Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3411 CLARK RD #112, SARASOTA, FL 34231
$1,90093 Days on yellowkey MLS ID: A4689174
REDUCED by $50 (2.6%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974Community: SiennaSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year:
Middle School: Brookside Middle
Remarks: Fully remodeled 2-bedroom, 2-bath condo in Sienna Park just minutes from Siesta Key Beach! This move-in ready unit features brand new appliances and a never-used washer and dryer, a bright open layout, and a private patio perfect for enjoying Florida living year-round. Enjoy resort-style amenities including a pool, tennis courts, fitness center, sand volleyball court, dog park, and BBQ areas. Ideally located near shopping, dining, and entertainment, this pet-friendly community offers the best of Sarasota convenience and coastal lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Jordan Cadavid Jones (941-900-5968)
3217 RESTFUL LN, SARASOTA, FL 34231
$2,99526 Days on yellowkey MLS ID: A4697554
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 891 Built: 1977Community: Restful PinesSpa: NoSingle Family
Remarks: Looking for a place to spend the season, explore Sarasota before making a purchase, or need a comfortable home while yours is being built or renovated? This fully furnished home offers a flexible, turnkey solution in one of Sarasota's most convenient locations. The home features a private pool, fenced backyard, and thoughtfully designed living spaces that make it easy to settle in for an extended stay. Tastefully furnished and fully equipped, everything is ready for you to enjoy from day one. Located just approximately 600 yards from Red Bug Slough County Park, you'll have easy access to walking trails, scenic ponds, picnic areas, and a playground. Siesta Key Beach is only about two miles away, with shopping, dining, golf, and everyday conveniences nearby. Whether you're escaping colder weather, relocating to the Sarasota area, waiting for a new home to be completed, or simply want to experience the Sarasota lifestyle before buying, this home offers the comfort and flexibility to make the transition easy. Fully furnished. Private pool. Fenced yard. Six-month minimum lease. Available for seasonal or extended stays.
Listing is courtesy of: EDGE GROUP REAL ESTATE (941-914-4717)
Listing Agent: Tom Sannicandro (508-872-4747)
4336 CACTUS AVE, SARASOTA, FL 34231
$2,35026 Days on yellowkey MLS ID: A4697410
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1651 Built: 1985Spa: NoSingle Family
Elementary School: Wilkinson Elementary
Remarks: Perfectly situated in one of Sarasota’s most central neighborhoods, this charming two bedroom, two bath home is just minutes from Downtown Sarasota, Siesta Key, shopping, dining, and everyday conveniences. The home offers a comfortable layout with an open formal living and dining area, plus an oversized family room with a fireplace. The kitchen has a lot of charm, including a small eat-in area, greenhouse window, and great natural light. The attached garage also includes a workshop space, which is great for storage, projects, and more. Out back, the screened lanai offers a nice place to relax, with a gas grill already in place for added convenience. Being fully turnkey furnished, this home provides an incredibly easy move-in experience. Simply bring your clothes and settle right in. Furnished rentals of this quality and condition rarely last long. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Cole Collins (941-350-8360)
420 BEACH RD #502, SARASOTA, FL 34242
$6,50026 Days on yellowkey MLS ID: A4696888
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980Community: Siesta Gulf ViewCondo
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Remarks: Turnkey furnished beachfront retreat on Siesta Key, one-month minimum rental. Greet each morning to the sound of the Gulf and close every evening beneath a glowing horizon and dazzling sunset from this gulf-front residence at Siesta Gulf View. Two bedrooms and two baths, this home opens onto a 31-foot screened and glass-enclosed lanai that runs the full width of the unit, framing an uninterrupted western sweep of Siesta Beach and the Gulf. Step out from the living room, kitchen, or primary suite to take in both the coastline and the wild dune grasses below. The primary suite has a king size bed, walk in closet, and double vanity. The second bedroom has queen size bed and private bath. Kitchen has a built in desk. Beautifully updated and meticulously maintained, equipped with all the comforts of home. Take the stairs or elevator down for a quick run to the sand, pool, tennis/pickleball, gym, or garage. Siesta Gulf View is a gated, 59-unit enclave set across seven acres with 400 feet of frontage on the famed quartz sands. Enjoy a 25'x40' heated pool, tennis and pickleball courts, a refreshed fitness studio, and a clubhouse. A private gate leads to a boardwalk with picnic spots, two grills, and benches made for birdwatching. Assigned under-building parking, generous guest spaces, ground-floor overflow storage. Best of all, the energy of Siesta Key Village, its dining, boutiques, and live music sits just a few blocks away. Island-style living, an unobstructed panorama, and a full-length beachfront lanai: a rare invitation to call this stretch of coast your own, whether its a month or the entire season, you won't want to leave!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Joanna Benante (941-356-7718)
3269 BENEVA RD #102, SARASOTA, FL 34232
$1,20088 Days on yellowkey MLS ID: A4690193
REDUCED by $800 (40.0%) on 06/02/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1979Community: Village Brooke Sec 3Condo
Remarks: Looking for a 6-month lease on a comfortable place to explore Sarasota without stretching your budget? Settle right in at this inviting first-floor condo in Village Brooke, a friendly, centrally located community that makes it easy to feel at home. Step inside to a well-designed kitchen with attractive counters and a handy pass-through bar top to the dining area, ceramic tile flowing through the main living spaces, and a generously sized bedroom with a walk-in closet. Out back, your private south-facing screened lanai is the spot you'll keep coming back to, shaded and breezy through the warmer summer months, with comfortable warmth as the season turns toward fall. Village Brooke sits just across from the Village Green public golf course and is known for its beautifully maintained grounds and genuinely welcoming atmosphere. There's always something going on: an active social calendar of weekly gatherings, seasonal events, and easy ways to get to know your neighbors. Residents enjoy two heated pools, tennis courts set up for pickleball too, shuffleboard, peaceful ponds with shaded gazebos, outdoor barbecue and picnic areas, and a clubhouse complete with billiards, a library, a gathering room, and a kitchen for social events. Best of all, daily living stays simple: water and sewer, basic cable, trash service, pest control, and grounds maintenance are all included. You're minutes from shopping, dining, and golf, and just a short drive to Sarasota's beaches and the Gulf waters of Siesta Key. For residents seeking comfort, community, and value through the summer and fall, this one checks every box, and a shorter lease term may be available with renegotiated rates. Property is also being offered for sale at $135,000. See MLS A4674580.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
1232 NORTHPORT DR, SARASOTA, FL 34242
$9,97528 Days on yellowkey MLS ID: TB8519681
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1794 Built: 1968Community: Royal Palm HarborSpa: NoSingle Family
Remarks: Annual Rental: Waterfront 3BD/2BA home with private pool and sailboat water with boat slip. Looking for a laid-back Siesta Key flip-flop lifestyle with urban conveniences? Discover 1232 Northport Drive, a secluded, peaceful setting less than one mile from world-famous Siesta Key beach. This updated island one-story home awaits your annual escape from daily demands, but not too far, as high-speed internet provides the AI connection between paradise and business. Bring your family, dog, and boat for an amazing year in the tropics. The home is currently furnished, and the owners will consider removing the furniture so you can move in your personal belongings for comfort. The home is offered as an annual rental that includes pool and grounds maintenance and inside laundry room with full sized washer/dryer; however, tenants are responsible for utilities, including renters’ insurance, water/sewer, and electricity. The application process includes a background check, with a desired minimum credit score of 680/person. No smoking, vaping, or recreational drugs permitted. The home is ready now for your arrival. Live your Siesta Key dream, waiting for your move. Call for private showings; in person or virtual.
Listing is courtesy of: BROCK REALTY INC. (941-313-1234)
Listing Agent: Lynn Brock (941-313-1234)
3201 BENEVA RD #201, SARASOTA, FL 34232
$1,7001114 Days on yellowkey MLS ID: A4574874
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 876 Built: 1978Condo
Remarks: GORGEOUS 2 BEDROOM, 2BATHROOM, TURNKEY FURNISHED SEASONAL RENTAL LOCATED IN THE HIGHLY SOUGHT-AFTER COMMUNITY OF VILLAGE BROOKE! This property is perfect for your Sarasota family vacation. When you walk into this unit you will love the light, bright and homie feeling you get. ALL OF THE FURNITURE IN THIS UNIT IS BRAND NEW! The large sliding glass door that leads out to your private screened in lanai lets in a ton of natural light. The kitchen is equipped with everything you will need during your stay for all of your cooking adventures. The master suite features a king size bed and tons of closet and draw space along with an updated master bathroom with a shower and tub combo. The spare bedroom is set up with two XL twin beds and desk for your working needs. Village Brooke features an array of amenities including two community pools, two tennis courts, pickleball, shuffleboard and a newly updated community club house that features a fully equipped kitchen, perfect for hosting private or community events. Laundry facilities are conveniently available in each building. Please call for your showing today. I am sorry no pets or trucks.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Kayla Lamb (941-315-9500)
2911 WOODPINE CT, SARASOTA, FL 34231
$4,30028 Days on yellowkey MLS ID: W7886784
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1275 Built: 1979Community: Woodpine LakeSpa: NoSingle Family
Remarks: Now Available for Rent! Located at 2911 Woodpine Ct in Sarasota, Florida**, this beautifully renovated 3-bedroom, 2-bathroom home offers the perfect balance of modern comfort, thoughtful design, and an unbeatable West of the Trail location. Tucked away on a quiet cul-de-sac within the highly regarded Riverview High School district, this move-in-ready home is just minutes from the sugar-white sands of Siesta Key Beach, Lido Beach, and the vibrant energy of downtown Sarasota. Inside, you'll find a bright and open floor plan that seamlessly connects the living, dining, and kitchen areas, creating an inviting space for both everyday living and entertaining. Large windows and sliding glass doors fill the home with natural light while showcasing peaceful views of the lush backyard. The updated kitchen features modern cabinetry, sleek countertops, and ample workspace. A desirable split-bedroom floor plan provides added privacy, with a spacious primary suite offering generous closet space and an updated en-suite bathroom. Two additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the screened-in porch and spacious backyard surrounded by mature landscaping, perfect for relaxing or entertaining. The attached two-car garage provides plenty of parking and additional storage. Enjoy an exceptional Sarasota lifestyle with easy access to Gulf Gate, Southside Village, St. Armands Circle, Selby Botanical Gardens, Marina Jack, Sarasota Bayfront, waterfront parks, boating, kayaking, shopping, dining, fitness studios, and Sarasota Memorial Hospital, all just minutes away. This exceptional rental offers the ideal combination of location, comfort, and convenience in one of Sarasota's most sought-after neighborhoods.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Maidelin Moreira Miranda (813-482-3920)
3755 S SCHOOL AVE #41, SARASOTA, FL 34239
$1,85081 Days on yellowkey MLS ID: A4691238
REDUCED by $200 (9.8%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972Community: Sunland AptsCondo
Elementary School: Southside Elementary
Remarks: VERY LOW MOVE-IN COSTS! ONLY FIRST MONTH'S RENT AND A $500 SECURITY DEPOSIT REQUIRED. LEASE OPTION WOULD BE CONSIDERED. FLEXIBLE LEASE TERMS AVAILABLE (GREATER THAN 6 MONTHS AND LESS THAN 12 MONTHS). Owner pays the association fees, and rent includes cable, water, sewer, trash, and more. Enjoy the convenience of Sarasota living in this beautifully updated 2-bedroom, 2-bath condominium located in a quiet and well-maintained 55+ community just minutes from world-famous Siesta Key Beach. Ideally situated only a few doors from the elevator, this move-in-ready residence offers both comfort and accessibility. Inside, you'll find a bright and inviting floor plan with abundant natural light, updated flooring, neutral finishes, and an open-concept living and dining area designed for easy everyday living. The kitchen features modern cabinetry, ample counter space, and a breakfast bar that opens to the main living area, making it ideal for entertaining or casual dining. The spacious primary suite includes a walk-in closet, en-suite bathroom, and private lanai access. The guest bedroom is thoughtfully positioned for privacy and offers generous closet space. Both bathrooms have been tastefully updated with clean, modern finishes. Relax and unwind on the private lanai while enjoying peaceful community views. Additional conveniences include elevator access, nearby storage, and laundry facilities. One of the property's standout features is its exceptional walkability. LA Fitness, Aldi, the post office, restaurants, shopping, public transportation, and other daily conveniences are all located nearby, making it easy to enjoy an active and independent lifestyle without relying heavily on a vehicle. Conveniently located near downtown Sarasota, Siesta Key Beach, healthcare facilities, shopping, dining, and entertainment. This is an excellent opportunity to enjoy affordable, low-maintenance living in one of Sarasota's most desirable locations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
1650 STICKNEY POINT RD #50-202, SARASOTA, FL 34231
$1,950235 Days on yellowkey MLS ID: A4672337
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1975Community: Castel Del MareCondo
Remarks: Available starting May 15, 2026) Escape to this bright and inviting condo in the highly sought-after Castel Del Mare, located just minutes from the world-famous Siesta Key Beach, ranked the #1 beach in the USA. From the moment you arrive, you’ll be welcomed by the light, airy décor and spacious living areas that make this condo feel like a true coastal retreat. Thoughtful touches, including a large walk-in closet, ensure a comfortable and organized stay, while the stylish and relaxed design makes it the perfect setting for a seasonal getaway. Residents of Castel Del Mare enjoy resort-style amenities, including two sparkling pools—one overlooking the Intracoastal Waterway—tennis courts, a fishing pier for casting a line or watching dolphins play, a recreation room, and on-site management for convenience and peace of mind. Nestled along the Intracoastal Waterway, this community offers a rare blend of tropical beachside living and relaxation, where every day feels like a vacation. Don’t miss this opportunity to enjoy your fall escape in paradise—your Florida getaway awaits!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
1359 HARBOR DR, SARASOTA, FL 34239
$13,000295 Days on yellowkey MLS ID: A4665856
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3223 Built: 1947Community: Harbor AcresSpa: NoSingle Family
Remarks: STUNNING UNFURNISHED SINGLE FAMILY HOME IN THE SOUGHT AFTER COMMUNITY OF HARBOR ACRES IS AVAILABLE TO RENT!!! This is the one you've been looking for! Renovated from top to bottom this home has all the bells and whistles with a contemporary design, spacious floor plan, two stories, split bedrooms and a private second floor primary bedroom. The kitchen is truly the heart of this home with two islands, stainless appliances, double ovens, drawer microwave, counter and cabinet space for all your needs, open dining room space, coffee bar and large floor to ceiling windows that look into the lanai and backyard/pool area. The first floor has a spacious living room, three bedrooms, one of which has a fireplace in it. There is a jack and jill bathroom between two of the bedrooms both with large closets. The second floor primary suite is a true owners retreat with a large bedroom with built in walk in closet, separate wall closet, private oversized balcony that looks over the backyard and pool, bonus bedroom or den/office with built in closets and a large primary bathroom with double sinks, walk in shower, water closet, soaking tub, linen closet and heated towel rack. The backyard is a beautiful oasis for enjoying with a heated pool, fenced yard and plenty of lush landscaping and green space. The home has a half bathroom, laundry room with utility sink, full sized washer and dryer and a two car garage. The owner will consider a dog with a $300 non refundable pet fee and $1,500 refundable deposit. The home is available immediately for an annual rental. Close to downtown Sarasota, Siesta Key, opera house, theaters, restaurants and much, much more! Call today as this will not last long.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: C. Alison Hunter (941-587-5667)
3533 BAHIA VISTA ST, SARASOTA, FL 34239
$1,19529 Days on yellowkey MLS ID: A4695703
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 850 Built: 1986Community: HomecroftHalf Duplex
Elementary School: Alta Vista Elementary
Remarks: This comfortable 1 bed, 1 bath apartment in a 2-unit duplex offers affordable living in a great location. You’ll enjoy all major kitchen appliances (refrigerator, stove/oven, dishwasher, microwave) plus a washer & dryer in the unit. The neighborhood is known for its unique Amish/Mennonite heritage and local dining spots. First, last, and security required. Utilities not included. Sorry, no pets. First, last, and security deposit required.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Timothy Bloch (941-504-1111)
5440 RIVERBLUFF CIR #87, SARASOTA, FL 34231
$1,85048 Days on yellowkey MLS ID: A4695048
REDUCED by $100 (5.1%) on 06/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 864 Built: 1971Community: Strathmore Riverside ISpa: NoVilla
Remarks: Fully renovated and move-in ready, this charming 1-bedroom, 1-bathroom standalone villa is available for long-term rental or a minimum 3-month stay in the highly sought-after 55+ Strathmore Riverside Villas community. Available furnished or unfurnished to suit your needs — whether you are a snowbird looking for your perfect seasonal escape or seeking a peaceful year-round residence, this turnkey villa is ready for you. Fresh 2025 upgrades include a brand new kitchen with modern finishes, new flooring throughout, and new plumbing — simply move in and start living. The bright open-concept layout offers comfortable and easy living for up to 2 occupants, with an in-unit washer and dryer, covered carport, and attached storage room. The community is the star of the show. Start your morning with a swim in the large heated pool maintained at a year-round 85 degrees, spend your afternoon on the fishing dock, or stroll along the scenic Phillippi Creek waterfront. Additional amenities include a clubhouse, fitness room, shuffleboard courts, billiards, library, and two saunas. Conveniently located near Publix, Detwiler's Farm Market, Sarasota Memorial Hospital, Phillippi Farmhouse Market, and just minutes to world-famous Siesta Key Beach. Maximum occupancy 2 persons. Minimum lease 3 months, community rules. At least one occupant must be 55 or older. Association approval required prior to move-in.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Evona Poplawski (941-228-9455)
8625 MIDNIGHT PASS RD #506B, SARASOTA, FL 34242
$2,750135 Days on yellowkey MLS ID: A4684215
REDUCED by $600 (17.9%) on 05/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1222 Built: 1970Community: Bay Tree ClubCondo
Remarks: Available May 15 through October 31, 2026, at a newly reduced rate of just $2,300 per month! November and December are available for $2,750 per month, and January is available for $5,000. Also available as an annual rental for $3,350 per month. Enjoy private access to the soft white sands and tranquil beauty of Turtle Beach on Siesta Key from this beautifully furnished 5th-floor penthouse. Offering picturesque bay and treetop views, this move-in-ready residence is located within one of South Siesta Key's most desirable Gulf-to-Bay communities. Designed for effortless coastal living, the light-filled interior features an open split-bedroom floor plan and tile flooring throughout. The updated kitchen showcases granite countertops, additional cabinetry, and ample workspace, while both bathrooms have been refreshed with stylish new vanities. Take in sweeping bay views from the living area, or enjoy the rare luxury of a privately owned beachside cabana—perfect for storing beach chairs, umbrellas, and all your seaside essentials while keeping Siesta Key's famous white sand where it belongs. Situated in the quieter southern section of the Key, you'll enjoy a peaceful setting while remaining close to local restaurants, shopping, and island activities. Hop aboard the Froghopper or Free Ride Trolley to explore Siesta Key with ease. Bay Tree amenities include: Private beach access to Turtle Beach Two heated pools (beachside and bayside) Grilling and picnic areas Free boat slips for owners Kayak storage racks On-site management Reserved owner parking Ample guest parking Whether you're walking to nearby dining, kayaking on the bay, enjoying a sunset beach stroll, or simply relaxing and taking in the views, this exceptional property offers the best of both bayfront and beachfront living. Seasonal Rates: May 15 – October 31, 2026: $2,300/month November – December 2026: $2,750/month January 2027: $5,000/month Annual Rental Rate: $3,350/month Contact us today for availability and additional details.
1850 WEBBER ST, SARASOTA, FL 34239
$13,00059 Days on yellowkey MLS ID: A4693021
REDUCED by $2,000 (13.3%) on 06/14/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026Community: Poinsettia Park 2Spa: YesSingle Family
Remarks: 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)
1686 CHAPLINE LN, SARASOTA, FL 34231
$3,000235 Days on yellowkey MLS ID: A4672328
REDUCED by $250 (7.7%) on 04/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1963Single Family
Remarks: Available August 1, 2026 60 Day Minimum... 3000.00 annually 3000.00 Discover comfort, convenience, and coastal charm in this fully furnished 3-bedroom, 2-bath home located West of the Trail in the highly desirable and non-deed-restricted community of Bayview Acres. Inside, you’ll appreciate the beautifully renovated kitchen, split floorplan, and thoughtful upgrades throughout. Each bedroom is equipped with a ceiling fan for added comfort, and the impact-rated sliding door opens to a serene screened lanai—an ideal spot to unwind after a day at the beach. The fully fenced, spacious yard offers plenty of room to enjoy the outdoors, along with extra space to store bikes, beach gear, or anything else you bring along. Situated within the tranquil bird sanctuary of Bayview Acres, the home provides a peaceful, nature-filled setting perfect for relaxation. This home is designed to make your stay effortless, with all the details that turn a good Siesta Key/Sarasota getaway into a truly memorable experience. Prime Location: Walk or bike to the beach, shopping, and dining—everything is just minutes away. Available for Weekly and Monthly Stays. Take a look—you won’t be disappointed! January through April 2027- 4500.00 monthly plus taxes and fees.
6215 GREEN VIEW CIR #74, SARASOTA, FL 34231
$1,875113 Days on yellowkey MLS ID: A4687043
REDUCED by $75 (3.8%) on 06/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1973Community: Village In The Pines 1Condo
Remarks: Move-in ready and freshly updated! This 2-bedroom, 2-bath furnished villa in the desirable 55+ community of Village in the Pines features a brand new A/C system and new flooring throughout. Everything you need is already here — furniture, washer and dryer included. Community amenities include a heated pool, clubhouse, and the convenience of lawn maintenance, water, and basic cable all included in rent. Located less than 5 miles from the world-famous shores of Siesta Key, with easy access to Gulf Gate shopping, dining, and everyday conveniences. Bring your suitcase and start living the Florida lifestyle today.
Listing Agent: Lee Brewer (941-724-3448)
3350 S OSPREY AVE #209A, SARASOTA, FL 34239
$1,85078 Days on yellowkey MLS ID: A4691461
REDUCED by $50 (2.6%) on 06/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1969Community: Bermuda On OspreySpa: NoCondo
Remarks: Beautiful unfurnished 2-bedroom, 2-bath condo available for annual rental in the well-located Oasis on Osprey community in Sarasota. This second-floor residence offers elevator access, a spacious living and dining area, a well-appointed kitchen, two comfortable bedrooms, two full bathrooms, and a screened balcony for relaxing outdoor space. The community offers a pool, small fitness room, coin laundry, one assigned parking space, and guest parking subject to availability. The location is one of the strongest features of this condo. It is just minutes from Siesta Key, Southside Village, Sarasota Memorial Hospital, Hillview, Downtown Sarasota, shopping, dining, grocery stores, and everyday conveniences. The Crossings at Siesta Key is approximately two blocks away, making errands, restaurants, and services very convenient. This is a great option for someone looking for a clean, well-located annual rental west of Tamiami Trail with easy access to beaches, medical facilities, downtown Sarasota, and daily conveniences. Annual lease preferred. Unfurnished.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Alberto Garcia (941-730-5205)
2118 MICHELE DR, SARASOTA, FL 34231
$2,000118 Days on yellowkey MLS ID: N6143453
INCREASED by $200 (11.1%) on 06/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 873 Built: 1972Community: MonticelloHalf Duplex
Remarks: Updated and fully furnished turnkey 2-bedroom, 2-bathroom half duplex available with a 6-month minimum lease in one of South Sarasota’s most desirable neighborhoods. This beautifully maintained home features an open-concept floor plan, a stylish updated kitchen with quartz countertops, white cabinetry, and stainless-steel appliances, as well as a spacious primary suite with an ensuite bathroom and walk-in closet. The thoughtfully designed bedroom layout allows the second bedroom and adjacent bathroom to be closed off from the main living area, creating a private guest suite ideal for visitors, roommates, or extended stays. Enjoy Florida living year-round from the screened lanai overlooking a private backyard, perfect for relaxing or entertaining. Ideally located near top-rated Sarasota schools and just minutes from Siesta Key Beach, premier shopping, dining, and everyday conveniences, including Publix, Trader Joe’s, Target, Gulf Gate’s popular restaurants, and Detwiler’s Farm Market. The home also offers quick access to the Tamiami Trail retail corridor and Sarasota’s renowned Gulf Coast attractions. First month, last month, and security deposit required. Water/sewer included. Tenant responsible for electric and cable/internet. Application required.
Listing Agent: Rick Tritschler, Jr. (941-928-1292)
2227 MONTCLAIR DR #1, SARASOTA, FL 34231
$2,300112 Days on yellowkey MLS ID: A4687276
REDUCED by $200 (8.0%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2118 Built: 1970Community: Monticello Unit 1Spa: NoHalf Duplex
Remarks: Great Location on Spacious Corner Lot. Very Clean and Updated Rental Featuring 3 Bedrooms, 2 Bathrooms. Enjoy the Nice Side Drive & 1.5 Car Garage with Laundry Hook-Up, Big Foyer, Newer Kitchen with Breakfast Bar Overlooking Family Room, 3rd Bedroom Can Also Be Used as Office or Work-Out Room, Primary Bedroom has a Private Entrance, Double Closets and Private Bathroom. New Flooring, Paint and All New Lighting. Very Close to Tamiami and Siesta Key...
Listing Agent: Lisa Sanders (773-398-0378)
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