Location: Sarasota , 34242
Do Not Show Listings
8770 MIDNIGHT PASS RD #302B, SARASOTA, FL 34242
$4,0001087 Days on yellowkey MLS ID: A4573996
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1975Community: Island Reef ICondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks (lifts allowed), two lit tennis courts, pickleball, 2 fitness rooms, kayak storage, library, billiards, game room, clubhouse, two heated swimming pools, on site manager and more. Pet friendly! Imagine rising each day to panoramic vistas of the Gulf of Mexico, and to view coastal wildlife and breathtaking sunsets. Stroll over to the Bayside to enjoy the refreshing breezes and magnificent sunrises. Tropical gardens add to the appeal of Island Reef. Your new social life awaits a perfect 3-5 minutes walk to a trio of Siesta’s Keys favorite restaurants (casual and waterfront fine dining) or enjoy a complimentary trolley to Siesta Village for dining, shopping, ice crèam, mini donuts, cute brunch spots, yoga, and dancing every night of the week! SEASONAL GULF SIDE PRICE SCHEDULE: Jan-March 2026-$7,700.00 Leased (Unavailable January-March & April 2026) May-December 2026 is available. May 1st through December 30th 2026 is still available at $4,000.00 monthly.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Erick Shumway (941-544-3718)
681 AVENIDA DE MAYO, SARASOTA, FL 34242
$11,00028 Days on yellowkey MLS ID: A4693410
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3324 Built: 1947Community: Sarasota BeachSpa: NoSingle Family
High School: Sarasota High
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)
1355 S PORTOFINO DR #103, SARASOTA, FL 34242
$12,00029 Days on yellowkey MLS ID: A4693257
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1389 Built: 1975Community: Siesta Harbor IiiCondo
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This rarely available rental includes a dedicated boat slip at no additional cost—perfect for bringing your boat or simply enjoying the waterfront lifestyle without extra fees. The community amenities elevate your stay even further: relax in the sparkling pool, grill in the outdoor kitchen, or take advantage of exclusive deeded beach access to Siesta Beach—consistently ranked among the world's best beaches for its famous powdery quartz sand that stays cool underfoot, crystal-clear Gulf waters, and laid-back vibe. Inside, the unit is beautifully fully furnished and thoughtfully decorated with original art from a talented local artist—turn-key comfort and coastal charm. Whether you're planning a relaxing summer getaway, a family vacation, or an extended stay, this waterfront retreat delivers tranquility, convenience, and unparalleled access to Siesta Key's iconic shores and vibrant village life. If you're ready to claim your own slice of waterfront paradise this summer (or beyond), contact us today to schedule your private tour—availability won't last long!
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Teresa Ribaudo (941-376-4500)
1257 TREE BAY LN, SARASOTA, FL 34242
$10,00031 Days on yellowkey MLS ID: A4693183
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3882 Built: 1979Community: Tortoise EstatesSpa: YesSingle Family
Remarks: LOCATION, LOCATION, LOCATION!!! Available for a short term rental this expansive, water front, turnkey furnished, four bedroom plus a den, three and a half bathroom, single family home on the water on South Siesta Key is open to rent. Through the entrance on the first floor you enter into the family room with views of the pool and intracoastal waterway. The first level has a bedroom with queen sized bed, walk in closet and en-suite bathroom with a stall shower and a spacious living room with flat screen television. Laundry room with utility sink on this level. Up the open staircase leads to the main living floor with an open plan kitchen, dining room, living room combination and the den/office. The kitchen has a large island, plenty of counter and cabinet space for cooking/preparing, stainless appliances, breakfast bar and a wine fridge. All of these rooms overlook the pool and the intracoastal waterway. The primary bedroom has a king sized bed, comfortable sitting area, a water view, walk in closet and an en-suite bathroom that features a large garden tub, separate shower and double sinks. All bathrooms have been updated, and the bed sizes in all the two second floor bedrooms are queen sized. The home has a heated pool and hot tub, dock to tie up a boat which leads to the intercoastal waterway. Two car garage is not available for a renter but there is plenty of driveway parking. The owner will consider one small dog with a $300 refundable pet fee. WIDE OPEN FOR SUMMER/FALL 2026. SINGLE FAMILY HOME SIESTA KEY SARASOTA FLORIDA SEASONAL RENTAL
Listing Agent: C. Alison Hunter (941-587-5667)
8770 MIDNIGHT PASS RD #402B, SARASOTA, FL 34242
$8,0001087 Days on yellowkey MLS ID: A4574241
Remarks: Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location features the fourth-floor unit overlooking the intercostal waterway, just a short walk to the beach. The Siesta Key village and local dining are just a stroll away. The property has a beautiful community pool, tennis courts, shuffleboard, and more. The stylish decorum and nicely appointed finishes invite you to relax and unwind. TVs and internet for your convenience will help you not miss a beat. This property will not disappoint. Please call with any questions. $4,000.00 a month Starting May 1 2026. Unit is available for January, February, March at $8,000.00 per month plus sales tax. From April 2027 on the rent is $4,000.00 per month plus sales tax.
131 WHISPERING SANDS CIR #V33, SARASOTA, FL 34242
$3,95079 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
$2,95035 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
$5,50054 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
High School: Riverview High
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)
8625 MIDNIGHT PASS RD #506B, SARASOTA, FL 34242
$2,750102 Days on yellowkey MLS ID: A4684215
REDUCED by $600 (17.9%) on 05/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1222 Built: 1970Community: Bay Tree ClubCondo
Remarks: 2750.00 Monthly May through October 2026 ... Enjoy private access to the soft sand and tranquil setting of Turtle Beach - Siesta Key... Beautiful 5th-floor, fully furnished penthouse offering picturesque bay and treetop views in one of the most desirable Gulf-to-Bay communities on South Siesta Key. Move-in ready and designed for easy coastal living, this light-filled residence features an open split floor plan and tile flooring throughout. The updated kitchen boasts granite countertops and additional cabinetry, while both bathrooms feature new vanities for a fresh, modern touch. Enjoy sweeping bay views from the living space, along with the rare luxury of a privately owned beachside cabana—perfect for storing chairs, umbrellas, and keeping Siesta’s famous white sand outside where it belongs. Located in a quieter section of the Key, the home is still conveniently close to local restaurants and island activities. Take the Froghopper or the Free Ride Trolley to explore all of Siesta Key with ease. Bay Tree offers exceptional amenities including two pools (one on the beach side and one on the bay side), grilling and picnic areas, free boat slips for owners, kayak racks, on-site management, reserved owner parking, and ample guest parking. Walk to nearby dining, enjoy the bay, stroll the beach, or simply relax and take in the views—this property offers the very best of bayfront and beachfront living within one exceptional community. Rates: 3350.00 annually April through December 2026: Quoted rate applies January through April 2027: $6,500 per month, plus applicable taxes and fees.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
9393 MIDNIGHT PASS RD #605, SARASOTA, FL 34242
$2,495820 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)
5141 SAINT ALBANS AVE, SARASOTA, FL 34242
$3,20045 Days on yellowkey MLS ID: A4691423
REDUCED by $400 (11.1%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1131 Built: 1986Community: Siesta BeachSingle Family
Remarks: Available on an annual basis, come escape to relaxed island living in this elevated 2-bedroom, 2-bathroom Siesta Key cottage. Tucked away on a quiet, tree-lined street and set on a large lot with tropical landscaping and low maintenance, it offers both privacy and ease. Just 2 miles from Siesta Key Beach, it’s an easy bike ride or drive to the world-famous white sands, making beach days effortless. Inside, vaulted ceilings and warm wood interiors create a true Old Florida feel with an open, comfortable layout. The main level offers living and dining space, a functional kitchen, and a guest bedroom with a full bath, while the upstairs loft-style primary suite provides a private retreat. A screened porch overlooks a spacious yard, ideal for unwinding or working remotely. With room for a boat or RV, a storage shed, and no HOA restrictions, this is a fantastic option for your relocation to Siesta Key.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Anthony Dalesandro (941-504-5371)
9200 MIDNIGHT PASS RD #24, SARASOTA, FL 34242
$2,35056 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
$22,00037 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
$3,550951 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 Agent: Chrissie Cummings (772-532-8229)
9200 MIDNIGHT PASS RD #10, SARASOTA, FL 34242
$2,000463 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
$15,000198 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
$6,00038 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
$2,950308 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
$8,00041 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)
SARASOTA, FL 34242
$2,99543 Days on yellowkey MLS ID: A4691869
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 981 Built: 1973Community: Sandy Cove IiTownhouse
Remarks: Welcome to this Siesta Key Florida fully furnished town house for rent, located on the barrier island of Siesta Key Florida #1 beach in USA, made famous for its pure quartz sugar sand. A truly tropical beach front community Sandy Cove in Siesta Key with private fishing pier, small private beach and beautiful ocean view, and only one block from Siesta Key Village. A rarely available 2 bedroom two story townhouse for rent in Siesta Key Florida with enough space and privacy to suit year-round residents or your vacation home, those wishing to escape the harsh winter weather or anyone wanting a mesmerizing getaway location that offers a multitude of recreational and cultural activities. Take a look at this private Townhouse with stunning spanish tile floors throughout. Enjoy dolphins and manatees from your complexes own private gulf access and be amazed by the sea turtle nesting activities. One king size bed on first floor, two twin beds on 2nd floor with private balcony with ocean view. Launch your kayak for a quick paddle to the popular sand bars and return home to delight in the best sunset viewing around. Catch a wide variety of fish (snapper, grouper, flounder, etc.) off the private pier or take a short stroll into Siesta Key Village for a little shopping, a quick lunch or the best fine dining that the Sarasota area has to offer. You will love the option of your own private fishing pier or only a block to the Siesta Key public beach for collecting sea shells and enjoying the world-renown beautiful quartz sand beach. The downstairs has the master bedroom, family room, kitchen with newer cabinets and quartz countertops as well as some new appliances and dining nook. Also downstairs is the full bathroom. Upstairs, you will find two distinct loft spaces with two twin beds with half bath in between as well as your private balcony. There is a view of the gulf from every room in the house. Enjoy the endless sunsets and the waves crashing against the shoreline from this light and bright townhouse. A private path will lead you to the shores of jewel toned waters of the Gulf of Mexico and Big Pass, where you can view the endless array of marine life, fish from the private pier, or just sit back and relax and watch the boats sail off into the sunset. In this unit, there is a private balcony on 2nd floor with beautiful gulf view, and private screen patio off Master Bedroom with gulf view, this unit also has brand new refrigerator, brand new dishwasher and high end German Miele build in Oven, exhaust fan and Miele cooktop. There are two private parking spots in front of this unit for four our unit 109 plus many guests parking spots in front of this unit. Ocean view from this townhouse is amazing! You will have ocean view from every room (ocean view from family room, ocean view from master bedroom, ocean view from upstairs loft bedrooms, ocean view from kitchen and even the upstairs bathroom has the ocean view), this is a very unique ocean front view townhome! You'll never miss a sunset again! You can drink your wine and enjoy the sunset at your outdoor patio, and relax after a long date! This town home has patio outside of the master bedroom, balcony from upstairs loft, and patio from breakfast room and they all have ocean view. Watch the gorgeous sunsets right from your own balcony and patio. Fishing pier for fishermen or just watching the boats. You can park two cars in front of this unit
Listing is courtesy of: JJF REALTY INC (904-891-6897)
Listing Agent: Matthew Fehniger (904-891-6897)
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