Location: Sarasota, 34242
Do Not Show Listings
4830 HIGEL AVE, SARASOTA, FL 34242
$6,500Listed 05/29/2026 3:07PM MLS ID: A4694659
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1724 Built: 1957Community: Harmony SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: More pictures to come, waiting for the rest of the furniture to arrive. Florida charm at it’s best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the Sarasota School of Architecture. The home is on 1/3 of an acre on the Grand Canal with a dock and kidney-shaped heated pool. The new hardwood flooring and new impact windows make this home bright and inviting with volume ceiling space. The living room and kitchen offer delightful sunset views. This house is great for entertaining with a dry bar and amazing sunset views for everyone to relax. The two front bedrooms have French doors that lead out to a front screened porch that has a Zen feel--perfect for meditation or relaxation. The grounds are filled with exotic indigenous plants and trees. Dockage will accommodate a small boat, 23ft or smaller, or jet skis. Great getaway on Siesta Key, minimum 30 days require. The off Season rate is $6500 per month and Prime season rate is $10,500 per month Dec thru April
Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)
Listing Agent: Toyia Youtzy (941-915-7926)
4237 HIGEL AVE, SARASOTA, FL 34242
$5,99572 Days on yellowkey MLS ID: A4686838
REDUCED by $255 (4.1%) on 05/29/2026
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)
115 EDMONDSON AVE, SARASOTA, FL 34242
$15,0004 Days on yellowkey MLS ID: A4694729
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 3248 Built: 2002Community: Siesta Rev OfSpa: YesSingle Family
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Experience luxury coastal living just moments from world-famous Siesta Key Beach. This exceptional 5-bedroom, 5-bath residence offers approximately 3,248 SF of beautifully designed living space with an open and inviting floor plan perfect for entertaining and everyday comfort. The home features spacious bedrooms, abundant natural light, multiple gathering areas, two full kitchens, two laundry rooms, imported Italian tile throughout, USB-equipped outlets throughout the home, and designer dimmable lighting that enhances the modern coastal ambiance. Recent major upgrades include a new roof and impact-rated windows and doors for added peace of mind and energy efficiency. Designed for both relaxation and entertaining, the property offers seamless indoor/outdoor living with a heated pool and spa, along with a large lanai overlooking the pool and beautiful open water views. Boating enthusiasts will appreciate the large dock, private boat lift, and direct easy access to the Gulf of America for exceptional fishing and boating adventures with no fixed bridges. Enjoy a short 5-minute kayak ride to a popular nearby sandbar, making this property a dream location for boating enthusiasts, beach lovers, and those seeking the ultimate waterfront entertainment lifestyle. Ideally located just 5 minutes from world-renowned Siesta Key Beach and walking distance to Shell Rd Beach, this home places you near some of Sarasota’s most desirable coastal destinations. Located in one of Sarasota’s most sought-after island neighborhoods, you are also minutes from waterfront dining, boutique shopping, marinas, and vibrant local attractions. Whether you are seeking a primary residence, luxury vacation retreat, or income-producing investment property, this home offers the ultimate Siesta Key waterfront lifestyle.
Listing is courtesy of: SARASOTA INTERNATIONAL REALTY (941-227-5555)
Listing Agent: Wally Sabrii (941-313-9999)
5624 CAPE LEYTE DR, SARASOTA, FL 34242
$15,00091 Days on yellowkey MLS ID: A4684371
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3126 Built: 1963Community: Siesta IslesSpa: NoSingle Family
Remarks: Prime Siesta Key Waterfront Retreat – Fully Furnished & Walk to the Beach Welcome to 5624 Cape Leyte Drive, a fully furnished luxury beach retreat just a short walk to world-famous Siesta Key Beach. This turnkey property showcases refined coastal elegance with designer furnishings, Italian tile and quartz finishes throughout, and spa-inspired bathrooms featuring rainfall showers. Every detail reflects upscale craftsmanship and modern island sophistication. Step outside to your private backyard oasis featuring a large resort-style pool, outdoor shower, and BBQ entertaining area — perfect for hosting guests after a day at the beach. Located in one of Siesta Key’s most desirable walkable neighborhoods, you’re just steps from beach access, restaurants, cafes, and island attractions. Park once and enjoy everything on foot. Ideal as a high-performing short-term rental investment or a private island escape. Prime walkable luxury properties near Siesta Key Beach consistently command strong rental demand and premium rates.
31 LANDS END LN, SARASOTA, FL 34242
$15,000504 Days on yellowkey MLS ID: A4635483
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2743 Built: 1967Community: Lands EndSingle Family
Remarks: Turnkey Waterfront Retreat on Siesta Key – A Fully Furnished Coastal Paradise! Discover the ultimate coastal lifestyle in this fully furnished, move-in-ready 4-bedroom, 3-bathroom waterfront retreat on the north end of Siesta Key. Perfectly situated just minutes from Sarasota’s top attractions, this home blends luxury, tranquility, and convenience. Set on 0.4 acres of deep sailboat water, the property boasts 68 feet of waterfrontage on Bayou Louise and a 20-foot dock with direct, bridge-free access to Big Pass and the Gulf of Mexico. Spend your days boating, fishing, or enjoying sunsets over the Gulf. A quick 5-minute boat or kayak ride leads to a vibrant sandbar, ideal for fun and relaxation. Surrounded by neighboring homes valued at $20+ million, this property offers a rare opportunity for luxurious waterfront living. Tropical landscaping creates a serene oasis with a spacious deck, an outdoor grill, and a gazebo for entertaining or unwinding after a day on the water. Inside, the home exudes modern coastal charm. The gourmet kitchen features quartz countertops, stainless steel appliances, and designer touches, while the family room offers stunning water views through impact sliding doors. The primary suite is a private retreat with its own entrance, a custom walk-in closet, and spa-like finishes. An additional in-law suite with a private entrance provides added flexibility and convenience. This exceptional property is just a 5-minute walk to Shell Road Beach, 3 miles from Siesta Key Village, and 3.3 miles from the world-renowned Siesta Key Beach. The sandbar is a short 5-minute kayak ride, while downtown Sarasota and St. Armands Circle are just a quick drive away. Fully equipped with linens, beach towels, bicycles, cookware, a coffee maker, LED lighting, and more, this home ensures a seamless and comfortable stay. Available for both short- and long-term rentals, it’s perfect as a luxurious personal retreat, an entertainer’s dream.
4660 OCEAN BLVD #G1, SARASOTA, FL 34242
$3,40029 Days on yellowkey MLS ID: A4692031
REDUCED by $100 (2.9%) on 05/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971Community: Sea VillageCondo
Remarks: Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added convenience. Enjoy the ease of your own in-unit washer and dryer. Plus, your furry friends are welcome here! Amenities include two pools, grilling area, lush green spaces, and a fishing pier. Enjoy your morning coffee from the covered lanai with potential views of the bright turquoise water and occasional dolphin sightings. The vibrant North Village, with its unique boutiques, fantastic restaurants, and live music, is just a short bike ride or stroll away.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
1308 OLD STICKNEY POINT RD #WP3, SARASOTA, FL 34242
$15,000114 Days on yellowkey MLS ID: A4681452
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3524 Built: 2002Community: Marina Del SolCondo
High School: Riverview High
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)
5628 CAPE LEYTE DR, SARASOTA, FL 34242
$10,00029 Days on yellowkey MLS ID: A4692170
INCREASED by $1,000 (11.1%) on 05/07/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2030 Built: 1963Community: Siesta IslesSpa: NoSingle Family
Remarks: Your cozy getaway awaits in Siesta Key at this terrific house. With three bedrooms featuring a king, queen, and full bed, guests find plenty of space to relax. The large heated pool gives you an amazing space for relaxing after a day at the beach which is just steps away. You also have a large gazebo adjacent to the pool to get out of the sun and showcase you BBQ skills. Whether you’re unwinding after a day of adventure or enjoying a quiet evening indoors, this soothing retreat offers a fantastic place to recharge. We look forward to hosting you at our place.
Listing is courtesy of: REALTY EXECUTIVES GALLERY (941-376-8769)
Listing Agent: Troy Jenkins (941-376-8769)
4822 OCEAN BLVD #5F, SARASOTA, FL 34242
$3,30081 Days on yellowkey MLS ID: A4685737
Bed: 2 Bath: 2.0 Gar: 9 Liv Area Sq Ft: 1435 Built: 1973Community: Siesta TowersSpa: NoCondo
Remarks: Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass doors that lead to a massive private balcony spanning both the living room and the primary bedroom. Step outside to take in sweeping views of the Gulf—perfect for morning coffee, sunset watching, and even spotting dolphins while you do the dishes. This residence offers 2 bedrooms and 2 full bathrooms, along with generous storage throughout. Free community laundry is conveniently located just down the hallway, and the unit has recently been painted, giving it a fresh, clean feel. Residents of Siesta Towers enjoy extensive amenities including a secure building, large heated Gulf-front pool, private park area, club room with full kitchen, fishing pier, BBQ grills with dining pier, fish/tackle room, bike storage, and a library. Located on the north end of Siesta Key, you are just a short walk to Siesta Key Village with its lively restaurants, shops, and entertainment. World-famous Siesta Beach is also nearby. Off the island, you are only minutes from Sarasota where you can enjoy theaters, opera, Marie Selby Botanical Gardens, museums, and the marina. How many times in life do you get the chance to live right on the beach? Call today to schedule your showing. Note: This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details.
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Cody Smith (404-991-0209)
726 BIRDSONG LN, SARASOTA, FL 34242
$5,52510 Days on yellowkey MLS ID: A4694343
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1822 Built: 1972Community: Siestas Bayside Waterside SouthSingle Family
Remarks: AVAILABLE after June 1, 2026! Enjoy your own slice of paradise on World Famous Siesta Key! This beautifully renovated turnkey 3-bedroom, 2-bath heated pool home is just a short distance from the #1-rated beaches and the charming shops and restaurants of Siesta Key Village. Whether you're here for million-dollar sunsets, endless watersports, the famous Sunday Drum Circle, or simply peaceful days spent relaxing by the pool, this home is the perfect place to settle in and enjoy it all. The home comfortably sleeps 6-8 guests, with a king bed in the primary bedroom, a queen bed in the second bedroom, and a twin bed with a pull-out trundle in the third. The full-sized chef’s kitchen overlooks the pool, while two separate gathering spaces provide plenty of room to relax, unwind, or entertain. Outside, the fabulous outdoor living space invites you to soak up the Florida sunshine in your own private retreat. 30-day minimum term only. Jan-April = $9,200, May-October = $5,525, November = $6,300, December = $7,350. 13% tourism tax added to all leases under 6 months. Just bring your toothbrush and sunscreen! SORRY, NOT AVAILABLE AS AN ANNUAL RENTAL. Currently booked Dec 15, 2026-Mar 15, 2027.
Listing is courtesy of: TNG REAL ESTATE (941-773-9599)
Listing Agent: Scott Nold (941-773-9599)
SARASOTA, FL 34242
$7,85010 Days on yellowkey MLS ID: O6409341
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976Community: Harbor Towers Y & RCondo
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
$4,5001230 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)
3919 ROBERTS POINT RD, SARASOTA, FL 34242
$9,97511 Days on yellowkey MLS ID: A4694087
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2497 Built: 2016Community: Siesta Rev OfSpa: YesSingle Family
Remarks: Located on Siesta Key with just a 3 minute walk to Shell Beach, this 2-story home is available NOW & FURNISHED for an ANNUAL LEASE. The kitchen flows seamlessly with an OPEN LAYOUT into the expansive living and dining areas filled with NATURAL LIGHT from the large sliding glass doors opening to the SCREENED-IN LANAI. The POOL & HOT TUB/SPA, also screened-in, are framed by lush TROPICAL LANDSCAPING including lemon, avocado, banana and mango trees! The COVERED PATIO space is ideal for sunset dinners, quiet mornings, or year-round relaxation in the coastal breeze. A SUN SHADE SCREEN is installed as well for maximum outdoor comfort. Plus a fully equipped OUTDOOR KITCHEN - perfect for entertaining. Inside your kitchen, enjoy: >> Thermador Stainless Steel Appliances >> Bar Fridge >> Shiloh Cabinetry >> Quartz Countertops >> Kitchen Island >> Breakfast Bar >> A whole house WATER FILTRATION SYSTEM with ULTRAVIOLET LIGHT The spacious primary suite on the 1st floor offers: >> Dual Walk-In Closets >> Dual Vanities >> luxurious Jacuzzi Tub >> Walk-In Shower 2 bedrooms share the 2nd floor. This home is concrete block construction on the first floor and a framed second floor with durable synthetic siding. It has IMPACT WINDOWS AND DOORS plus is equipped with a WHOLE HOUSE GENERATOR. There is a 2 CAR GARAGE plus a LAUNDRY with Washer & Dryer included. >> Siesta Key Village shopping and restaurants are a few minutes drive or bike ride >> 3 minute walk to Shell Beach >> Near the North Bridge with direct access to Publix, CVS, Barnes & Nobles, and more! >> 10-15 minutes drive from Mid Town & Downtown Sarasota SCHOOL DISTRICT: Phillippi Shores Elementary, Brookside Middle School, & Sarasota High School
Listing is courtesy of: KEYRENTER SARASOTA PROPERTY MANAGEMENT (561-889-2308)
Listing Agent: Benjamin Schwab (561-889-2308)
8776 MIDNIGHT PASS RD #C107, SARASOTA, FL 34242
$3,500292 Days on yellowkey MLS ID: A4661654
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1338 Built: 1975Community: Island Reef ISpa: NoCondo
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)
460 BEACH RD #A1, SARASOTA, FL 34242
$8,0002047 Days on yellowkey MLS ID: A4481650
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1363 Built: 1980 Tax: $9,551 (2021)Community: SpindriftCondo
Taxes:$9,551
Tax Year: 2021
Remarks: Available May 2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the pristine sugary quartz sandy beach or take a swim in the turquoise waters of the Gulf. Just a short distance to shopping, dining and nightlife of Siesta Key Village.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Brenda Cozy (941-350-4889)
8770 MIDNIGHT PASS RD #302B, SARASOTA, FL 34242
$4,0001075 Days on yellowkey MLS ID: A4573996
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1975Community: Island Reef ICondo
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
$11,00016 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)
1355 S PORTOFINO DR #103, SARASOTA, FL 34242
$12,00017 Days on yellowkey MLS ID: A4693257
Bed: 2 Bath: 2.0 Gar: 1 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: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Teresa Ribaudo (941-376-4500)
357 TIERRA MAR LN #5, SARASOTA, FL 34242
$8,50019 Days on yellowkey MLS ID: A4693123
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2012 Built: 2006Community: Village PlaceTownhouse
Remarks: Located in the heart of Siesta Key, live the island lifestyle year-round in this stunning turnkey furnished townhome, tucked away in a quiet enclave of only six residences, offering the perfect blend of privacy, comfort, and convenience. Available now for annual lease. This immaculate and spacious townhome features 3 bedrooms, 2.5 baths, and tasteful coastal furnishings throughout. Upon entering, you are welcomed by gleaming hardwood floors, plantation shutters on all windows, and a bright open-concept floor plan designed for comfortable island living. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen, complete with granite countertops, wood cabinetry, gas range, stainless steel appliances, breakfast bar with bar stools, and a water filtration system. Upstairs, the tastefully furnished primary suite offers a king-size bed, private balcony, luxurious ensuite bath with a jetted soaking tub, separate walk-in shower, private water closet, and an oversized walk-in closet with built-in shelving. The second guest bedroom features a queen bed and charming Juliette balcony with a peek view of the canal and private dock, while the third bedroom offers two twin beds, ideal for guests or family. Relax with a morning coffee or evening book on the peaceful screened lanai overlooking the garden patio. Additional features include an attached two-car garage and access to the community’s private pool. Residents also enjoy the private dock located directly across the street — perfect for kayaking, paddleboarding, or fishing. Enjoy the ultimate island lifestyle just a short walk from the world-famous Siesta Key Beach, renowned for its crystal quartz sand and turquoise Gulf waters, as well as Siesta Key Village, where you’ll find charming boutiques, waterfront dining, entertainment, and nightlife. Beyond the island, Sarasota offers endless attractions including museums, festivals, golf, boating, sailing, jet skiing, sunset dinner cruises on Sarasota Bay, and convenient access to University Town Center shopping, Sarasota-Bradenton International Airport, and I-75.
Listing Agent: Chrissie Cummings (772-532-8229)
1257 TREE BAY LN, SARASOTA, FL 34242
$10,00019 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)
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