Location: Sarasota, 34242
Do Not Show Listings
5855 MIDNIGHT PASS RD #426, SARASOTA, FL 34242
$5,000937 Days on yellowkey MLS ID: A4581930
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1976Community: Harbor Towers Y & RCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
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!
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
131 WHISPERING SANDS CIR #V33, SARASOTA, FL 34242
$4,7508 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)
301 AVENIDA MADERA #B, SARASOTA, FL 34242
$12,600343 Days on yellowkey MLS ID: A4649548
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1970Single Family
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel appliances, fully supplied kitchen and a Keurig machine add to the feel of this house. Master suite with full bath, large family dining room looking over the canal. Enjoy grilling out, playing a game of corn hole or fish on the canal. Don't forget your fur babies either. This home is extremely pet friendly. NOTE: The pool area is a shared space with our other location - Unit A (VRBO# 1077749). Need more rooms? The Units are attached, but have separate private entrances. There are no shared walls to any rooms of the Units. For guest safety, there are outside monitored security cameras. Unit is smoke free. No smoking is permitted inside the units. Enjoy your stay!! :-) Renters assume all risks associated with entering the property and understanding that Broker accepts no liability, including for COVID-19, Renter notes to hold Broker harmless and release Broker from any and all liability, including COVID-19. Rates Change through the Calendar Year.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
5310 HIDDEN HARBOR RD, SARASOTA, FL 34242
$6,00043 Days on yellowkey MLS ID: A4682592
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2295 Built: 1977Single Family
Remarks: Siesta Key Annual rental. Located just a half mile from Siesta Key Beach, this four-bedroom, two-bath home is tucked away in the quiet Hidden Harbor area. Set in a beautiful tropical environment with canopy-lined streets, the property features 2,300 square feet of living space and a 1200-square-foot lanai. The interior offers an open floor plan with vaulted ceilings, skylights, and updated kitchen and baths. Each bedroom includes a private balcony with shelving in each closet. The master bathroom features a soaking tub, shower, and a double vanity with marble counters. Sliding doors from the living room and kitchen/family room open to a large screened-in lanai and a two-story deck. Outside, you will find a pristine, caged, heated swimming pool with waterfall and spa - perfect for entertaining. The home is situated on an oversized lot with a gated entrance. It offers two zone air-conditioning and heating units. The home has a metal roof and hurricane impact windows and has a 2-car detached garage. Enjoy the island life with proximity to the Gulf of Mexico and the boutiques, restaurants, and nightlife of Siesta Key Village. Rent includes weed control, leaf pickup, pool maintenance, pest control, and internet. The fireplace is not for tenant use.
Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)
Listing Agent: Margaret Young (941-359-3435)
1203 LYRIC LN, SARASOTA, FL 34242
$10,000280 Days on yellowkey MLS ID: A4656825
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1626 Built: 1964Community: Acreage & UnrecSingle Family
Remarks: One or more photo(s) has been virtually staged. Coastal Luxury Rental – Steps from Siesta Key Beach ***Seasonal or Annual Lease Available | 2 Bed • 2 Bath • Detached Garage /Game room/Workspace • RV Pad w/ 50-Amp + Pump-Out. Live the ultimate Siesta Key lifestyle in this completely remodeled and newly furnished coastal retreat, ideally located just ½ mile from the #1 rated Siesta Key Beach.***This stunning 2-bedroom, 2-bath residence features a private detached garage that doubles as a game room, home office, or creative workspace, plus a dedicated RV pad with 50-amp electrical hookup and pump-out station — an extremely rare amenity this close to the beach. ** Property Highlights: **Fully renovated interior – like new **Professionally furnished – turnkey & move-in ready** Bright open floor plan with coastal-inspired design** Modern kitchen with updated appliances & finishes ** Detached garage / game room / workspace – rare bonus feature ** Private outdoor areas perfect for relaxing or entertaining. ** Prime Location:** ½ mile to Siesta Key Beach ** Minutes to Siesta Village restaurants, nightlife & boutiques ** Easy access to downtown Sarasota, marinas, boating & golf.***Lease Options: Fully Furnished > Seasonal or Annual lease available*** This is a rare opportunity to lease a fully remodeled, professionally furnished home with RV parking & hookups, located minutes from Siesta Key Beach — perfect for snowbirds, traveling executives, digital nomads, boaters, and RV enthusiasts. PICTURES ARE REPRESENTATION ONLY. FURNISHING IN PROGRESS. Picture will be updated weekly
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
7006 MIDNIGHT PASS RD, SARASOTA, FL 34242
$1,70041 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)
7006 MIDNIGHT PASS RD #2, SARASOTA, FL 34242
$1,80041 Days on yellowkey MLS ID: A4683272
Remarks: Welcome to your refreshed beach retreat on Siesta Key at 7006 Midnight Pass Rd #2. This bright and inviting 1-bedroom, 1-bath residence offers approximately 850 square feet of easy, coastal living with new paint throughout and a brand-new kitchen featuring granite countertops and stainless appliances (dishwasher and microwave included). 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, and the updated bath includes a step-in shower plus new cabinetry and a granite vanity. 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
7006 MIDNIGHT PASS #1 RD, SARASOTA, FL 34242
$1,80041 Days on yellowkey MLS ID: A4683259
Remarks: Welcome to your renovated beach retreat on Siesta Key at 7006 Midnight Pass Rd. This bright and inviting 1-bedroom, 1-bath residence offers approximately 850 square feet of easy, coastal living with new paint throughout and a brand-new kitchen featuring granite countertops and stainless appliances (dishwasher and microwave included). 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, and the updated bath includes a step-in shower plus new cabinetry and a granite vanity. 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
4822 OCEAN BLVD #5E, SARASOTA, FL 34242
$2,2957 Days on yellowkey MLS ID: A4687601
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 820 Built: 1973Community: Siesta TowersCondo
Remarks: Beautifully updated waterfront turnkey furnished 1-bedroom condo with breathtaking views of the Gulf of Mexico and Downtown Sarasota, all just a short stroll from the shops, restaurants, and nightlife of Siesta Key Village. RENT NOW WITH ZERO DEPOSIT MOVE IN! Available on a 6 or 12-month lease, this condo is turn-key - just bring your clothes and toothbrush! Rent includes Water, Cable TV and Internet! Very nicely furnished and available for immediate occupancy. Enjoy morning coffee or sunset cocktails from your private screened lanai overlooking the water. Inside, you'll find spacious living, a walk-in closet, and ample storage, plus two large LED TVs, smart lighting, and stylish furnishings throughout. Brand New High Impact Glass Sliders. This property offers unmatched amenities: a heated waterfront pool, cocktail dock, fishing pier, fitness center, library, club room with full kitchen, secure bike room, outdoor gas grill, assigned resident and guest parking, and additional storage. The recently renovated lobby adds to the upscale coastal lifestyle. PETS ALLOWED. Available for immediate occupancy. Rent with Zero Deposit.
Listing is courtesy of: SECURE DOOR PROPERTY MANAGEMENT (941-231-4065)
Listing Agent: Andrew Clark (941-929-4223)
6006 MIDNIGHT PASS RD #15, SARASOTA, FL 34242
$7,500380 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!!
5354 SHADOW LAWN DR, SARASOTA, FL 34242
$4,75022 Days on yellowkey MLS ID: A4685655
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2083 Built: 1964Community: Siesta IslesSingle Family
Remarks: Available on an Annual Lease. This is a nicely furnished 3 bedroom 2 bath Grand Canal pool home with a deep-water dock on Siesta Key! The home has a foyer entry with etched glass front doors. The open concept floor plan includes living, dining and family rooms which feature pocketing sliding glass doors leading to the large, screened-in lanai, paver deck and sparkling free-form pool overlooking the waterway. The remodeled kitchen features an oversized island with seating for six, wood cabinets, granite countertops, a five-burner gas cooktop, stainless steel appliances and abundant storage. The waterfront master-bedroom features direct access to the pool and has views of the Grand Canal. The master bathroom has a walk-in closet and private toilet / shower room with a tub/shower combination. There are two additional bedrooms and a full bath. The laundry room has additional storage and is located near the kitchen and two car garage. The screened in patio has a pool and view of the canal. The zero-scaped yard is maintenance free. You are able to fish, kayak, paddleboard or boat from the dock in your own backyard. Located in the waterfront community of Siesta Isles, near the powdery white sands of world-famous Siesta Beach and near Siesta Village's charming shops and restaurants. Amenities include, lawn care and pool care. There is a propane tank for the gas stove that is full, however the tenant is responsible to refill it when depleted and at the end of the tenancy. We score every application. If an application doesn’t score high enough, the resident may be required to place the equivalent of two months’ rent in a security deposit. Please be aware that leasing this property includes a non-optional Home Assistant Services Package that will cost an additional $39 per month. These services and their cost are separate from Tenant’s monthly rent payment and all other payments described in the Lease or any separate Lease addendums. The Home Assistant Services offered are described in the Resident Welcome Packet which can be viewed on our website at Sarasota Management & Leasing.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING (941-377-8400)
Listing Agent: Todd Roughton (941-377-8400)
6480 MIDNIGHT PASS RD #506, SARASOTA, FL 34242
$12,000382 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
$3,400119 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
$5,00041 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
$6,55013 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
$3,35031 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
$12,0001125 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)
4879 COMMONWEALTH DR, SARASOTA, FL 34242
$15,000271 Days on yellowkey MLS ID: A4657954
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2450 Built: 1957Community: Siesta BeachSingle Family
Remarks: FULLY FURNISHED rental available in Siesta Key, close to the beach and walking distance to Siesta Key Village. RENTAL PRICE depends on total LENGTH OF STAY. Rent a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Boasting 2,500 square feet of light-filled living space, this 4-bedroom, 3-bathroom residence has been meticulously renovated while preserving its original architectural integrity. Clean lines, expansive impact windows, and an open floor plan define the home’s iconic style, inviting the outdoors in and creating a sense of calm sophistication throughout. Inside, the split floor plan provides distinct zones for privacy and connection. The primary suite is a sanctuary of its own, complete with private access to the outdoors, a luxurious bath featuring a freestanding soaking tub, and a marble-lined walk-in shower. On the opposite side of the home, three additional guest bedrooms provide comfort and style—including a junior suite with its own private bath, full marble detailing, and oversized picture window with views of the pool and deck area. High-end renovations include: New commercial-grade roof (30-year lifespan); High-impact windows and doors throughout the home; Durable wood-grain tile flooring; Quartz waterfall countertops & custom wood cabinetry in the kitchen; Floor to ceiling marble tile in all bathrooms; All new major appliances including HVAC, pool equipment and water heater; Spray foam insulation throughout the home for an extra layer of protection; and designer finishes and curated lighting throughout. Step outside to your personal paradise: a heated saltwater pool with screened enclosure, surrounded by lush tropical foliage for complete privacy and serenity. The home is ideally located just blocks from Roberts Bay and less than a mile from the award-winning crystal sands of Siesta Key Beach. A true retreat, the lushly landscaped double lot offers unmatched privacy and space—perfect for entertaining or simply relaxing beneath the tropical canopy. Whether you're a collector of architectural homes, a beach lover, or simply someone looking for the rare blend of heritage, location, and luxury, this one-of-a-kind property is your opportunity to own an iconic piece of Sarasota’s rich design legacy.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Daniel Petrilla (610-772-5881)
9397 MIDNIGHT PASS RD #501, SARASOTA, FL 34242
$5,000109 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)
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