Homes With Pool For Sale In Siesta Key

2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code

Welcome to your slice of paradise on Siesta Key! This beautifully maintained two-bedroom, two-bath first-floor end unit offers a blend of comfort, convenience and coastal living with no stairs to climb and easy access throughout. Ideally just a short two-block stroll to world-famous Siesta Key Beach, you’ll enjoy powdery quartz sand that stays cool underfoot, even on warmest days. This well-maintained island condominium features a roomy layout and comes fully furnished, making it move-in ready or ideal as an income-producing rental. The generous screened lanai overlooks the peaceful marina, creating a spot to relax with your morning coffee or unwind at sunset. Boating enthusiasts will appreciate the sought-after deeded boat dock, providing direct water access to the Intracoastal Waterway. The private garage with overhead storage offers plenty of extra space for beach, fishing gear and more. Within the desirable Harbour Towne community, residents enjoy a host of amenities including a heated swimming pool, spa, tennis and pickleball courts, plus a welcoming clubhouse known for its friendly, social atmosphere. Whether you're seeking a seasonal getaway or investment opportunity, this condominium checks every box. Enjoy the laid-back Siesta Key lifestyle with dining, shopping and entertainment just minutes away, all while living near one of the world’s celebrated beaches.

1249 Dockside Place Unit 110, Sarasota

$4,995,000

8 Beds ⋅ 9 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.

336 Avenida De Mayo, Sarasota

$4,995,000

9 Beds ⋅ 8 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!

332 Avenida De Mayo, Sarasota

$5,390,000

6 Beds ⋅ 7 Baths ⋅ Mira Mar Beach SubDv. ⋅ 34242 Zip Code

Unlock a rare opportunity to own a high-performing nightly-rentable vacation property in the coveted Golden Triangle of Siesta Key—one of the most desirable short-term rental zones on the Key. This turnkey residence is already operating as a successful short-term vacation rental, offering immediate income with future bookings in place. Positioned just steps from Siesta Key Village and world-famous Siesta Beach, this property sits in the heart of the island’s premier tourism district, where nightly rentals are fully permitted and demand remains consistently strong year-round. Guests love the walkability, the proximity to dining and entertainment, and the effortless beach access—making this an ideal asset for investors seeking reliable occupancy and premium nightly rates. A luxurious Siesta Key retreat just steps from the beach, offering Gulf views, resort-style outdoor living, and high-end finishes throughout. With six bedrooms, 6.5 bathrooms, an elevator, multiple decks, a rooftop terrace, and an incredible pool with a slide, this home blends elegance with fun. Its unbeatable location—one minute to the beach and 3 minutes to Siesta Key Village—makes it ideal as a primary residence, vacation home, or high-performing investment property.

85 Avenida Messina, Sarasota

$2,200,000

5 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Price Reduced! Spacious island living, strong weekly rental income, and a prime north Siesta Key location come together in this beautifully maintained 5-bedroom, 3-bath furnished home just steps from beach access No. 1 at Shell Road on Big Pass. Built above base flood elevation of 11 feet, this property offers a valuable advantage on Siesta Key, along with the comfort, privacy, and usability today’s buyers are looking for. Fully gated and walled, the home sits on a generous lot surrounded by lush tropical landscaping, with an oversized 3-car garage and large paver driveway providing ample space for vehicles, beach gear, and a golf cart. Inside, the home offers large, open living spaces ideal for gathering and entertaining, featuring 12-foot ceilings, crown molding, arched openings, travertine flooring, and a spacious living room with gas fireplace. The kitchen includes stainless steel appliances, oak cabinetry, a breakfast nook overlooking the backyard oasis, and easy flow to the separate dining area and main living spaces. French doors open to a large terrace overlooking the tropical backyard, while an additional side terrace offers a private place to relax. The main-floor primary suite is a standout, offering direct terrace access, an oversized bedroom, two walk-in closets, and a luxurious en-suite bath with dual vanities, soaking tub, walk-in shower, and floor-to-ceiling travertine. Two additional bedrooms and a full bath are also located on the first floor, creating a functional and flexible layout. Upstairs, two generous guest bedrooms, a full bath, and a wet bar with beverage fridge provide an ideal retreat for visitors, with one bedroom opening to a private terrace overlooking the backyard. Designed for indoor-outdoor island living, the backyard is a true tropical oasis with mature landscaping, a heated saltwater pool with fountain, paver deck, large turf area, outdoor shower, and an exceptional tiki hut bar and outdoor kitchen complete with a built-in gas grill, two bar fridges, and porcelain countertops. An additional fenced side yard offers extra space for pets or outdoor enjoyment. Offered turn-key furnished, with a five-bedroom layout, generous lot size, multiple terraces, abundant storage, central vacuum, and expected 2026 rental income of $190,000. This home is an outstanding opportunity for those seeking a private Siesta Key retreat, income-producing investment, or both. Ideally located near world-renowned Siesta Key Beach and just a short drive to downtown Sarasota’s restaurants, shopping, and cultural attractions, this property offers the best of island living with convenience, comfort, and flexibility.

3508 La Paloma Avenue, Sarasota

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code

At the pinnacle of an intimate, gated community on world-renowned Siesta Key, this penthouse condominium offers a rare opportunity to enjoy sweeping bayfront living with breathtaking views stretching across the water to the skyline of Sarasota. Offered turnkey furnished, this beautifully maintained residence is ready for immediate enjoyment, whether as a full-time home or a luxurious island retreat. Inside, vaulted ceilings and tile floors enhance the light-filled interior, while plantation shutters add timeless coastal elegance throughout. The thoughtfully designed layout features two bedrooms with walk-in closets and two baths, including an oversized primary suite that provides a spacious and relaxing retreat. Near the dining area is a private den with sleeper sofa for extra guests. The kitchen features white wood cabinets with solid surface countertops and eat-in dining space. A wet bar just off the kitchen can be used as a dedicated coffee station or wine bar. The sunroom extends the living area, inviting you to unwind while enjoying spectacular sunset views over the bay. Go outside to enjoy one of the two covered front patios, ideal for morning coffee or evening breezes. The residence also includes the convenience of a private single-car garage, a desirable feature for island living. With only 50 residences, this gated waterfront community offers a rare sense of privacy and exclusivity. Residents enjoy an exceptional collection of amenities, including a resort-style pool and spa, three desired Har-Tru tennis courts, fitness center and community grilling area, all supporting the vibrant and social lifestyle the community is known for. The day dock and kayak launch provide direct access to the bay for fishing, paddleboarding, kayaking, or simply docking and enjoying the waterfront setting. Experience the best of Siesta Key penthouse living, where panoramic bay views, resort-style amenities and an active waterfront lifestyle come together in one extraordinary residence.

1280 Dolphin Bay Way Unit 504, Sarasota

$679,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opportunity for TURNKEY FURNISHED Residence with FULL WATER VIEWS throughout all Living Areas!..... Located in the Whispering Sands Community you will be able to WALK to the adjacent Village as well as ENJOY over 800' of PRIVATE deeded "white baby powder quartz sands" Beach Access; (2) Heated Pools; clubhouse, fitness center; beachside tiki and so much more in a true "residential neighborhood" setting. Bright & Spacious Open Floor Plan; Updated Kitchen and Baths with Quartz Countertops & Backsplashes; HURRICANE IMPACT SLIDERS open into an Expansive Lanai with Multiple Living Spaces---Perfect for listening to your favorite podcast or Enjoying Majestic Sunsets with Evening Cocktails----The Ultimate in the Siesta Key Lifestyle!

101 Whispering Sands Drive Unit 105, Sarasota

$1,600,000

3 Beds ⋅ 3 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code

Tucked inside the private enclave of Siesta Cove, this beautifully updated island home offers that rare blend of privacy, space, and an easy walk to world-famous Siesta Key Beach. Set on an oversized 0.35-acre lot, the property features 3 bedrooms, 2.5 baths, and more than 2,500 square feet of bright, open living space designed for both everyday comfort and effortless entertaining. Vaulted ceilings with exposed beam detail anchor the main living area, where expansive sliders open to a screened lanai and private saltwater pool framed by mature tropical landscaping. Porcelain tile runs throughout, creating a clean, cohesive feel that fits perfectly with relaxed island living. The kitchen is thoughtfully designed with stone countertops, stainless steel appliances, generous prep space, and a built-in wine refrigerator, flowing naturally into multiple living and dining areas. Whether you’re hosting friends after a beach day or enjoying a quiet evening at home, the layout simply works. The primary suite feels tucked away and private, complete with an updated bath featuring a rain shower and elevated finishes. Two additional bedrooms offer flexibility for guests, family, or a dedicated office space. Impact windows and doors provide added peace of mind, and the home did not experience water intrusion during recent hurricanes. Additional features include a fireplace for cooler winter nights, an interior laundry room, circular driveway, and attached two-car garage. Siesta Cove is ideally positioned between Midnight Pass Road and the Intracoastal Waterway, just a short stroll to the powder-soft quartz sands of Siesta Key Beach. Here, mornings start with beach walks, afternoons are spent boating or biking the island, and evenings wind down with sunset skies and dinner in the Village. This is not just a home — it’s the kind of island living people move here for.

5231 Siesta Cove Drive, Sarasota

$499,900

1 Beds ⋅ 1 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

THE VIEW, THE VIEW, Location, Location. This is IT! RESORT LIVING UNDER $500,000! EVERY AMENITY AT YOUR FINGERTIPS! BEAUTIFULLY APPOINTED, IMPRESSIVE ENTRANCE WITH WATERFALL, WALK INTO THE LUXURY APPOINTED HUGE FOYER--TURN KEY INCOME GENERATING VACATION HOME! STUNNINGLY SELECTED AND DESIGNED UNIT OVERLOOKING THE POOL AND VIEW OF INTRACOASTAL WATERWAY---DESIRABLE 2 WEEK RENTAL WHEN YOURE NOT HERE, BLOCK IT OUT WHEN YOU COME TO ENJOY AND RELAX! ON SITE RENTAL OFFICE TAKES CARE OF IT ALL! Experience the ultimate in luxury coastal living within the waterfront resort community of Harbor Towers Yacht & Racquet Club, one of Siesta Key’s most desirable gated waterfront communities. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis to provide modern comfort and elegant coastal style with a gorgeous view of the heated pool and outdoor awning for alfresco dining. Being sold turnkey furnished, this third-floor residence is decorated for immediate enjoyment as a full-time home, vacation getaway, or income-producing investment property. The stunningly renovated interior features hurricane-rated windows, a breathtaking quartz kitchen, vinyl plank wood floors and a stunning bathroom accented in gold. The open-concept living and dining area is filled with natural light, creating a bright and welcoming space ideal for relaxing or entertaining. Included is a washer and dryer, plenty of extra storage space directly across the hall and additional large washers and dryers located on each floor for larger items. Perfect for couples and extended stays, this retreat combines modern coastal finishes, large windows, and resort-style amenities just minutes from world-famous Siesta Key Beach and Siesta Key Village. For boating enthusiasts, you’ll find a beautiful marina with boat slips, as available, through the association. This property offers excellent income potential. Two-week minimum rentals are permitted, and owners may utilize the on-site property management office or manage rentals independently. Residents of Harbor Towers enjoy an exceptional collection of amenities, including: *A large marina *Gulf access (no fixed bridges) *Heated swimming pool and shallow wading pool *Three tennis courts *Fully equipped fitness center with new showers and saunas *Clubhouse with social spaces and large kitchen •Outdoor BBQ and kitchen prep area under a beautiful new awning *For boating enthusiasts, boat slips are available through the association plus an ample kayak storage area. Whether you're seeking a luxurious full-time residence, seasonal retreat, or income-generating property, Harbor Towers offers the perfect blend of resort living and coastal charm. Located near shops and restaurants and across the street from the world-famous Siesta Key Beach, don’t miss this rare opportunity to own your piece of paradise on Siesta Key.

5855 Midnight Pass Road Unit 333, Sarasota

$12,900,000

5 Beds ⋅ 7 Baths ⋅ Phillippi Shores SubDv. ⋅ 34242 Zip Code

Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house, and a separate waterfront cabana with bath. In total, the compound offers six bedrooms and six bathrooms, with gourmet kitchens in both the main house and guest house — each outfitted with high-end appliances throughout — ideal for multigenerational living, guest accommodations, or an exceptional private retreat. Throughout both residences, the finish detail is exceptional. Designer-selected materials create a cohesive and elevated aesthetic carried seamlessly across the entire compound. Custom wood flooring with intricate stone inlays, handcrafted stairwells featuring wood and stone risers, extensive crown molding, and refined architectural millwork highlight the level of craftsmanship invested in every space. Specialty stonework and thoughtfully curated finishes blend warmth with sophistication, creating interiors that feel timeless, substantial, and unmistakably high-end. Outdoor living is nothing short of spectacular. A dramatic infinity-edge pool with swim-assist system overlooks the water, enhanced by a striking waterfall feature that spills elegantly into the pool. New pool equipment (2025) supports the system. Natural rock waterfront frontage and a sculptural rock formation lead down to the shoreline, creating a one-of-a-kind coastal backdrop. Two docks serve the property — one with a double lift — offering outstanding boating access and rare protection on both sides of the point, with additional lift capacity for multiple watercraft. An outdoor shower provides added convenience after boating or swimming. Perched at the edge of the peninsula, the waterfront cabana and adjacent hot tub create a private, spa-like retreat suspended over the water — an unforgettable setting to take in sweeping sunset views. The residences were renovated separately: main house (2009) and guest house (2012). All A/C units have been renewed recently, along with the electric unit, and a new transformer (2024) services both properties. Sonos surround sound extends throughout all structures. Located on the highly desirable north end of Siesta Key, the estate offers convenient on-and-off island access while remaining just minutes from Southside Village and downtown Sarasota.

3750 Bayou Louise Lane, Sarasota

$1,400,000

2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

You will melt away on Crescent Beach's powder/sugary white sand and float away in the shimmering waters of the Gulf of Mexico. This residence has been beautifully renovated to provide the ultimate beach home for you to call your own. The kitchen area features a day bed and a custom wood top island. Enjoy your morning coffee or sunset drink on your private lanai. Residents enjoy the heated pool/spa with cabana and outdoor kitchen, two grilling areas, a sunset beachside deck and lighted pickle ball/tennis courts. You will appreciate the on-site management office, fitness room and large community center. Come see for yourself what Casarina offers for fine beachside living.

5880 Midnight Pass Road Unit 704, Sarasota

$2,750,000

2 Beds ⋅ 3 Baths ⋅ Midnight Harbor Sub SubDv. ⋅ 34242 Zip Code

A compelling canvas for architectural vision on the shores of Little Sarasota Bay. At the end of a quiet street in the established Siesta Key Midnight Harbor neighborhood, 1267 Starboard Lane offers a rare opportunity to design and construct a modern bayfront residence on one of the island’s distinctive waterfront sites. This .45-acre property features 287 feet of water frontage, with approximately 92 feet along the open bay and 195 feet along a protected canal, creating water exposure on two sides and expansive views across Little Sarasota Bay. The orientation allows a future residence to capture sweeping water vistas, coastal breezes, and memorable sunsets while also benefiting from the calm, protected canal frontage for boating access. The existing structure is being offered for land value, presenting an ideal opportunity to design a new residence that reflects today’s elevated coastal architecture and modern building standards. With generous frontage and lot depth, the site offers excellent flexibility for thoughtful design, allowing a future home to integrate elevated living levels, expansive terraces, resort-style outdoor spaces, and seamless indoor-outdoor connections that embrace the surrounding waterfront environment. The bayside frontage is enhanced by a seawall (2014), while the canal side provides sailboat water with no fixed bridges, offering direct access to the Intracoastal Waterway and Gulf beyond. Mature coastal trees add scale and natural beauty to the property, creating an established setting rarely found on newly developed waterfront parcels. Just moments from the white quartz sands of Siesta Beach and with convenient access to mainland Sarasota via the Stickney Point Bridge, the location offers a balance of island privacy and proximity to Sarasota’s vibrant arts, dining and cultural amenities. For architects, builders, or buyers seeking to create a distinctive new waterfront residence, this property presents an exceptional opportunity to shape the next chapter of Siesta Key living.

1267 Starboard Lane, Sarasota

$75,000

3 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code

Fractional Ownership. Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an expansive, updated designer-furnished residence that radiates elegance and comfort. The floor plan includes a primary suite, a secondary suite, and a spacious guest bedroom-all thoughtfully appointed with over $150,000 in custom furnishings. The gourmet kitchen is fully equipped with top-tier appliances from Wolf, Sub-Zero, and Fisher & Paykel, complemented by imported linens and every fine detail you’d expect in a luxury coastal retreat. As an owner, you’ll enjoy the legendary hospitality and resort-style amenities of Hyatt Vacation Club, including a full-service recreation and concierge team, assistance with local activities, valet parking, and 24-hour security. Every element has been curated to deliver a seamless blend of private ownership and world-class resort living. Own your piece of paradise—and indulge in the Siesta Key lifestyle you’ve always imagined, at a fraction of the cost of full ownership.

915 Seaside Drive Unit 504, Weeks 6-7, Sarasota

$580,000

2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code

This newly listed condominium presents a distinguished opportunity to own a fully furnished residence directly across the street from the number one ranked beach in the world. Situated across the street from Siesta Key public beach, this property offers an exceptional blend of coastal elegance and investment potential. The two-bedroom, two-bathroom split floor plan provides both privacy and functionality, complemented by easy-to-maintain tile flooring throughout. The screened lanai serves as the true centerpiece, offering breathtaking westerly sunset views over the beach and the heated community pool below, maintained at a comfortable eighty-five degrees for year-round enjoyment. For those seeking rental income, this property is ideally positioned within an established monthly rental program. Its remarkable proximity to the beach, dining, and shopping in both the North and South Siesta Villages makes it a consistently sought-after destination for vacationers throughout the year. The surrounding environment is nothing short of extraordinary. A short stroll leads to the pavilion and the warm, crystal-clear waters of the Gulf of Mexico. Nearby Phillippi Estate Park offers additional green space, while Morton's Siesta Market provides convenient grocery access just minutes away. Community amenities further elevate the ownership experience, including a full kitchen in the community room for entertaining, saunas in the common areas, gas grills in the pool area, and one covered assigned parking space. This meticulously maintained complex reflects genuine pride of ownership at every turn. Whether envisioned as a personal beach retreat or a productive investment property, this residence warrants your immediate attention. Schedule a private showing today.

5600 Beach Way Drive Unit 210, Sarasota

$2,490,000

3 Beds ⋅ 4 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

You will be WOWED! by this Furnished 2400+ Sq Ft of Elegant BEACHSIDE LIVING with (3) Generously Sized Bedrooms & (3.5) Baths with STUNNING FINISHES THROUGHOUT!.....RARELY AVAILABLE Corner Unit in this Special Boutique Community---a Resort-Style PET FRIENDLY "low density" plush 7 acre residential complex with over 200 feet of Powdery Quartz sand frontage along with "Old Florida" Clubhouse; Courts; Beachside Pool & Cabanas and an Onsite Manager....Upon Entrance you will be Greeted with a Grand Hallway that leads to a BRIGHT & SPACIOUS Floor Plan, reminiscent of a Single Story Home...Each Bedroom is Privately Located, each with it's own Full Baths....ENTERTAINING is "Extra Special" with Expansive Living Areas and Ideally Centrally Located Wet Bar....WELL-APPOINTED INTERIORS, including: Porcelain Tile throughout; Quartz Countertops; Hurricane Impact Windows/Sliders; "Hotel Style" Primary Suite with Seating Enclave & Sumptuous Ensuite Bath; Abundant Storage & Closet Space; In-Unit Laundry and Importantly...ease of Indoor/Outdoor Living with Multiple Sliders leading to "Wrap-Around" Balcony/Lanai--Perfect for Morning Coffees or Indulging your Favorite Cocktails while Watching Majestic Sunsets over the Gulf....*****Deeded Beach Access, convenient for long strolls collecting Seashells or just "Toes in the Sand" relaxing at Top Rated Siesta Key Beach. Dining/Shopping and Nightlife of the main village are just minutes away...GARAGE PARKING...---Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest!

5880 Midnight Pass Road Unit 511, Sarasota

$399,900

1 Beds ⋅ 1 Baths ⋅ Bay Oaks SubDv. ⋅ 34242 Zip Code

BEAUTIFUL 1 BEDROOM 1 BATH UNIT IN BAY OAKS on SIESTA KEY ** TURNKEY FURNISHED ** 1 WEEK RENTALS ALLOWED ** The waves crash, the sand is sugar-coated and the sunsets are striking on Siesta Key.. There is no better location to invest in a 2nd home or investment property. This condo is located on the 2nd floor of building E in Bay Oaks. You will love the large open kitchen and expansive design of this "Santa Fe" themed unit. Located at the end of the 2nd floor in a corner of the building, privacy and tree lined views from the patio create serenity for the owner and tenants. Boasting 750ft2 of living area, there is no wasted space with eat-in dining and wide-open family space. The master bedroom is also open & airy with an on-suite vanity and large walk-in closet, including a washer/dryer. Bay oaks is located just north of the Stickney point bridge allowing more quick escape off the island to Publix, Bealls, Starbucks and Gulf Gate shopping. The community provides a wonderful community pool and tennis court with a full-time manager on site. Beach access 12 is the best public access to the white sands of Siesta Key or catch the Trolley and enjoy and scenic ride to the public beach. Now is the time to invest in Siesta Key real estate.

6157 Midnight Pass Road Unit E22, Sarasota

$1,495,000

2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code

This Rare Beachfront, Classic Coastal Modern extensively renovated 2/2 condo has your Dream View! Unobstructed Beach View of 400’ of private beach on 7 acres. Offering total building area for unit is 1568 sq ft. Modern appointed living area is 1316sq ft with additional 252 sq ft Modern Private Lanai. High demand all year Monthly (12) rentals for Investor, 2nd Home or Primary Home. Passed Structural Integrity. Strong, Fully Funded Reserves. Replaced cast iron to New “PVC” drains in entire building, New building roof, New clubhouse roof lowered insurance master policy. Stilted Building, Designated Parking underneath. Gated with 24 Hr Security. Condo has Brand New HVAC 2026 with R454B gov. required cooling & New Water Tank. Designed by Owner, Floor to Ceiling integrating a cohesive Classic Coastal Modern feel throughout. Enjoy your “private outdoor living” new screened 31’x8’ Beach Lanai (no houses/buildings in line of sight) Modern flooring, locking storage Door. Condo is insulated & extremely “Quiet” w/updated PGT impact Sliders and Windows. Solar Shades are see-through when down on sliders but front windows have see-through Solar Shades & Privacy Shades. The Front has Quiet Solid Core Impact Door. Wi-Fi Thermostat. Stunning Modern Polished Porcelain, Large Rectified 24” Tile for entire condo & closets. Modern Frosted Glass Framed Solid Wood 4 Interior Doors. Frosted Glass Framed Solid Wood Interior Bifolds for all 7 closets, continuing a clean line design with 8” Solid Wood, Mitered Baseboards throughout. Calming Lighting with all LED lighting dimmers throughout & all walk-in closets. All Closets designed w/Solid Wood Shelving & fitted w/thick satin nickel Rods and Brackets to All Studs for Heavy organization needs. Both Bathrooms have Moreno Gloss Floating Soft Close Drawer Vanities w/satin nickel Series Pfister Kenzo Waterfall Faucets/Shower Handel & 4 piece Towel bar set. Kohler Skirted “Chair-Height” Toilets for both. Main bath is Designed w/24” Italian Carrera Marble Tile, full size Bench & tall Niche. Guest bathroom Designed w/24” Ivory Glass Tile & Tall Abalone Tile Niche. With owners not being a chef/cook, kitchen is gently used in immaculate condition. ALL "SMART Wi-Fi" Stainless Appliance Suite, Largest Size features; “Double Oven” 5 burner w/Warming Drawer. Refrigerator “Showcase” Triple French Door, ice/water, Middle Flex Drawer, Bottom Freezer Double Drawer. Stainless “Triple Storm” Dishwasher. Kohler 36” Large Stainless Steel Apron Sink w/Kohler Pull down Stainless Faucet. Matching to Suite are Over Size Stainless "Wi-Fi" Front Load Washing Machine & Front Load Dryer on Stainless Pedestals in “walk-in” Laundry Room, stainless light, solid wood shelving w/nickel stainless rod/brackets designed for Heavy storage needs. Owner has variety remodeled Product in front closet. This beachfront condo has been gently lived in and all the Design Aspects/Appliances are in Immaculate Condition. Clubhouse w/ 25‘x40‘ Heated Swimming Pool, Tennis & Pickleball Courts, updated Fitness room, bathrooms, your private locked Storage Room. Private Beach gate to Boardwalk w/ picnic area, 2 grills & birdwatching benches. Pet friendly, designated large pet park w/bench. “Private ISLAND Style Living” A truly Coveted Opportunity awaits you- private, unobstructed view, full condo length beachfront lanai, 6 floor, 7 acre property & 400’ beachfront. Property is available for Same Day Showings.

420 Beach Road Unit 606, Sarasota

$1,475,000

4 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.

3360 Higel Avenue, Sarasota

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

Imagine awakening each morning to the gentle symphony of waves caressing powder-white sand on Siesta Key, where the Gulf of Mexico stretches endlessly before you in shimmering turquoise splendor. This exquisite two-bedroom, two-bathroom condominium nestled within the prestigious Casarina community offers a lifestyle that transcends ordinary coastal living. Perched elegantly upon seven acres of lush, tropical grounds directly on world-renowned Crescent Beach, this beautifully updated residence delivers the quintessential beach sanctuary you have been dreaming of. Hurricane impact windows provide peace of mind while framing breathtaking beach and gulf views that will steal your breath daily. The thoughtfully renovated kitchen boasts stainless steel appliances, while sophisticated stone-look tile graces the lanai, creating a seamless indoor-outdoor retreat. Beyond your private haven, Casarina's resort-caliber amenities rival the finest destinations. An expansive heated pool and spa with cabana and outdoor kitchen beckons lazy afternoons, while two grilling areas invite convivial gatherings under swaying palms. A sunset beach-side deck transforms evenings into pure magic, and lighted tennis and pickle-ball courts satisfy your competitive spirit. The community thoughtfully provides an on-site management office, fitness room, and generous community center for celebrations and social events. Just moments away, the charming Siesta Key Village offers eclectic dining and boutique shopping, while Phillippi Estate Park provides serene natural escapes. Whether you envision this as your permanent paradise or a cherished seasonal retreat, this freshly repainted gem delivers beach-side living at its absolute finest. Schedule your private showing today and let the Gulf whisper your name.

5880 Midnight Pass Road Unit 605, Sarasota

$546,662

2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code

BEACH VIEWS, RENTAL FLEXIBILITY, AND THE ULTIMATE SIESTA KEY LIFESTYLE! Welcome to La Siesta Condominiums, where the sugar-white sands of Siesta Key Beach are quite literally across the street and every day feels like a vacation. Perched on the third floor, this beautifully furnished and move-in ready 2-bedroom, 1-bath condo enjoys sweeping views of the Gulf, beach, and resort-style community amenities below. Whether you’re searching for a personal coastal retreat, an income-producing investment property, or the perfect combination of both, this residence offers an exceptional opportunity in one of Siesta Key’s most desirable communities. Inside, you’ll find 753 square feet of thoughtfully designed living space featuring an open-concept layout, abundant natural light, and a screened lanai where you can relax with your morning coffee while enjoying the tropical breeze and picturesque views. The spacious primary bedroom offers a king-size bed, while the guest bedroom is configured with two twin beds, providing comfortable accommodations for family and guests alike. The condo is being offered furnished and is ready for immediate enjoyment. Additional features include hurricane impact windows and doors, a newer roof, updated HVAC system, covered parking, elevator access, guest parking, and a private ground-floor storage closet perfect for all your beach gear. La Siesta is beloved for its resort-style amenities, including a heated pool, clubhouse, fitness center, shuffleboard courts, BBQ area, on-site management, and a dedicated rental office. Owners enjoy a truly hands-off ownership experience with professional management available for guest reservations, check-ins, and check-outs. One of the property’s most attractive features is its exceptional rental flexibility. Participate in the on-site rental program, self-manage, utilize Airbnb, or enjoy the condo exclusively for personal use. With weekly rentals permitted, renters required to be 25 years of age or older, and Siesta Key’s year-round popularity, the income potential is substantial. Located just moments from Siesta Key Village’s restaurants, shopping, nightlife, and entertainment, you’ll enjoy the perfect balance of relaxation and convenience. Properties offering beach views, rental flexibility, resort amenities, and one of the best beach locations on Florida’s Gulf Coast are increasingly hard to find. Don’t miss your opportunity to own a piece of paradise at La Siesta. Schedule your private showing today.

915 Beach Road Unit 318, Siesta Key

Homes With Pool For Sale In Siesta Key FL

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