Sarasota/Crescent Beach/Siesta Key Homes with Pool Amenities

Sarasota/Crescent Beach/Siesta Key Homes with Pool Amenities

Welcome to the enchanting region of Sarasota, specifically the picturesque enclave of Crescent Beach on Siesta Key, Florida. This idyllic coastal paradise is renowned for its powdery white sands and stunning turquoise waters, making it a perfect retreat for beach lovers and outdoor enthusiasts alike. Nestled on the Gulf of Mexico, Siesta Key boasts a vibrant community that offers an array of dining, shopping, and recreational activities, all while basking in the warm Florida sun.

Crescent Beach, known for its serene atmosphere and breathtaking sunsets, is a hidden gem that attracts visitors and residents seeking tranquility and natural beauty. The area is not only a haven for beachgoers but also offers opportunities for kayaking, paddleboarding, and exploring the nearby nature trails. With its charming local shops and delightful restaurants, you’ll find everything you need to enjoy a laid-back lifestyle.

When it comes to real estate in this stunning region, homes featuring pool amenities are a standout choice. Imagine stepping into your own private oasis after a day at the beach, where you can unwind in your sparkling pool while savoring the gentle ocean breeze. Properties in Crescent Beach and Siesta Key often come equipped with luxurious outdoor spaces, perfect for entertaining friends and family or simply soaking up the sun.

Whether you’re looking for a vacation getaway or a permanent residence, the homes in this area offer the perfect blend of comfort and coastal charm. Discover your dream home in Sarasota’s Crescent Beach, where every day feels like a vacation!

Newest Sarasota/Crescent Beach/Siesta Key Homes with Pool Amenities

$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
$625,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
SUNSETS, SUNSETS, SUNSETS! Experience the Siesta Key lifestyle in this turnkey furnished 5th-floor residence located in the highly desirable Peppertree Bay community. Situated on the Bayside, this 2-bedroom, 2-bath condo offers panoramic views of Siesta Key and spectacular Florida sunsets, along with private deeded beach access just across the property. Tile flooring flows throughout the residence, while the custom kitchen features granite countertops, a tile backsplash, abundant cabinetry, and brand-new stainless steel appliances. The open-concept dining and living areas extend into the enclosed lanai, creating additional space to relax, entertain, and enjoy the beautiful views. Additional features include a newer (2024) HVAC system, a new 80 gallon hot water heater, an in-unit washer and dryer, generous storage, and convenient under-building parking. Offered turnkey furnished, this residence is ready to enjoy from day one. Peppertree Bay is a sought-after Gulf-to-Bay community offering an exceptional array of amenities, including private deeded beach access, two heated swimming pools, two clubhouses with full kitchens, tennis and pickleball courts, a fitness center, fishing pier, BBQ grills, picnic areas, and an active social calendar in season. Ideally located on Siesta Key with easy access to Siesta Key Village, enjoy nearby dining, shopping, live entertainment, and everything Sarasota offers. Whether you're searching for a full-time residence, seasonal retreat, or investment property, this condo delivers the location, amenities, and lifestyle that make Siesta Key so desirable.

1200 E Peppertree Lane Unit 505, 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
$625,000
2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
Embrace the Siesta Key lifestyle at Tortuga Beach Club! This spacious 2-bedroom, 2-bath residence offers 1,650 square feet of living space in an intimate 77-unit Gulf-front community on the desirable south end of Siesta Key. From relaxing days along the private beachfront to unforgettable sunsets over the Gulf of Mexico, Tortuga offers the coastal lifestyle you've been dreaming of. Step inside and discover a light and inviting split-bedroom floor plan with an enclosed lanai that extends the living space and provides the perfect spot to relax and unwind. The spacious kitchen features wood cabinetry, granite countertops, abundant storage and a convenient pass-through breakfast bar overlooking the living area. A separate dining room just off the kitchen provides additional space for entertaining family and friends. The primary suite offers generous closet space, with the washer and dryer conveniently located within the primary closet. A new A/C system adds comfort and peace of mind. Tortuga Beach Club offers an impressive array of amenities designed for enjoying the best of island living. Spend your days on the private Gulf-front beach, take a swim in the heated indoor/outdoor community pool, relax in the sauna, or gather with friends on the sun deck featuring grills and seating areas. The community clubhouse offers a kitchen, library and entertainment space, while tennis and pickleball courts are conveniently located across Midnight Pass Road. Boating enthusiasts will appreciate access to boat slips across the street on the bay, with slips currently available for annual rental by application. A community laundry facility provides additional convenience when needed. The residence also includes covered parking conveniently located near the building entrance and elevator, making loading and unloading a breeze. The location completes the package! Enjoy close proximity to Turtle Beach, where you can spend the day along the shoreline, launch a kayak or simply soak up the laid-back atmosphere of south Siesta Key. You're also near some of the island's favorite dining destinations, including Ophelia's on the Bay, Turtles Restaurant and other nearby waterfront and casual dining options. Siesta Key Village, shopping, entertainment and the world-famous quartz sands of Siesta Beach are just a drive up the island. Whether you're searching for a full-time island residence or your own Siesta Key getaway, this spacious Tortuga Beach Club condominium brings together private Gulf-front beach access, boating, resort-style amenities and an exceptional south Siesta Key location. Spend your days enjoying the water and your evenings watching spectacular Gulf sunsets this is Siesta Key living at its best!

8710 Midnight Pass Road Unit 203B, 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
$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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