Location: Sarasota , 34242
Do Not Show Listings
4946 COMMONWEALTH DR, SARASOTA, FL 34242
$5,000295 Days on yellowkey MLS ID: A4657231
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2080 Built: 1972Community: Siesta BeachSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Available as a monthly rental in May, August, September, October, November and December 2026 only! Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock, watching for playful manatees and jumping fish, or simply basking in the sunshine by your private pool. With ample outdoor space for lounging, dining, or even trying your hand at fishing, this backyard oasis is your personal paradise. Inside, the home offers a beautifully appointed, light-filled space. The primary bedroom boasts a comfortable King bed and an en-suite bathroom, while the second bedroom features a Queen bed, and the third provides flexible sleeping with two Twin/Single beds. The fully equipped kitchen is ready for family dinners, though with the vibrant Siesta Key Village near, you might prefer to explore the array of locally owned restaurants, cafes, and lively bars. The unbeatable location means you're not only steps from delicious dining and entertainment, but also just a short 3-minute drive (or a fun bike/golf cart ride, a local favorite!) to the world-famous Siesta Key Beach, consistently ranked among the best in the USA. Please note: If you are bringing a pet, there is a $250 pet fee (per pet). We encourage you to inquire about the specific pet policy applicable to your reservation for clarification, including how and when the pet fee will be collected.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
5157 SANDY BEACH AVE, SARASOTA, FL 34242
$6,00011 Days on yellowkey MLS ID: A4689130
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2288 Built: 1992Community: Siesta BeachSpa: NoSingle Family
Remarks: Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee at LeLu Coffee Lounge. 4 bedrooms and 2.5 baths brings you back inside with a large open living room and kitchen with breakfast bar. The master suite on the main level with en-suite bathroom with access to the pool. Upstairs you have 3 additional bedrooms.
Listing is courtesy of: M&M PROPERTY MANAGEMENT GROUP (941-320-4287)
Listing Agent: Joe Meszaros (941-320-4287)
5400 OCEAN BLVD #10-02, SARASOTA, FL 34242
$10,00012 Days on yellowkey MLS ID: A4688970
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 936 Built: 1970Community: TerraceCondo
Remarks: Welcome to The Terrace 10-2 on Siesta Key, a fully renovated 10th-floor beachfront condo offering some of the most breathtaking panoramic views on Florida’s Gulf Coast. Designed by the renowned architect Frank Folsom Smith, The Terrace stands as one of Siesta Key’s most architecturally significant landmarks, combining mid-century sophistication with timeless coastal beauty. The Space This 1-bedroom, 1-bath luxury condo has been meticulously redesigned for modern comfort and effortless relaxation. The open-concept floor plan connects the sleek kitchen, dining, and living areas—each surrounded by wraparound windows that reveal 280° views of turquoise waters and quartz sand. • Fully renovated interiors with custom finishes • Concrete and wood-paneled ceilings add warmth and architectural texture • All-new stainless-steel appliances • Granite countertops and bar seating for three • Dining table for four just off the kitchen • Work desk with ocean views • Spacious sectional sofa and Smart TV in the living area • Smart TV on the patio, perfect for enjoying the game with the sound of the waves • Three private balconies with outdoor seating and panoramic views of Siesta Key Beach, Lido Key, and downtown Sarasota The primary bedroom features a plush king bed, large TV, and floor-to-ceiling glass that frames the coastline from sunrise to sunset. The bathroom includes a walk-in shower and elegant finishes throughout. Amenities • Direct beach access from The Terrace grounds • Heated oceanfront pool with sundeck and loungers • Private parking for one car • High-quality linens and towels • Beach gear provided Location Situated at the corner of Ocean Boulevard and Beach Road, The Terrace offers the closest proximity to Siesta Key Village of any beachfront condominium, just steps from restaurants, live music, and boutique shopping. From your balcony, enjoy views stretching from Venice Pier to Anna Maria Island, with Sarasota’s city skyline sparkling in the distance. Rental Details • 60-day minimum stay • Board application and approval required Experience the best of Siesta Key, where modern design meets classic coastal living. The Terrace by Altez Vacations invites you to wake up to endless horizons and fall asleep to the sound of the surf. Rates: 10,000 April - December: 16,000 January - March Rate includes all utilities and taxes 2-Month Minimum **Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best serve your request
Listing is courtesy of: ALTEZ VACATIONS, LLC (941-349-9580)
Listing Agent: Sean Altice (323-363-4107)
8625 MIDNIGHT PASS RD #305B, SARASOTA, FL 34242
$4,700112 Days on yellowkey MLS ID: A4670970
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 697 Built: 1970Community: Bay Tree ClubCondo
Remarks: Siesta Key! Newly renovated and fully furnished 1BR/1BA condo set in a relaxed, resort-style waterfront community on Siesta Key. This gulf/beach-to-bay condominium features expansive boat docks (no extra usage fee), two heated pools (bay & gulf/beach side), private/individual gulf/beach side cabanas, kayak racks, 2 BBQ grill patios, exquisite sunrises & sunsets & so much more ~ everything a boating enthusiast or beach lover could dream of. Located in the coveted Bay Tree Club on South Siesta Key, this is your chance to embrace coastal life at its finest, whether you're exploring the Gulf by boat or lounging on sugar-sand beaches. The pools & grill areas provide idyllic locations for all gatherings. This freshly remodeled condo features a generous sized living room with a French/Juliet balcony overlooking the bay side heated pool & lush grounds with some views of the Sarasota Intracoastal Waterway. The dining area has a pass-through access to the updated designer kitchen featuring quartz countertops & new self-closing cabinets/drawers The primary bedroom has a large closet providing ample storage. Along with the foyer closet, you will have room for all your possessions. Don't forget the beach side cabana for your gear. Renovated full bath with a tub completes. Each building is equipped with elevators and laundry rooms (coin-op) on every floor ensure everyday comfort is never out of reach. During your stay, explore all the unmatched amenities, nearby restaurants & shops. Bonus is The Breeze Trolley stop just outside. Hop aboard and enjoy free rides to & from Siesta Beach (recently voted #1 in the US & #4 Globally) and Siesta Village. Stay aboard to Downtown Sarasota where you can transfer to the Bay Runner for jaunts to iconic St. Armands Circle & beyond. Life is good here ~ Welcome to your Coastal Oasis Getaway! IN Season, January-April, 5300/month. OFF Season, May-December, $4700/month. Weekly option available for off season. Sorry no pets. Owner/Agent.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Aurelia Gilbert (203-451-3178)
1256 RIEGELS LANDING DR, SARASOTA, FL 34242
$6,500382 Days on yellowkey MLS ID: A4646919
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2168 Built: 1986Community: Riegels LandingSingle Family
Remarks: This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full bath, with its only living room are located on the ground floor with private patios front and back. Think in-law suite. In addition an office/bonus/exercise room is located on the ground floor. The third floor host a loft with a full bath and entertainment area. A full wrap around deck covers the back of the home. The master and guest have a private deck as well. 2 car garage with built in storage. Additional parking left and right side of driveway. House comes fully furnished. 8 month min. lease, available today.
Listing is courtesy of: STARLINK REALTY INC (239-693-7263)
Listing Agent: Christopher Davenport (678-776-2617)
8302 MIDNIGHT PASS RD, SARASOTA, FL 34242
$6,00017 Days on yellowkey MLS ID: A4687881
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1500 Built: 1953Community: Ocean ViewSingle Family
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Available Monthly: Mid May through October 2026 Experience the best of island living in this beautifully restored, better-than-new 3-bedroom, 2-bath single-story pool home with a separate office, nestled in the peaceful and tropical setting of South Siesta Key. Tucked away on the serene Heron Lagoon, this home offers an unforgettable coastal retreat perfect for those relocating, remodeling, or simply seeking a private escape. Wake up to soothing water views and spend your days lounging by the private heated pool and spa, fishing or kayaking from the dock, or relaxing in the lush, landscaped backyard surrounded by nature. Heron Lagoon is a hidden gem, alive with wildlife and tranquil views that define true Siesta Key living. The bright and sunny interior has been completely renovated with modern updates, offering a stylish yet comfortable coastal vibe. Enjoy the open-concept living space, updated kitchen, dedicated office, and tranquil bedrooms that make it easy to feel at home. Located just minutes from Turtle Beach, a local marina, and a public playground, you’ll also enjoy easy access to the Siesta Key Trolley, which connects you to the world-famous Siesta Key Beach and the vibrant shops and restaurants of Siesta Village. The surrounding streets are perfect for biking or strolling under shady, tropical canopies. Whether you're transitioning between homes, looking for a temporary residence while building or remodeling, or seeking a monthly getaway, this special home offers the perfect blend of privacy, comfort, and island charm. Let the stress melt away... the soul-soothing lifestyle of Heron Lagoon awaits. This rare rental opportunity will exceed your expectations. Call to schedule a private showing today.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
5855 MIDNIGHT PASS RD #426, SARASOTA, FL 34242
$5,000954 Days on yellowkey MLS ID: A4581930
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1976Community: Harbor Towers Y & RCondo
Remarks: Listing reflects peak season rate. Available peak season months: January 2027-April 2027. Off season rates start at $5,000. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot, you'll feel the resort vibe. Step into the beautifully remodeled lobby and take the elevator to the fourth floor, where the inviting blue hues of Turquoise Turtle welcome you to paradise. Inside, you'll find modern beach decor and an updated galley kitchen, designed for your comfort. The primary bedroom features a king-sized bed, while the second bedroom offers a comfortable queen bed. A sleeper sofa in the living area accommodates two additional guests, allowing the condo to comfortably sleep up to 6 guests. The two bathrooms are clean and functional, and the split floor plan ensures privacy for all guests. Step out onto your private balcony and enjoy views of the world-famous Siesta Key Beach directly across the street! You'll be just minutes away by foot, and a quick trolley, bike, or golf cart ride will take you to Siesta Key Village's delicious restaurants and vibrant shops. Harbor Towers boasts an array of amazing amenities, including two heated pools, three Har-Tru tennis courts, and an outdoor patio overlooking one of Siesta Key's largest marinas. Notably, the community is located directly on the Intracoastal Waterway, and for boat enthusiasts, you are able to register with the HOA to dock your boat right on-site. The community also offers convenient washers and dryers on every floor and a fitness room. Don't wait – book your ultimate Siesta Key vacation at Turquoise Turtle today!
131 WHISPERING SANDS CIR #V33, SARASOTA, FL 34242
$4,75025 Days on yellowkey MLS ID: A4687180
Bed: 2 Bath: 2.0 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)
7006 MIDNIGHT PASS RD, SARASOTA, FL 34242
$1,70058 Days on yellowkey MLS ID: A4683279
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 850 Built: 1978Community: Point O Rocks Terrace AddHalf Duplex
Remarks: Welcome to your beach retreat on Siesta Key at 7006 Midnight Pass Rd #4. This bright and inviting 1-bedroom, 1-bath residence offers approximately 850 square feet of easy, coastal living with new paint throughout. The open living and dining area is finished with ceramic tile flooring for effortless maintenance—perfect for the beach lifestyle—while central air conditioning keeps everything comfortable year-round. The spacious bedroom easily accommodates a king-size bed. Enjoy indoor-outdoor living on the screened patio, which opens to a fenced backyard with a new paver walkway, ideal for grilling and relaxing after a day at the beach. Additional conveniences include on-site laundry, extra storage for beach gear, and covered parking. Close to Siesta Key’s renowned dining and shopping, with upper and lower units available; pets considered with approval and no smoking
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Anthony Almengual (941-807-5626)
6006 MIDNIGHT PASS RD #15, SARASOTA, FL 34242
$7,500397 Days on yellowkey MLS ID: A4644906
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 600 Built: 1960Condo
Remarks: No roads to cross to get to the beach! Just listed- This clean, updated, cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your suit and enjoy your stay now!!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
6480 MIDNIGHT PASS RD #506, SARASOTA, FL 34242
$12,000399 Days on yellowkey MLS ID: A4644593
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979Community: Siesta BreakersCondo
Remarks: Siesta Key's beautiful coastline offers you the chance to enjoy your dream vacation in this fantastic 2-bedroom ocean-view condominium. Situated directly on the beach and across the street from the South Village, you’ll be mere steps away from both the beautiful water and a vast array of destinations. The South Village includes a full-service grocery store and numerous restaurants, ice cream shops, shopping spots and live entertainment venues to choose from all within a 5–10-minute walk. As a guest, you'll delight in the array of traveler favorites, including a refreshing outdoor pool, complimentary high-speed WiFi, and the convenience of a washing machine and dryer in the unit. Unwind in the evenings with a movie on the smart TV, or curl up with a good book. The fully stocked kitchen, complete with a stove, oven, refrigerator, and dishwasher, invites you to unleash your culinary creativity. Savor your meals at the dining table, or step out onto the balcony and enjoy the breathtaking ocean views. Indulge in the essentials, such as plush towels, basic toiletries, and an iron and board, ensuring a comfortable and hassle-free stay. With air conditioning, heating, and linens provided, you'll be able to relax in complete comfort. A sleeper sofa in the living room is a bonus when you want to sleep six guests in the condo. Embrace the great outdoors with the beach loungers, towels, and outdoor furniture, perfect for soaking up the sun or enjoying a leisurely stroll along the shore. And when you're ready to explore, the desk and chair in the office space provide the perfect spot to plan your adventures. Immerse yourself in the beauty of Siesta Key and create lasting memories at our exceptional beachfront condo!
4660 OCEAN BLVD #P1, SARASOTA, FL 34242
$3,400136 Days on yellowkey MLS ID: A4673816
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971Community: Sea Village / Siesta KeyCondo
Remarks: Long term rental turnkey furnished waterfront condo in the desirable Sea Village community. Enjoy stunning views of Big Pass and the Gulf, plus easy access to the community pool. The home features travertine flooring, crown molding, hurricane-rated sliders, plantation shutters, and an open living/dining layout. The kitchen includes wood cabinetry, granite countertops, a breakfast bar, and quality appliances. The primary bedroom offers lanai access and an updated en-suite bath with dual sinks and a walk-in shower. The guest bedroom and bath are also well-appointed. A spacious lanai with travertine flooring and clear-view screening extends to an outdoor patio with wide water views. Impact-rated glass throughout for added peace of mind. Located on the north end of Siesta Key, just moments from Siesta Key Village, beaches, dining, and Sarasota amenities—an ideal coastal rental.
Listing Agent: Nelson Reyes (813-843-7003)
1355 S PORTOFINO DR #103, SARASOTA, FL 34242
$5,00058 Days on yellowkey MLS ID: A4682516
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1389 Built: 1975Community: Siesta Harbor IiiCondo
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: DANIELLE GLADDING & CO. REALTY (941-539-8535)
Listing Agent: Alison Kanter (941-306-9786)
4237 HIGEL AVE, SARASOTA, FL 34242
$6,55030 Days on yellowkey MLS ID: A4686838
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1835 Built: 1946Community: Cocoanut BayouSingle Family
Remarks: Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking Cocoanut Bayou. Completely private by its original growth of lush tropical landscaping, this property is captivating for all your senses. This 1,500 sqft home was built in 1946 and will wow you from the door with its original decor. Mexican tile floors are throughout the entire house with handmade ceramic Mexican accents. The main living room has built-in cabinets and a large fireplace to add candles and create ambiance. The kitchen comes equipped with stainless appliances and is open to the dining and living area. There is a split floor plan with two beds on one side and the master suite on the other. Enjoy the lifestyle with plenty of outside living, a screened-in lanai, an open-air patio, a pizza oven/fire pit, and a pool. Bonus~ separate, new inside laundry room that can be an extra guest room, art den, or man cave. For water enthusiasts, take your pick boating, paddle boarding, and jet skis, equipped with a private dock (no lift) for your water sport pleasure. Launch your kayak from the pier and feel the restorative nature of calm waters and mangrove tunnels. Resident Benefits Package Included for all Tenants: The Relax Property Management Resident Benefits Package (RBP) delivers savings and convenient, professional services that make taking care of your home second nature. By applying, tenants will be enrolled and pay the applicable cost of $50 additional/monthly; this is part of the lease and payable with rent.
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Joleisy Machado-Gonzales (941-915-9251)
8625 MIDNIGHT PASS RD #506B, SARASOTA, FL 34242
$3,35048 Days on yellowkey MLS ID: A4684215
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1222 Built: 1970Community: Bay Tree ClubCondo
Remarks: 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: $6,000 per month, plus applicable taxes and fees.
20 WHISPERING SANDS DR #903, SARASOTA, FL 34242
$12,0001142 Days on yellowkey MLS ID: A4562777
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Community: Whispering Sands Sec 6Condo
Remarks: Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of life behind. As you exit the elevator to your floor, you will be surrounded by gorgeous views of the village, the bay and the gulf! Once inside, you will have full Gulf views from just about every room. All tile through-out, the main living area is well outfitted with comfortable seating, a custom-built cabinet housing a fireplace and large screen TV, great for movie night! There is dining for six or more with elegant custom lighting, and a breakfast bar with seating for four. The kitchen is a cook's dream featuring Quartz counters, high-gloss cabinets, newer appliances and additional eating space. The primary suite offers a king bed, and a walk-in closet. The primary bath has dual sinks and a lovely custom shower. The guest bedroom has a Queen bed, and there is a beautiful guest bath. Both the main living area and the primary bedroom feature sliders out to the patio, overlooking the azure water of the Gulf, where you can sip your morning coffee, or take in a fabulous sunset! Not only do you have 800 waterfront feet of private beach, but you also have your choice of two sparkling heated swimming pools, one on the beach and one overlooking a peaceful lagoon. This immaculately maintained community has it all, you have a Tiki Hut on the beach, outdoor grills, shuffleboard, a clubhouse with full kitchen and a fitness room. Just MINUTES to SIESTA KEY VILLAGE, take the private gate, located just behind Davidson's Drugs, to the Village for all your shopping and dining needs. Don't wait to reserve this amazing rental, available for longer term rentals as well as short term. Welcome to paradise! (Booked January through end of March 2026)
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)
Listing Agent: Stephanie Deshaies (941-780-3229)
9397 MIDNIGHT PASS RD #501, SARASOTA, FL 34242
$5,000126 Days on yellowkey MLS ID: A4674922
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1975Community: Pointe On Midnight PassCondo
Remarks: One or more photo(s) has been virtually staged. Siesta Key Seasonal Retreat at The Pointe is available beginning April 18, 2026, with a 3-month minimum stay required. Available April through Mid December 2026... Not Available for Season 2027 ... Attractively priced, this waterfront property offers an exceptional opportunity to spend your winter surrounded by stunning water views on the southernmost tip of Siesta Key. The Pointe features breathtaking vistas of Little Sarasota Bay, the lagoon, and the Gulf of Mexico. Enjoy mornings in your sunlit kitchen overlooking the Gulf or relax on the spacious enclosed, air-conditioned balcony while watching birds and boats drift by. The community offers outstanding amenities, including a heated pool with spa, lighted tennis courts, fitness and community rooms, a clubhouse with kitchen, kayak and fishing access, an outdoor pavilion, and on-site management. Just a 10-minute walk brings you to Turtle Beach, where you can enjoy swimming, shelling, playgrounds, restrooms, a boat launch, and picnic areas. Nearby dining includes Turtle Beach Pub, Ophelia’s on the Bay, and Turtles on Little Sarasota Bay, with Southbridge shops and restaurants also close by. The Siesta Key trolley provides easy access to the Village, ensuring convenience and a truly effortless seasonal getaway. Whether you seek sun, sand, or serene waterfront living, this delightful condo at The Pointe offers an unforgettable stay on beautiful Siesta Key.
8710 MIDNIGHT PASS RD #405, SARASOTA, FL 34242
$4,750 MLS ID: A4630124
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1980Community: TortugaCondo
Remarks: AVAILABLE APRIL 2026. This is a great opportunity to live on the beach. Your new home is located on the 4th floor. Open plan, with large tile throughout. The home is furnished with an equipped kitchen. Grab your plate and fork because this property is having your cake and eating it too... Just bring your suitcase and you are set. Not too many condos have this, but your 2-bedroom 2-bath is a split plan. Wait until see the grounds and just a few steps to the Gulf. Very easy to show. The owners are looking for annual lease. But the winter rental PRICES will increase for winter months. Easy to show!!!
Listing is courtesy of: AUDREY RAIN RENTALS, INC (941-487-7162)
Listing Agent: Anthony Deluca (941-685-6001)
9397 MIDNIGHT PASS RD #405, SARASOTA, FL 34242
$2,600 MLS ID: A4663823
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1975Community: Pointe On Midnight PassCondo
Remarks: **NOW AVAILABLE EITHER AS A LONG-TERM OR SHORT-TERM RENTAL (minimum 3 months).** Here’s is your chance to live on the SOUTHERNMOST TIP OF SIESTA KEY and enjoy STUNNING SUNRISES & SUNSETS all year long. This WATERFRONT RENTAL is located at The Pointe, the CLOSEST CONDO complex to MIDNIGHT PASS! This one-of-a-kind gated community encompasses over 5+ acres of PRIME WATERFRONT real estate and is loaded with amenities including tennis, pickleball, fitness center, heated lap pool, spa, dry sauna, kayak launch, clubhouse and more. Boat docks are also available for a small fee on a first come first serve basis. Rather go to the beach? No problem…Turtle Beach access is just a half-mile away. And let’s not forget, just a few miles up the road are all the amazing restaurants and shops of Siesta Village. The first thing you’ll notice when you enter this turnkey-furnished, 2bed/2bath condo, is how the living area leads right out to an expansive 30-foot lanai overlooking Little Sarasota Bay and the Jim Neville Nature Preserve…a perfect spot for entertaining or just sitting back and enjoying the view and the wildlife. The primary bedroom also has access to the lanai and features an ensuite bathroom, finished closets, and of course, spectacular sunrise views. Engineered hardwood floors throughout give the home a cozy, beachy feel. Unlike other condos in the area, a washer/dryer is conveniently located within the unit. Recent updates include 5 new ceiling fans, new blinds, new range, newer dishwasher, and new furniture in the dining room and living room. AC was replaced in 2019. There is also additional storage space on the ground floor for all your beach and boating gear. Sorry, no pets allowed. Rental applications must be received 21 days prior to any occupation. **Long-Term Rental (minimum 7 months) = $2600/month ~ Short-Term Rental (minimum 3 months) = $6500/month.
Listing is courtesy of: UKEEPCOMMISSION REAL ESTATE (941-465-9206)
Listing Agent: Adam Waxler (941-465-9206)
1257 S PORTOFINO DR #36, SARASOTA, FL 34242
$5,000 MLS ID: A4125928
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1968Community: Siesta Harbor ICondo
Remarks: Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open kitchen and remodeled bathrooms are some of the perks in this waterfront unit. Sit on your lanai and watch the boats go by as you sip your morning coffee. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. This is a 55+ community which means one renter in the party must be over 55 years of age. No pets and no smoking please. 1 car reserved parking space.
Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)
Listing Agent: Margaret Young (941-359-3435)
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