Location: Sarasota , 34239
Do Not Show Listings
1738 SIESTA DR, SARASOTA, FL 34239
$6,50038 Days on yellowkey MLS ID: A4692339
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2131 Built: 2013Community: GranadaSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year:
Middle School: Brookside Middle
Remarks: Available June 1st, this newer (2013) “West of Trail” pool home offers an ideal opportunity to get settled ahead of the upcoming school year in the highly regarded Southside Elementary district, just a short bike ride away. Offered at $6,500/month with an annual lease preferred (6-month considered), the home provides flexibility with furnishings — available furnished or unfurnished. Elevated 22 feet above sea level in an X flood zone, it delivers both peace of mind and easy coastal living with a thoughtful layout featuring 4 bedrooms along with a versatile downstairs bonus space ideal for a media room, playroom, or additional lounge area. All bedrooms located on the 2nd level with bonus room, great room and kitchen on the main. Southern exposure fills the coastal-casual great room and updated kitchen with natural light, overlooking a private saltwater pool and lush tropical setting. Pocketing sliders create seamless indoor-outdoor living, perfect for relaxing or entertaining beneath the flowering plumeria. Designed for low-maintenance living, the property includes artificial turf, mature landscaping, and multiple outdoor gathering areas, with pool care, lawn care, and internet included in the rent. A two-car garage features a Tesla Level 2 EV charger and space for bikes and beach gear. Located in the historic Granada neighborhood with easy access to Southside Village dining, including Shakespeare’s Craft Beer & Gastro Pub, and just 10 minutes to both Siesta Key and Downtown Sarasota. Pets considered on a case-by-case basis with owner approval and deposit.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ryan Adamson, Pa (941-713-9234)
3008 HILLVIEW ST, SARASOTA, FL 34239
$2,30084 Days on yellowkey MLS ID: A4686754
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $300 (11.5%) on 05/05/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1095 Built: 1953Community: Rio Vista ResubSingle Family
Elementary School: Alta Vista Elementary
Remarks: Available for an annual lease, this updated 3-bedroom, 2/1-bathroom cottage is tucked away on a quiet dead-end street in the heart of Sarasota. The open-concept living area features a unique tongue-and-groove ceiling and rustic wood beams, giving the home a warm, custom feel. You’ll find a modern kitchen with light color shaker cabinets, stone countertops, and stainless steel appliances, plus durable luxury vinyl flooring throughout. No carpet here. The primary suite includes a private, renovated bath with contemporary tile and a new vanity. Outside, the oversized backyard offers plenty of space and privacy. This unfurnished home is minutes from Sarasota Memorial Hospital, Downtown, and the world-class beaches of Siesta Key. Move-in ready and perfectly located for a convenient Sarasota lifestyle. CALL TODAY.. ***PLEASE NOTE THAT WATER IN THIS PROPERTY IS SUPPLIED BY A WELL AND SEPTIC SYSTEM-therefore you have NO water bill!.***
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Hamid Mohajir (941-557-8556)
2365 WALDEMERE ST, SARASOTA, FL 34239
$7,000375 Days on yellowkey MLS ID: A4654509
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2300 Built: 2023Community: Loma Linda ParkSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Long-term or short-term leases can start from SEPTEMBER 10, 2026 for $7000 OR **option**SEASONAL RATE from December 1, 2026 through April,2027 is $12,000. (**February-March 2027 rented**). Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our alternative property named "SunShine Sarasota" (2375 Waldemere St, Sarasota), located next to "Sky Blue Sarasota" (2365 Waldemere St). Experience unparalleled luxury in this breathtaking new construction Mid Century Modern Residence! Welcome to this newly constructed masterpiece in the highly sought-after Arlington Park neighborhood. This stunning 4-bedroom, 3-bathroom home encompasses over 2,300 sq. ft. of flawless living space, crafted for both practicality and memorable family gatherings. Immerse yourself in the pinnacle of upscale living in this newly built masterpiece, ideally positioned near Siesta Key and the lively core of Downtown Sarasota. This remarkable home presents a perfect fusion of sophistication and comfort, tailored for those who appreciate a luxurious yet cozy lifestyle. Enter your personal haven where a private, heated swimming pool creates a resort-style atmosphere that encourages relaxation and leisure. The beautifully crafted outdoor area offers picturesque settings for enjoying the warm Florida breezes. The interior of the home exemplifies refined living with an open-plan layout that facilitates a seamless transition between the living, dining, and kitchen spaces. The residence is embellished with opulent features, including tiles, fixtures, and contemporary cabinets, adding a hint of European elegance to the environment. Conveniently situated near the shops and dining options of Southside Village and just minutes away from the vibrant downtown area, Marina Jack, St. Armands Circle, and the famous Siesta and Lido beaches, this home provides both luxury and accessibility. The property boasts a stunning FULLY FENCED private backyard with a heated pool, surrounded by lush palm trees. ***Location location location*** Only 6 miles to the SIESTA KEY BEACH and 5 miles to LIDO KEY BEACH. Both beaches have large public parking lots and a concessions stand with good hot food and frozen drinks. Siesta Beach's sand is 99% quartz l which makes it white and powder soft. Siesta Key also has two lively areas for dining. The Siesta Key village has restaurants and a couple stores. Another area by the South bridge has several restaurants. Grab your FISHING pole and head to the water, just 1.3 miles to the Siesta Dr - north bridge for fishing. DOWNTOWN is 2 1/2 miles away with restaurants, arts, shopping, Whole Foods and farmers market. Downtown has too many restaurants to name such as: Marina Jack’s, O’Leary Tiki Bar and grill, Owen’s Fish Camp, Mediterraneo. You can also take sightseeing boat cruises. LIDO KEY is just a couple miles from downtown. It is an exciting spot with lots to do including kayaking/stand up paddle boarding in the mangroves, hang out at Lido Beach or stroll around the restaurants and stores of St Armands Circle. AIRPORTs: Sarasota-Bradenton International Airport-SRQ (7 miles), Punta Gorda Airport- PDG: (50mi) Clearwater Airport (PIE): (57 mi) Tampa Airport (TPA): (60m)
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Claudia Dybala (773-318-5796)
2375 WALDEMERE ST, SARASOTA, FL 34239
$7,000375 Days on yellowkey MLS ID: A4654505
Remarks: Please contact the Listing Agent to obtain details about the WEEKLY and MONTHLY rates. Available Dates in 2026: Short Term or Long-term starting from AUGUST 1, 2026 for $7000 OR **option**SEASONAL RATE from December 2026 through April, 2027 is $12,000. (February-March 2027 is already booked). Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our alternative property named "Sky Blue Sarasota" (2365 Waldemere St, Sarasota), located next to "SunShine Sarasota" (2375 Waldemere St). Experience unparalleled luxury in this breathtaking new construction Mid Century Modern Residence! Welcome to this newly constructed masterpiece in the highly sought-after Arlington Park neighborhood. This stunning 4-bedroom, 3-bathroom home encompasses over 2,300 sq. ft. of flawless living space, crafted for both practicality and memorable family gatherings. Immerse yourself in the pinnacle of upscale living in this newly built masterpiece, ideally positioned near Siesta Key and the lively core of Downtown Sarasota. This remarkable home presents a perfect fusion of sophistication and comfort, tailored for those who appreciate a luxurious yet cozy lifestyle. Enter your personal haven where a private, heated swimming pool creates a resort-style atmosphere that encourages relaxation and leisure. The beautifully crafted outdoor area offers picturesque settings for enjoying the warm Florida breezes. The interior of the home exemplifies refined living with an open-plan layout that facilitates a seamless transition between the living, dining, and kitchen spaces. The residence is embellished with opulent features, including tiles, fixtures, and contemporary cabinets, adding a hint of European elegance to the environment. Conveniently situated near the shops and dining options of Southside Village and just minutes away from the vibrant downtown area, Marina Jack, St. Armands Circle, and the famous Siesta and Lido beaches, this home provides both luxury and accessibility. The property boasts a stunning FULLY FENCED private backyard with a heated pool, surrounded by lush palm trees. ***Location location location*** Only 6 miles to the SIESTA KEY BEACH and 5 miles to LIDO KEY BEACH. Both beaches have large public parking lots and a concessions stand with good hot food and frozen drinks. Siesta Beach's sand is 99% quartz l which makes it white and powder soft. Siesta Key also has two lively areas for dining. The Siesta Key village has restaurants and a couple stores. Another area by the South bridge has several restaurants. Grab your FISHING pole and head to the water, just 1.3 miles to the Siesta Dr - north bridge for fishing. DOWNTOWN is 2 1/2 miles away with restaurants, arts, shopping, Whole Foods and farmers market. Downtown has too many restaurants to name such as: Marina Jack’s, O’Leary Tiki Bar and grill, Owen’s Fish Camp, Mediterraneo. You can also take sightseeing boat cruises. LIDO KEY is just a couple miles from downtown. It is an exciting spot with lots to do including kayaking/stand up paddle boarding in the mangroves, hang out at Lido Beach or stroll around the restaurants and stores of St Armands Circle. AIRPORTs: Sarasota-Bradenton International Airport-SRQ (7 miles), Punta Gorda Airport- PDG: (50mi) Clearwater Airport (PIE): (57 mi) Tampa Airport (TPA): (60m)
1537 SIESTA DR, SARASOTA, FL 34239
$18,50036 Days on yellowkey MLS ID: A4692741
REDUCED by $1,500 (7.5%) on 05/29/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3727 Built: 2023Community: Sunset Bay SubSingle Family
Remarks: Welcome to Siesta by the Bay! This turnkey luxury home features 4 ensuite bedrooms, water views of the bay, pool bath and half bath, outdoor shower, outdoor kitchen, heated pool, putting green, and 3 car garage. Enjoy a private backyard with an expansive outdoor dining area and bar with multiple areas to exercise and lounge. Located near the Siesta Key North bridge, you’re minutes from world famous beaches, downtown Sarasota, Hillview Shopping Plaza, Sarasota Memorial Hospital, fine dining, and many more popular activities that Sarasota has to offer. Home is available for short-, mid-, and long-term rental. Rates vary based on season.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Tina Ellis (512-550-1117)
2216 WEBBER ST #C, SARASOTA, FL 34239
$1,55047 Days on yellowkey MLS ID: A4688118
REDUCED by $50 (3.1%) on 05/28/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 650 Built: 1956Community: Long MeadowSingle Family
Remarks: Totally redone, 2 bedroom, 1 bath and a den house available. New kitchen, new paint, appliance, blinds etc. Back and side yard are fully fenced. Near Southside Elementary School, Southside Village shops and restaurants. A quick walking path to Westfield Siesta Key mall and Shops at Siesta Row. Near Sarasota Memorial Hospital and about 2-3 miles from downtown Sarasota.
Listing is courtesy of: MARLENE LANCASTER REALTY (941-374-7700)
Listing Agent: Sarah Massey, Pa (941-374-2525)
3001 BEE RIDGE RD #124, SARASOTA, FL 34239
$1,20028 Days on yellowkey MLS ID: A4693660
0 Days Off yellowkey (back on 5/28/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 560 Built: 1964Community: South GateSpa: NoApartment
Elementary School: Wilkinson Elementary
Remarks: One or more photo(s) has been virtually staged. Move-in Specials: Only $700 Security Deposit! Apply before June 1st and get half off your Application Fee. This first floor, 1BR, 1BA end unit is just what you've been looking for! The kitchen is adorned with bright, hardwood cabinets and includes a refrigerator, range, and microwave for all your cooking needs. The open living and dining area offers plenty of space to host friends and family and stays brightly illuminated by the sliding glass doors that lead onto the covered paved patio space. The bedroom down the hall, and a sizeable bathroom complete the remainder of this unit. Centrally located off Bee Ridge, you will be minutes away from shopping, restaurants, and entertainment, and just a short drive to one of the best beaches in the country! Ridge Garden offers residents assigned parking, a sparkling community pool, on-site laundry, a sun deck, community grills, and a dog park. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative to qualified renters! ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee Pets: Pet(s) considered, up to 35 lbs. $250 Non-refundable pet fee. Included: Trash service, lawn care, and pest control THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)
Listing Agent: Mj Loparco (941-216-0022)
1865 ORCHID ST, SARASOTA, FL 34239
$7,500769 Days on yellowkey MLS ID: A4609514
REDUCED by $500 (6.3%) on 05/28/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2252 Built: 1953Community: Poinsettia Park 2Single Family
Remarks: Welcome to tropical paradise! This stunning home away from home offers the perfect blend of relaxation and fun for all. Take a dip in the brand-new saltwater pool and spa, wind down by the cozy firepit. With spacious bedrooms, a fully equipped kitchen, and cozy living areas, you'll have everything you need! Distance from Siesta Key Beach: 4.5 miles Distance from downtown Sarasota: 2.7 miles Distance from St. Armand Circle and Lido Key: 5.4 miles This beautiful 4-bedroom, 3-bathroom turnkey furnished property offers a spacious and open concept layout. The open kitchen seamlessly flows into the dining space and living room, creating the perfect space for entertaining and spending quality time with family and friends. One of the highlights of this property is the stunning pool and spa, where you can enjoy tropical drinks and unwind after a long day. Surrounding the pool are comfortable sun loungers, where you can relax and soak up the sun. There’s plenty of room for the whole family! Available for short/mid- and long-term rental.
Listing is courtesy of: COMPASS FLORIDA LLC (305-851-2820)
3425 FAIRVIEW DR, SARASOTA, FL 34239
$2,950120 Days on yellowkey MLS ID: A4682215
REDUCED by $50 (1.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 1965Community: South GateSingle Family
Remarks: ANNUAL FURNISHED 3 BEDROOM PLUS DEN POOL HOME AVAILABLE FOR ANNUAL LEASE IN SOUTH GATE! (Owner will consider unfurnishing the home.) The fully updated home has a beautiful kitchen with granite counters and stainless-steel appliances, modern bathrooms featuring matching granite, a walk-in closet in the primary bedroom, an open floor plan with a spacious great room adjacent to the kitchen, and a bright office overlooking the pool. The expansive covered outdoor area provides shade and an inviting spot for gatherings with friends and family, while the large, screened pool offers ample space for swimming laps or simply relaxing in the sun. The split floor plan ensures privacy, with the master suite separated from the guest bedrooms and office. The excellent location provides easy access to downtown Sarasota, shopping, dining, Siesta Key Beach, Lido Key, and the Legacy Trail. Lawn and pool maintenance included.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Alex Lane (941-960-3080)
1850 WEBBER ST, SARASOTA, FL 34239
$15,00026 Days on yellowkey MLS ID: A4693021
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026Community: Poinsettia Park 2Spa: YesSingle Family
Remarks: One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Dyrk Dahl (941-320-7373)
1773 HARMONY LN, SARASOTA, FL 34239
$5,00023 Days on yellowkey MLS ID: A4692810
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1098 Built: 1953Community: Bay View Heights AddSingle Family
Remarks: OFF SEASON RENTAL ONLY! This west of Trail, west of Osprey home rests on the edge of Cherokee Park on a canopied street in one of the most sought-after locations in all of Sarasota—situated between the North Bridge to Siesta Key and downtown. Fully turnkey furnished and well-appointed, this is a charming two bed/two bath home perfect for experiencing the laid back Florida lifestyle. Walk to Morton's Market in Southside Village, Southside Elementary, Selby Gardens, or Bayfront Park. Be perfectly close to the bay, while not in a flood zone. Rays of sunshine filter through the tree canopy and into the windows, illuminating a bright and open floor plan. The split floor plan features each bedroom with its own bath on separate sides of the home. Enjoy spending evenings on the back patio amidst mature landscaping and dining al frescoat the outdoor table with umbrella for shade in the fully fenced and private yard.This Sarasota rental is located in the best area of Sarasota. Take a stroll down the street to watch the sunset over the water or enjoy a bike ride and explore this magical neighborhood. OFF SEASON RENTAL ONLY. AVAILABLE JUNE THROUGH NOVEMBER.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Bridget Gennett (941-224-4315)
3835 ALMERIA AVE #C3, SARASOTA, FL 34239
$1,90023 Days on yellowkey MLS ID: A4694273
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 925 Built: 1970Community: Westchester ICondo
Remarks: Near the north Siesta Key Bridge and bay. Amazing location. Walk to see sunset over Sarasota Bay. Unfurnished. 1 car covered parking. Minutes to Siesta Key Beach. Minutes to Hillview and Southside. Part of Southside Elementary school district. Dead end street. Walk to restaurants and shopping. top floor of a 2 story building with a big relaxing Lanai Covered Parking. In unit laundry Quiet location.
Listing is courtesy of: SUNCOAST LUXURY PROPERTIES (941-504-5348)
Listing Agent: Richard Dear (941-504-5348)
1726 FLOYD ST, SARASOTA, FL 34239
$8,000274 Days on yellowkey MLS ID: A4664721
Bed: 3 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1461 Built: 1954Community: Midwood ManorSingle Family
Remarks: SEASONAL RENTAL - Available June 1, 2026 -3/BR; 1.5/baths Renovated, beautifully designer-decorated modern home located in one of Sarasota's most coveted West of Trail locations - adjacent to stunning Harbor Acres! THE SPACE: This stylish, fully furnished home features three bedrooms (King, Queen, Queen), 1.5 baths, a one-car garage, a spacious, light-filled sunroom and a cozy reading nook. The home has all-new furnishings and is fully turnkey equipped to ensure a comfortable and enjoyable stay. Guests will also enjoy indoor-outdoor living with a charming front porch, al fresco dining on the beautiful back deck, and a large, well-maintained yard ideal for outdoor relaxation and entertaining. PRIME LOCATION: Located in the heart of Hudson Bayou, where you can enjoy the best of Sarasota at your doorstep! Walk to Sarasota Memorial Hospital, Marie Selby Botanical Gardens and the lively Southside Village, home to some of the city's top restaurants, bars, cafés, and shops. You're also just minutes away from Downtown Sarasota, world-famous Siesta Key Beach, Lido Key Beach, St. Armands Circle, and A-rated Southside Elementary School. PLEASE NOTE: No smoking/vaping of any kind anywhere on the property. Seasonal Rental Rates: Dec-Apr $9,000 (3 month minimum for rentals Dec - April); May-June $8,000; July-Aug $6,500, Sept-Nov - $8,000.
Listing Agent: Beth Harris (941-321-7148)
2916 WOODCREST DR, SARASOTA, FL 34239
$2,60044 Days on yellowkey MLS ID: A4691711
REDUCED by $200 (7.1%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1576 Built: 1963Community: South GateSingle Family
Remarks: Single lever FURNISHED 3 bed/2 bath house in Sarasota, Florida, in VERY SAFE NEIGHBOURHOOD. Just 3 miles from famous Siesta Bridge : white sand, friendly waves . Kitchen with granite counter top, equipped with everything you need. Laundry room, garage. Primary bedroom with bathroom attached, kids room with bunk bed. Third bedroom is on the other side, you will love to fall asleep while watching jumping bunnies in the backyard through a low window.
Listing is courtesy of: NEO REMARKETING (305-363-5091)
Listing Agent: Sam Razavi Razavi (305-570-2939)
1792 FLOYD ST, SARASOTA, FL 34239
$6,00027 Days on yellowkey MLS ID: A4693825
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2015 Built: 1951Community: Hudson BayouSpa: YesSingle Family
Remarks: Wonderful pool home in PRIME WEST OF TRAIL location, just a few blocks to Southside Village popular shops and restaurants and 1 block to Sarasota Memorial Hospital. The home was remodeled in 1996 and 2000 with vaulted ceilings, newer bathrooms and kitchen, split bedroom floor plan, pool, interior laundry room, tile or wood floors throughout and 1 car garage. Very limited rental availability in this sought after area. Primary bedroom has king sized automated bed, guest bedrooms have a king and a queen. Can be furnished or unfurnished, living areas are currently staged but furnishings will be brought in if desired. Open to different rental tenures but minimum of one month, prefer 6 month but open to annual also.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
2559 ARLINGTON ST, SARASOTA, FL 34239
$2,30049 Days on yellowkey MLS ID: A4690955
REDUCED by $200 (8.0%) on 05/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1266 Built: 1953Community: Turners J C SubSingle Family
Remarks: Discover this inviting 3-bedroom, 2-bathroom cottage nestled on a peaceful dead-end road in the heart of Arlington Park, one of Sarasota’s most sought-after neighborhoods. Just down the street from beautiful Arlington Park & Aquatic Complex, Sarasota Memorial Hospital and minutes away from Downtown Sarasota. Some thoughtful updates include granite countertops, stainless steel appliances, travertine tile, and impact windows. Call for terms and a private showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Wade Ongstad (941-705-0537)
2624 SUNNYBROOK DR, SARASOTA, FL 34239
$2,20066 Days on yellowkey MLS ID: A4688921
REDUCED by $200 (8.3%) on 05/15/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1480 Built: 1957Community: South GateSingle Family
Remarks: Located on a quiet meandering street in the centrally located community of South Gate, this 2 bedroom 2 bath 2 car garage home is available for rent immediately. The open floor plan home features a newly renovated kitchen with new cabinets, countertops, and stainless steel appliances. You will find easy care vinyl flooring throughout the home and both bathrooms are on point with new ceramic tile and vanity cabinets. The location is perfect, just minutes to Sarasota Memorial Hospital, beautiful Arlington Park and Aquatic Center, and neighborhood eateries and grocery stores. Enjoy the Florida lifestyle, call for more information today.
2441 WEBBER ST, SARASOTA, FL 34239
$9,50090 Days on yellowkey MLS ID: S5145822
INCREASED by $550 (6.1%) on 05/09/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2726 Built: 2025Community: Orange ParkSpa: YesSingle Family
Remarks: One or more photo(s) has been virtually staged. Brand-new 2025 contemporary pool home in Sarasota offering modern design, quality construction, and convenient access to the area’s best amenities. Located just minutes from downtown Sarasota, Siesta Key Beach, shopping, dining, and cultural attractions, this home delivers the ideal combination of style and location. Furnished or Unfurnished. Can be rented for seasonal rental price is subject to change based on season and availability. Situated on a private 85’ x 117’ fenced and professionally landscaped lot, the backyard features a heated pool and spa with sun shelf, creating a relaxing outdoor retreat perfect for entertaining or enjoying Florida living year-round. Built with all-concrete block construction, impact-rated windows and doors, and energy-efficient systems, the home offers durability, safety, and lower insurance costs. Inside, the open-concept design features 10+ foot ceilings, large windows, and abundant natural light. The gourmet kitchen includes a waterfall island, Monogram appliances, induction cooktop, InstaHot water, and custom cabinetry, and opens seamlessly to the main living and dining areas. The 2,726 sq ft single-story floor plan includes 4 bedrooms and 3.5 bathrooms, with three ensuite bedrooms providing privacy for guests or family. The primary suite offers dual walk-in closets and a spa-inspired bathroom with soaking tub and glass-enclosed shower. Located in the highly regarded Southside Elementary School district, this newly built home is move-in ready and ideally positioned in one of Sarasota’s most desirable neighborhoods.
Listing is courtesy of: GRAND STATE REALTY (305-781-9202)
Listing Agent: Oleksandr Blekherov (305-781-9202)
3700 S OSPREY AVE #216, SARASOTA, FL 34239
$1,80036 Days on yellowkey MLS ID: A4692764
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1979Community: Plaza GardensCondo
Remarks: WEST OF THE TRAIL...this charming 2nd floor condo offers 2 bedrooms and 1 bathroom. The balcony is enclosed with screens and windows. Excellent location, convenience is key with this property. Situated just around the corner from the north bridge and minutes away from the world renowned SIESTA KEY BEACH. Live the best of both worlds in a peaceful, quiet area and easy access to coastal living. This condo is conveniently located across the street from Publix, CVS, Cinebistro, restaurants and a post office. Properties like this don't come along very often. Call now for a showing before you miss out on this opportunity!
Listing Agent: Teresa Ribaudo (941-376-4500)
2327 HILLVIEW ST, SARASOTA, FL 34239
$25,000631 Days on yellowkey MLS ID: A4623881
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 3500 Built: 2024Community: Battle & TurnerSingle Family
Remarks: **SEASONAL / WEEKLY RENT PLEASE INQUIRE** Welcome to Tamiami Vise, a luxurious haven where comfort and style intertwine for a truly memorable getaway. This stunning retreat features a private heated pool, perfect for relaxing dips under the Florida sun. 6 bedrooms and 7 bathrooms. Step inside to discover a spacious living area, thoughtfully designed for relaxation after a day of exploring Siesta Key. The well-equipped kitchen offers everything you need to whip up delicious meals, including a Keurig coffee maker, dishwasher, and essential kitchen amenities.Outside, the second-level balcony and poolside dining area provide ideal spots to soak up the sunshine and enjoy al fresco dining. Beach towels, chairs, a cooler, and a caddy are available for your beach adventures. Stay entertained with 7 HD Smart TVs throughout the property. Tamiami Vise is conveniently located just a short drive from Siesta Key Beach, famous for its powdery white sand and crystal-clear waters. Explore the vibrant shops and restaurants nearby or simply unwind by the pool and bask in the Florida sunshine.
Listing is courtesy of: KELLER WILLIAMS CLASSIC GROUP (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
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