investors or those looking to offset ownership costs. Experience a relaxed lifestyle in this serene community, with easy access to Siesta Key Village, where you can explore boutique shops, delightful restaurants, and lively farmers markets. This villa is more than just a home; it’s a gateway to a vibrant coastal lifestyle. Don’t miss your opportunity to own a piece of paradise in this sought-after location!

5858 Midnight Pass Road Unit 13, Sarasota
$45,000
4 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code
Fractional Ownership. FRACTIONAL OWNERSHIP **GUARANTEED GULF FRONT DELUXE UNIT** Imagine a perfect family retreat every year for Memorial Weekend on world famous Siesta Key Beach! Why not let the Hyatt Vacation Club manage all your entertainment and luxury high-end. GULF FRONT WITH GULF VIEW accommodations! For local residents and all owners, enjoy the alternative lifestyle for two weeks a year with an additional float week. This year’s dates are May 22-May 29 and May 29 to June 5 in 2027. Enjoy the option of the Hyatt Vacation Club’s exchange program, reservation procedures, point values, and availability to change your family get-togethers! This floorplan offers a primary suite, a junior suite, a guest bedroom, and a den with a sleeper sofa. These units overlook the pool and beach; not all units do. The best part of Siesta Key is that you will not need a vehicle. Trolley, buses, golf carts are all available for Siesta Key transportation. For casual dining, fine dining, live entertainment every day, this is the destination everyone is discovering. Easy flights, easy drive! More details upon request. This is a great opportunity to act on at these exceptionally low prices!

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota
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