Location: Sarasota, 34242
Do Not Show Listings
1308 OLD STICKNEY POINT RD #WP3, SARASOTA, FL 34242
$15,000159 Days on yellowkey MLS ID: A4681452
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3524 Built: 2002Community: Marina Del SolCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: Riverview High
Tax Year:
Middle School: Brookside Middle
Remarks: AVAILABLE 1/4/27 Experience the pinnacle of coastal living in this exceptional penthouse at Marina Del Sol with PRIVATE 52 FT BOAT SLIP. Perfectly positioned moments from the #1-rated Siesta Key Beach. This rare residence offers panoramic Gulf of Mexico sunsets on one side and serene Bay views on the other—an unmatched indoor-outdoor lifestyle framed by water in every direction.****Designed for privacy and comfort, the penthouse features three expansive suites, each with its own en-suite bathroom, ideal for hosting guests or multi-generational stays. Four private balconies extend the living space outdoors, perfect for morning coffee, afternoon breezes, and sunset cocktails.****For boating enthusiasts, a private 52-foot boat slip is available, providing direct access to Sarasota Bay and the Intracoastal—an extraordinary amenity rarely paired with a luxury penthouse.****Additional highlights include:**Open, light-filled living areas with sweeping water views**Elevator access directly to front door and secure, resort-style community**Walk/bike to dining, shops, and beach access**Prime location near Stickney Point Bridge for easy on/off-island access**Whether you’re seeking a seasonal escape or an extended coastal retreat, this Marina Del Sol penthouse delivers space, views, and boating convenience—all in one of Siesta Key’s most coveted waterfront settings.*** Inquire for availability, rates, and boat slip details. Available for Annual, Seasonal or Monthly Rental.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
SARASOTA, FL 34242
$7,85055 Days on yellowkey MLS ID: O6409341
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976Community: Harbor Towers Y & RCondo
High School: None
Middle School: None
Remarks: FULLY FURNISHED AND INTERIOR DESIGNED 2 BEDROOM / 2 BATH UNIT now available in Harbor Towers on Siesta Key. This beautifully designed condo offers a total of 1,700 sq ft of indoor/outdoor living, including 1,152 sq ft of air-conditioned space and a spacious 540 sq ft private patio finished with travertine and turf. The unit features 9 ft ceilings, floor-to-ceiling windows, stylish furnishings, and a thoughtfully designed layout that creates a bright, comfortable, and inviting living space. The private patio is beautifully furnished and overlooks the marina, offering the perfect setting to relax and enjoy the Siesta Key lifestyle. Harbor Towers offers some of the most desirable amenities on Siesta Key, including a fully equipped Precor gym, heated pool, club room, marina, kayak launch, BBQ area, waterfront pavilion, and 3 lighted Har-Tru tennis courts. Schedule your appointment today to experience this exceptional opportunity and enjoy the best of Siesta Key living!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Andres Ospina Rivera (321-821-8446)
1257 S PORTOFINO DR #38ALBA, SARASOTA, FL 34242
$4,5001275 Days on yellowkey MLS ID: T3423422
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968Community: Siesta Harbor ICondo
Remarks: Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the lanai overlooking the boat slips and the Intracoastal waterway. Amenities include deeded beach access to the #1 rated beach - a 5 minute walk across the street, heated community pool and spa, sauna, shuffleboard, community room with library and pool table, BBQ grills and picnic area. A gym and fishing pier are also on site. Enjoy water aerobics classes Monday-Friday as well as other organized gatherings and happy hours at the club house. Convenient to shops, restaurants, delicatessens and grocery stores. Laundry not in unit, however it's conveniently located at no expense. No car needed as everything is close by. A free trolley runs up and down the island taking you to all that Siesta Key has to offer including Siesta Key Village shops and restaurants, numerous outdoor bars and restaurants and Public beaches. Close proximity to Stickney Point Bridge enables easy access on and off the Key. High season rate of $6500 January through April (Leased Dec. 1st 2025-May 30th 2026) Application Fee $150; $500 security deposit and 14% taxes due from guest. Exit cleaning fee $175 deducted from security deposit. One occupant must be 55 or over to rent this unit. Sorry, no pets allowed. 1 car allowed on the property.
Listing is courtesy of: SIGNATURE REALTY ASSOCIATES (813-689-3115)
Listing Agent: Katherine Esposito (813-695-3989)
8776 MIDNIGHT PASS RD #C107, SARASOTA, FL 34242
$3,500337 Days on yellowkey MLS ID: A4661654
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1338 Built: 1975Community: Island Reef ISpa: NoCondo
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Remarks: Available 8/10-12/25/26. Not Available January 1-through April 5th... 2027. Experience the best of Siesta Key living at the Island Reef Association on Turtle Beach. This beautifully designed condo is offered fully turnkey furnished, showcasing exceptional attention to detail and high-quality finishes throughout. Island Reef delivers Beach-to-Bay luxury resort-style living with amenities that include two heated pools, a fitness center, covered parking, and private beach access. Just across the street, enjoy pickleball or tennis on the newly resurfaced courts, or head to the Island Reef boat docks for kayak launching or to tie up your own boat—or a rental—during your stay. Inside, you’ll find generously sized primary and guest suites in this 2-bedroom, 2-bathroom condo, enhanced with plantation-style shutters, tropical-inspired décor, and tasteful art glass lighting fixtures. The kitchen boasts granite countertops and a high-end appliance package, making cooking a pleasure. A convenient in-unit laundry adds to the ease of living. All of this is just steps from the private Turtle Beach access, where you can enjoy biking, boating, beach days, swimming, tennis, pickleball, and vibrant community social events. Yes… you can have it all!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
681 AVENIDA DE MAYO, SARASOTA, FL 34242
$11,00061 Days on yellowkey MLS ID: A4693410
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3324 Built: 1947Community: Sarasota BeachSpa: NoSingle Family
Remarks: Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply unwinding after a day at the beach and boating. These multi-purpose rooms adapt to your lifestyle, whether you need another bedroom, home office, fitness space, or creative art studio. A true showstopper awaits outside, where a Lucas Lagoons designed pool transforms your outdoor living area into a resort-worthy oasis. Known for creating breathtaking aquatic masterpieces, this signature pool feature turns everyday swimming into a resort setting for entertainment. Imagine hosting poolside gatherings that friends will talk about for years to come! Sun worshippers will appreciate the large rooftop tanning area—your private perch for soaking up Florida's famous sunshine while enjoying gentle Gulf breezes. It's like having your own exclusive sundeck without the crowds. This house is the perfect balance between contemporary sophistication and vacation-like comfort. Beautiful, neutral finishes throughout create an atmosphere of elegance without sacrificing that relaxed coastal vibe that makes Siesta Key special. Location? Simply unbeatable. Situated in central Siesta Key, you're just a stroll from the bustling Siesta Key Marketplace where local shops and dining options abound. Siesta Market is less than a 10-minute walk away—perfect for picking up ingredients for an impromptu dinner or beach picnic. For those who appreciate the island's famous nightlife, Siesta Key Oyster Bar and Daiquiri Deck are within easy walking distance. Meanwhile, the world-renowned Siesta Beach—celebrated for its powder-fine white sand—is just a short bike ride from your doorstep. The primary bedroom offers a serene retreat after days filled with sunshine and adventure, while the additional bedrooms provide comfortable accommodations for family and guests. This isn't just a house—it's an invitation to embrace the laid-back yet luxurious Siesta Key lifestyle. Where morning coffee comes with water views, weekends blend into beach days, and every evening feels like a vacation. Why visit paradise when you can live there?
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Colette Jay (941-713-7711)
131 WHISPERING SANDS CIR #V33, SARASOTA, FL 34242
$3,950112 Days on yellowkey MLS ID: A4687180
REDUCED by $800 (16.8%) on 05/11/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1264 Built: 1968Community: Whispering Sands Sec 5Villa
Remarks: Live the Siesta Key lifestyle in this beautifully updated 2-bedroom, 2-bath residence offering approximately 1,600 sq ft of usable living space, tucked inside one of the island’s most desirable 55+ Gulf-front communities, just a short stroll to Siesta Key Village. The additional square footage comes from a fully finished garage complete with A/C and a built-in Murphy bed, creating the perfect flex space for guests, a home office, or additional living. Inside, the home feels light, bright, and effortlessly coastal with wood-look porcelain tile flooring throughout and a clean, neutral palette that complements any style. The kitchen has been thoughtfully updated with cream cabinetry, granite countertops, a modern backsplash, and island space, along with a full appliance package designed for both everyday ease and entertaining. Both bathrooms feature sleek, walk-in glass showers and updated finishes, while the layout offers spacious bedrooms, generous closet space, and abundant natural light throughout. A private outdoor space creates the perfect setting for morning coffee, evening wine, or simply enjoying the Gulf breeze. What truly sets this residence apart is the lifestyle. Residents enjoy 800 feet of private quartz sand beach on the Gulf, a beachside pool, an additional pool with subtle water views, fitness center, clubhouse, shuffleboard courts, and kayak/canoe storage, along with on-site management, maintenance, and security for peace of mind. Located just steps from Siesta Key Village’s top-rated dining, boutique shopping, and vibrant nightlife, everything you need is right outside your door. This is the kind of rental that rarely becomes available and never lasts. Live where others vacation.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
5151 OAKMONT PL, SARASOTA, FL 34242
$2,95068 Days on yellowkey MLS ID: A4692892
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1953 Built: 1977Community: Siesta BeachSingle Family
Remarks: Welcome to your dream home at 5151 Oakmont Place, nestled in the heart of the stunning Siesta Key, Sarasota, FL. This charming 3-bedroom, 2-bathroom residence offers 1,953 square feet of modern living space, designed for both comfort and style. Step inside to discover a thoughtfully laid-out floor plan that seamlessly blends contemporary design with functionality. The kitchen is a chef's delight, featuring sleek granite countertops and stainless steel appliances, perfect for culinary adventures. The bathrooms boast contemporary vanities and matching granite countertops, adding a touch of elegance to your daily routine. Enjoy the Florida sunshine in your private outdoor space, ideal for relaxing or entertaining guests. The home is equipped with central heating and air conditioning, ensuring year-round comfort. The attached two-car garage not only provides ample storage but also includes a convenient workspace for your projects. This pet-friendly home, with conditions, is unfurnished, allowing you to personalize it to your taste. Located approximately 1.5 miles from one of the best beaches in the country, you'll have easy access to the vibrant Siesta Key Village and a short drive to downtown Sarasota. Whether you're looking for a serene retreat or a lively community, this centrally located gem offers the best of both worlds. Don't miss the opportunity to make this beautiful home yours! Tenant will be responsible for a monthly lawn fee of $200.00.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Beth Harris (941-321-7148)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$5,50087 Days on yellowkey MLS ID: A4690579
REDUCED by $1,000 (15.4%) on 05/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1331 Built: 1975Spa: YesCondo
Remarks: Also for SALE! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Schedule your private showing today.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
9393 MIDNIGHT PASS RD #605, SARASOTA, FL 34242
$2,495853 Days on yellowkey MLS ID: A4603196
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1975Community: Pointe On Midnight PassCondo
Remarks: Beautifully decorated 2 bedroom 2 bath condo located at The Pointe on Midnight Pass Road. Large lanai accessible from master bedroom and living room features views of the Intracoastal. Look out your kitchen window and guest bedroom for a view of the beautiful Gulf. Beautiful furnishings, full size washer/dryer. Complex amenities include heated pool, whirlpool, sauna, fitness room, tennis court & party rooms. Pets are not permitted.
Listing is courtesy of: CASEY REALTY CORPORATION (941-922-3391)
Listing Agent: Pamala Casey (941-922-3391)
9200 MIDNIGHT PASS RD #24, SARASOTA, FL 34242
$2,35089 Days on yellowkey MLS ID: A4690246
REDUCED by $100 (4.1%) on 05/06/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 706 Built: 1972Community: Inlet AptsCondo
Remarks: Available May through October 15th 2026... Not Open for Winter Season 2027... Welcome to your slice of paradise in Siesta Key! This beautifully updated condo at 9200 Midnight Pass Rd, Apt 24 offers stunning water views and the perfect blend of comfort and coastal charm. This inviting unit features a spacious king-sized bedroom and full bathroom, along with custom-built bunk beds—ideal for guests or added sleeping flexibility. The fully enclosed Florida Room with windows expands the living space, creating a bright and airy environment perfect for relaxing or entertaining. Enjoy breathtaking Gulf sunset views right from your private lanai, the perfect spot to unwind after a day at the beach. The recently renovated kitchen is equipped with stainless steel appliances and sleek granite countertops, while wood and tile flooring throughout provide both style and easy maintenance. Residents will appreciate access to excellent community amenities, including boat dockage, Gulf and canal views, a heated swimming pool, and on-site laundry facilities. Ideally located just moments from the world-renowned beaches and a short ride to Siesta Key Village, where you can enjoy shopping, dining, and entertainment. Whether you're walking along the soft sandy shores, kayaking through peaceful canals, or exploring the island, this location offers the ultimate beach lifestyle. Unit #24 is the perfect place to call home—don’t miss this opportunity to live in paradise! Taxes and fees will apply to base rent.
3939 HIGEL AVE, SARASOTA, FL 34242
$22,00070 Days on yellowkey MLS ID: A4692589
Bed: 3 Bath: 3.5 Gar: 8 Liv Area Sq Ft: 3788 Built: 2022Community: Siesta Rev OfSpa: YesSingle Family
Remarks: Arrive. Unwind. Experience Siesta Key at its finest. Welcome to your private luxury retreat on Siesta Key, a modern sophisticated 4-bedroom, 4-bathroom home designed for elevated coastal living. Tucked away in one of the island’s most desirable locations, this residence offers the perfect blend of privacy, comfort, and effortless elegance. From the moment you step inside, you’re welcomed by light-filled interiors, thoughtfully designed spaces, and a calming, refined aesthetic, and tropical views. Each bedroom serves as a peaceful sanctuary, while four well-appointed bathrooms provide both convenience and privacy, ideal for families, couples, or executive getaways. The home is designed for seamless living with an open concept. Spacious gathering areas invite connection including a built-in deck spa, while modern amenities including climate-controlled comfort, quality linens, and everyday essentials to ensure a stay that feels both luxurious and easy. Whether you’re getting ready for an evening out or returning from a sun-soaked beach day, every detail has been considered. Spend your days exploring the powdery white sands of nearby Siesta Beach and Village, consistently ranked among the best beaches in the world, or enjoy the vibrant dining and shopping scene just minutes away in Siesta Key Village. Also, for entertainment purposes, the property is close to Sarasota and the downtown main street area. As the day winds down, return to your private retreat to relax, recharge, and savor the quiet luxury of island living. This is more than a place to stay, it’s a curated Siesta Key experience.
Listing is courtesy of: GOOD LIFE REALTY LLC (941-342-9889)
Listing Agent: Raffilena Hamilton (941-685-2441)
8911 MIDNIGHT PASS RD #514, SARASOTA, FL 34242
$3,550984 Days on yellowkey MLS ID: A4588110
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1233 Built: 1973Community: Sunrise Cove Sec 2Condo
Remarks: BOOKED FEB/APRIL 2026. AVAILABLE JANUARY 2026. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon entering the condo, you will immediately fall in love with the bright open plan dining and extended living room, all tastefully furnished and decorated. The fully equipped kitchen has quartz counters, custom cabinets and new stainless-steel appliances. The Master Bedroom has plantation shutters and more amazing views of the bay, the Master Bathroom was also expanded to provide more space and has a walk-in shower and single vanity. Luxury Vinyl in both the bedrooms and tiled throughout the living areas. Guest bedroom with queen size bed and walk-in closet, and the guest bathroom also has a walk-in shower and single vanity. From the front balcony you will have views of the Gulf, common laundry areas are on each floor, private storage lockers and a trash chute. Plus, 1 assigned parking carport in front of the building and additional guest parking. Sunrise Cove offers many social activities and amenities, which includes a large clubhouse with kitchen, billiards 2 tennis & 4 pickleball courts, fitness rooms, game room, club house, kayak racks, fishing docks, bayside picnic area with gas grills, 2 heated pools overlooking the Bay, and the Jr. Olympic pool is on a peninsula which juts out onto the Bay. Walk across the street the Turtle Beach Access, and you are right next door to Turtles Restaurant, and only .2 miles from the fabulous Ophelia's Bayfront Restaurant. There is a Free Trolley stop directly across the street from the complex, with free rides to the famous #1 Siesta Key Beach with its crystal quartz sand, Siesta Key Village where you will find shopping and restaurants. If you enjoy the nightlife, Siesta key village is where it's at! This is the absolute perfect island getaway. Don't let this one slip away!!
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Chrissie Cummings (772-532-8229)
9200 MIDNIGHT PASS RD #10, SARASOTA, FL 34242
$2,000496 Days on yellowkey MLS ID: A4643306
REDUCED by $500 (20.0%) on 05/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 895 Built: 1972Community: Inlet AptsSpa: NoCondo
Remarks: Waterfront Paradise on Siesta Key – Turnkey Furnished 2BR/2BA Condo! Experience the ultimate in coastal living with this completely remodeled, turnkey furnished 2-bedroom, 2-bathroom waterfront condo on the south end of Siesta Key, just past Turtle Beach! This ground-floor unit offers stunning water views from the lanai, a beautifully updated kitchen and bathrooms, and brand-new furnishings—including a king-size mattress in the master bedroom and a queen-size bed in the guestroom. Enjoy resort-style amenities, including a heated pool, and the convenience of reserved parking right outside your door. Whether you’re looking for a vacation from the cold, a place for a month to look around to buy or while your place is getting remodeled this condo is the perfect retreat! Available May 1-Sept 15, 2026 Don’t miss this rare opportunity—schedule a showing today!
1145 HORIZON VIEW DR, SARASOTA, FL 34242
$15,000231 Days on yellowkey MLS ID: A4673276
Bed: 4 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 4306 Built: 1980Community: Tortoise EstatesSpa: YesSingle Family
Remarks: Available : 2026: Open September 1 through November 15th 2027 - 30 Day Minimum Stay... 2027: Peak Season Now Open for January and April. February and March are not available.. Experience the best of Siesta Key living with private beach access—this expansive, exceptional home offers everything needed for the perfect coastal escape. Thoughtfully designed indoor and outdoor living spaces create comfort and privacy even when hosting a full house. Each bedroom, along with the main living area, opens to its own deck, providing the perfect spot to savor morning coffee, unwind with a book, or soak up the sunshine. A custom heated pool and spa add to the home’s private resort feel, while tasteful updates throughout make it a serene coastal get-away. Nestled on a quiet dead-end street—one so tucked away that even many locals don’t know it exists—this rare gem defines beachfront living at its finest. It’s a unique opportunity to claim your own slice of paradise. Just steps from the powder-soft sands of Siesta Key, with deeded beach access leading directly to Turtle Beach, this home places the island’s most coveted amenity right at your doorstep. Whether you're heading out for peaceful morning walks, unforgettable sunsets, or the convenience of a close-by spot for all your beach gear, this residence offers the ideal home base for your dream coastal getaway. Taxes and fees apply to base rent..
5400 OCEAN BLVD #5-3, SARASOTA, FL 34242
$6,00071 Days on yellowkey MLS ID: A4692374
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 928 Built: 1970Community: TerraceCondo
Middle School: McIntosh Middle
Remarks: SEASONAL OR ANNUAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it’s best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280 sq ft of indoor-outdoor space with sweeping Gulf views and stunning sunsets. The open-concept living area includes a chef’s kitchen with Quartzite countertops, custom European cabinetry, premium stainless appliances, and a large island, plus a custom Murphy bed for guests. The serene primary suite offers a spa-like bath with glass walk-in shower and elegant finishes, while recent upgrades like a new A/C system ensure year-round comfort. Residents enjoy a heated saltwater Gulf-view pool, fitness center, community lounge, and controlled-access security, all just steps from the beach and a short walk to Siesta Key Village’s shops, cafés, and dining—with downtown Sarasota’s arts and culture only minutes away. Perfect for seasonal or annual stays. High season rates are $14000/month. Off season rates are $9000/month. The annual rate is $6000/month.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Alex Lane (941-960-3080)
8776 MIDNIGHT PASS RD #C307, SARASOTA, FL 34242
$2,950341 Days on yellowkey MLS ID: A4661169
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1338 Built: 1975Community: Island Reef ICondo
Remarks: Available June 1 2026 at this time. Experience the best of Beach to Bay Luxury Resort-Style Living in this beautifully designed 2-bedroom, 2-bathroom condo located in the sought-after Island Reef Association on Turtle Beach, Siesta Key. This spacious unit has been professionally designed and is offered fully turnkey furnished, with exceptional attention to detail and high-end finishes throughout. Step inside to find a bright and inviting interior featuring plantation shutters, tropical-inspired colors, tasteful art glass lighting, and granite countertops paired with a premium appliance package—making everyday living and entertaining a breeze. The generous primary and guest suites provide ample comfort, while in-unit laundry adds everyday convenience. Island Reef offers an unbeatable lifestyle with private beach access, two heated pools, a fitness center, clubhouse, covered parking, and so much more. Just a short stroll away, enjoy the newly resurfaced tennis and pickleball courts, or head to the Island Reef boat docks—perfect for launching kayaks or docking your boat or rental during your stay. Located just steps from the private access to Turtle Beach, you’re perfectly positioned to enjoy everything Siesta Key has to offer—boating, beachcombing, swimming, biking, tennis, pickleball, and a vibrant social scene. Yes... you really can have it all!
431 ISLAND CIR, SARASOTA, FL 34242
$8,00074 Days on yellowkey MLS ID: A4691247
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2346 Built: 1962Community: Sarasota BeachSpa: NoSingle Family
Remarks: This is a short term rental. Listing reflects off season rate. New to the rental market! Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Island Retreat offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and Siesta Key Village make it an exceptional choice for creating unforgettable memories. Featuring 5 beautifully appointed bedrooms, this home comfortably sleeps up to 10 guests. Each room is thoughtfully designed with plush bedding, contemporary furnishings, and ample natural light, ensuring a restful and rejuvenating stay. Every detail of this home has been meticulously updated to provide a seamless blend of luxury and comfort. Enjoy an open-concept living area with sleek hardwood floors, a gourmet kitchen featuring stainless steel appliances, quartz countertops and an oversized breakfast bar offering plenty of seating. Dive into relaxation with your own private heated pool, perfect for a refreshing swim or lounging poolside under the warm Florida sun. The pool area is surrounded by lush tropical landscaping, offering privacy and a tranquil oasis for unwinding and a convenient outdoor shower to rinse off after a day at Siesta Key Beach which is just a few blocks away.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
7372 MELALEUCA WAY, SARASOTA, FL 34242
$8,00088 Days on yellowkey MLS ID: A4690292
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2600 Built: 1967Community: Siesta Properties IncSingle Family
Remarks: Offered furnished, this beautifully remodeled 4-bedroom, 2-bath residence in the gated Sanderling Club presents a rare lease opportunity on the south end of Siesta Key. Set on three quarters acre behind a private gate near the entrance to the community, the approximately 2,600-square-foot home offers a spacious and flexible layout with updated finishes throughout, expansive living and dining areas, a stunning renovated kitchen, and a thoughtfully designed owner's suite with doors that close off the adjoining office, hallway, primary bedroom, and luxury bath for added privacy and versatility. The outdoor setting is equally impressive, with an expansive tropical backyard designed for both enjoyment and ease of care, featuring low-maintenance landscaping, two paved deck areas, and a fire pit that creates a peaceful backdrop for relaxing or entertaining. A detached 2-car garage and abundant onsite parking add to the property's functionality. Located within Sanderling Club, an exclusive waterfront community known for its privacy, natural beauty, and coastal character, residents enjoy access to a private Gulf-front beach, tennis, pickleball, a playground, and a clubhouse currently being renovated. The location places you near Siesta Key's South Village with local dining and conveniences, while also offering easy access to Siesta Beach and Turtle Beach. Lease terms are subject to community rules and approval as a Limited Member for the duration of the lease or one year, whichever is shorter. Minimum lease is 6 months, no more than two leases in a 12-month period, no subletting allowed, and fees include a $150 per applicant background and credit check plus a $500 Limited Membership fee.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Shane Lewis (941-685-3252)
307 AVENIDA DE PARADISIO, SARASOTA, FL 34242
$12,00077 Days on yellowkey MLS ID: A4691362
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1511 Built: 1972Community: Paradise IslandSingle Family
Remarks: Welcome to your dream escape on Siesta Key—a completely reimagined coastal retreat designed to make every moment unforgettable. Tucked away on a quiet stretch of Avenida de Parasido, this stunning 3-bedroom, 2-bath home has been fully remodeled from top to bottom with brand-new, designer furnishings. Everything is fresh, pristine, and waiting, be among the very first to experience it. Step inside to an airy, light-filled space where coastal elegance meets effortless comfort. The open layout invites connection—whether you’re sharing meals, relaxing after the beach, or simply enjoying the calm of your surroundings. Out back, your private oasis awaits. A secluded yard wraps around a sparkling pool, creating the perfect setting for morning coffee, sun-soaked afternoons, or quiet evenings under the stars. It’s your own slice of paradise—peaceful, private, and entirely yours. Location is everything—and this one is unbeatable. You’re just steps from the heart of Siesta Key Village, where vibrant local life unfolds. Discover eclectic restaurants loved by locals, charming boutiques unique to Sarasota, live music drifting through warm evenings, and an energy that’s both relaxed and alive. And then there’s the beach. Just moments away lies the world-famous Siesta Key Beach—renowned for its powdery white quartz sand and the crystal-clear waters of the Gulf. Whether you’re swimming, sunbathing, or catching a sunset that feels almost unreal, this is coastal living at its finest. When you’re ready to explore beyond the island, downtown Sarasota is only minutes away. Immerse yourself in a thriving arts scene with live theater, ballet, multiple orchestras, and an impressive collection of galleries. Food lovers will appreciate the exceptional dining culture—this area boasts one of the highest concentrations of top-rated restaurants per capita in the country. This isn’t just a place to stay, it’s where beach days, vibrant nights, and total relaxation come together effortlessly. All that’s missing is you.
5760 MIDNIGHT PASS ROAD #208D, SARASOTA, FL 34242
$5,0001350 Days on yellowkey MLS ID: A4550517
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1981Community: Gulf & Bay ClubCondo
Remarks: Listing reflects off-season rate. Available August - December 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot to unwind. Step inside to discover a large kitchen, ideal for preparing meals and entertaining. The primary suite offers complete relaxation with a comfortable king-sized bed, a cozy spot to read a good book, and a large ensuite bathroom with a walk-in shower. Up to bringing friends or family? There's plenty of room in the guest bedroom, offering two double beds and their own access to the guest bathroom. Did we mention paradise includes your own wet bar and wine fridge!? Pour yourself a drink of your choice, walk over to watch the exquisite sunsets in the enclosed patio, and don't forget to open the sliding glass windows to let the cool ocean breeze in! Enjoy Gulf & Bay’s impressive amenities including 3 heated pools, 8 tennis courts, a fitness center, BBQ areas, and private access to Siesta Key Beach! You've waited so long, and now the wait is over, you've got 2 tickets to paradise!
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