Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
5835 TIDEWOOD AVE #16, SARASOTA, FL 34231
$1,99542 Days on yellowkey MLS ID: A4686821
0 Days Off yellowkey (back on 4/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1355 Built: 1973Community: Baywood Colony Sec 2Villa
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year:
Middle School: Brookside Middle
Remarks: Welcome to your slice of coastal living at 5835 Tidewood Avenue #16 in Sarasota, FL! This charming villa-style residence is perfectly situated west of US-41 in a desirable waterfront community, just minutes from the world-renowned Siesta Key beaches. This well-maintained unit offers a comfortable and functional layout ideal for seasonal or annual living. Enjoy a light and airy interior, complemented by serene surroundings and lush tropical landscaping. The property is nestled near the water, providing a peaceful setting while still being close to everything Sarasota has to offer. Residents will appreciate the convenient location—just north of Stickney Point Road—with easy access to shopping, dining, marinas, and entertainment. Whether you're heading to the beach, exploring local restaurants, or enjoying sunset walks along the water, this location delivers the ultimate Florida lifestyle. Highlights: Prime west-of-41 location near Siesta Key Villa-style living in a quiet, waterfront community Close to shopping, dining, and beaches Peaceful setting with tropical surroundings Perfect for those seeking relaxed coastal living with convenience and charm—schedule your showing today!
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Mike Sorensen (941-380-2900)
1740 LANDINGS BLVD #39, SARASOTA, FL 34231
$3,5001816 Days on yellowkey MLS ID: A4500235
INCREASED by $600 (20.7%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1982 Tax: $3,711 (2021)Community: Landings Carriagehouse ICondo
Taxes:$3,711
Tax Year: 2021
Remarks: Welcome to the gated community of the Landings and the Landings Racquet Club in Sarasota. Not available January 1 - April 30, 2027. Available May through December 2027. Owner requests a 6 month minimum rental. Association rules allow 2 rentals in a calendar year. A rare find to lease this beautiful carriage house condo at The Landings! This two bedroom, two bath +den, one story Carriage House, is where you want to be! Bed sizes are King and Queen. The large living room has designer tile flooring, marble wood burning fireplace, crown molding and park like views leading to a small pond with a fountain and the community pool. The dining area overlooks the living room with new floor tile, crown molding and plenty of room for family gatherings. The sunny bonus room off the dining area is set up as an office with 2 desks and a sofa sleeper for extra company. The master suite has a King bed with newer carpeting, shutters, crown molding, walk-in closet and a remodeled bathroom. The guest bedroom has a Queen bed and the guest bathroom has a tub and shower combination. The eat in kitchen has granite counter tops, tile backsplash, refaced cabinets and all new Whirlpool appliances. There is a delightful small courtyard perfect for morning coffee or outside grilling. There also two outside sitting areas off the Living and master bedroom to enjoy the calm and peaceful views. The Landings Racquet Club membership transfers to the guests. Tennis players will love the Har-Tru tennis courts, and guests will get a good work-out in the lap pool. Relax in the hot tub to soothe sore muscles. The clubhouse has a fitness center, meeting rooms and a library. Guests pay the monthly electric bill on off-season rentals. Off-season rate in effect from May-November.
Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)
Listing Agent: Margaret Young (941-359-3435)
1894 LOMA LINDA ST, SARASOTA, FL 34239
$5,5006 Days on yellowkey MLS ID: A4690884
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 1867 Built: 1954Community: Floyd & Cameron SubSingle Family
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: AVAILABLE MAY 1ST - Unfurnished and annual rental only, is this contemporary gem located West of the Trail in vibrant Sarasota, FL. This spacious home offers a seamless blend of modern design and cozy charm, featuring an open floor plan that is perfect for both entertaining and everyday living. Step inside to discover a beautifully appointed chef's kitchen, complete with solid wood cabinets, sleek granite countertops, and high-end stainless steel appliances. A convenient eating space in the kitchen invites gatherings and casual meals alike. The home boasts three generously sized bedrooms, each with its own en-suite bathroom, offering privacy and convenience for all residents. New carpeting has been added. The expansive lot is a true highlight, with an oversized backyard featuring garden beds and ample private outdoor space, perfect for gardening enthusiasts or those who love to relax in a serene setting. Parking is a breeze with both a garage and driveway. This pet-friendly haven is ideally situated close to Downtown Sarasota, Southside Village, and numerous beautiful beaches such as Siesta Key and Lido Beach. Also this is in the Southside Elementary school district. Enjoy easy access to shopping, dining, and entertainment options, as well as a unique easement providing convenient access to Sarasota Memorial Hospital. Don’t miss your chance to make this your home.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Beth Harris (941-321-7148)
2724 MONTEREY ST, SARASOTA, FL 34231
$3,35052 Days on yellowkey MLS ID: A4682798
REDUCED by $100 (2.9%) on 04/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1384 Built: 1967Community: Bellflower GardensSingle Family
Remarks: AVAILABLE PARTIALLY FURNISHED OR UNFURNISHED. (Please note: Finishing touches will be completed in the next few days. Some photos are virtually staged for illustrative purposes.) Welcome home to this beautifully updated 3-bedroom, 2-bath residence situated on an oversized 1/3-acre lot on a quiet road. This move-in-ready home features newly installed tile flooring throughout, freshly painted interiors, and fully renovated bathrooms with new vanities and showers. Enjoy Florida living at its best with a spacious screened-in outdoor living area and a large 14x28 private pool — perfect for relaxing or entertaining. The expansive lot also offers covered side parking ideal for a boat, RV, or additional vehicles. Conveniently located near A+ rated IB High School and close to shopping, dining, and everyday amenities. Offered partially furnished or unfurnished based on tenant preference. Local, attentive landlord.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
2403 BROWNING ST, SARASOTA, FL 34237
$2,60023 Days on yellowkey MLS ID: A4689230
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1245 Built: 1977Community: Hudson ParkSpa: NoSingle Family
Elementary School: Alta Vista Elementary
Remarks: 3 bedroom 2 bathroom near downtown Sarasota available for rent now. Corner lot with a curved drive way which has an entrance and an exit. Fenced back yard. A court yard right off your door for a morning coffee. Master bathroom has a walk-in shower. Every bedroom has a ceiling fan. This cute home can be rented with the furniture or without furniture. Great locations all within a short distance. Miles of walking and biking trails nearby. Minutes from Siesta Key, downtown Sarasota, shopping center, I-75, 41, etc. Also close to Lido/St. Armand’s Circle. Short walk to Payne Park. Flexible rental terms.
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Tracy Tanovich (941-524-1838)
3239 BENEVA RD #101, SARASOTA, FL 34232
$3,2001525 Days on yellowkey MLS ID: A4526478
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1978Community: Village Brooke Sec 2Condo
Elementary School: Wilkinson Elementary
Remarks: *AVAILABLE FOR 2027 SEASON STARTING 1/1/2027* UP TO A 6 MONTH LEASE* BEAUTIFULLY UPDATED GROUND FLOOR CONDO LOCATED IN THE HEART OF SARASOTA LESS THAN 7 MILES FROM THE STUNNING SIESTA KEY BEACH! This fully furnished seasonal rental is the perfect place to sit back and enjoy your vacation get away. The open floor plan and stunning furnishings give this condo a light, bright, and airy feel. The completely updated kitchen opens up to the living/dining room combo. It is the perfect area to have a great meal with your family or entertain your friends. The master suite offers a king-sized bed and a large walk-in closet. The master and spare bathrooms are completely update with granite counter tops and shower and tub combos. The spare bedroom offers a queen-sized bed and a big closet with plenty of space for your bathing suites. The fully screened in back porch looks out over the gorgeous lake. Village Brooke is centrally located providing access to shopping, restaurants, and a short drive to Siesta Key Beach. **RENT PRICES: **APRIL-DECEMBER $1800**SORRY NO PETS, PICKUP TRUCKS, OR VEHICLES OVER 18 FEET ALLOWED DUE TO HOA RULES** **NEED 15 DAYS PRIOR TO MOVE IN FOR APPLICATION TO HOA -state and local tourism tax applies to any lease 6 months or less, along with application fees, and $250 cleaning fee.**
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Brigette Marcus (941-315-9500)
2832 BAY ST, SARASOTA, FL 34237
$2,35018 Days on yellowkey MLS ID: A4689721
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1958Community: Greenbriar Homes 2Nd AddSingle Family
Remarks: Turnkey Furnished Short-Term Rental Available 5/1/26 - 1/31/27 Only. Recently renovated Mid-Century Modern 3 bedrooms, 2 baths, 1 car garage home just minutes from Downtown Sarasota. Open concept living and dining rooms with cathedral ceilings and wood beams. The Interior and Exterior of the home have been freshly painted. The home has restored Terrazzo flooring throughout. The fully equipped kitchen has new appliances, a pantry, plenty of cabinets for storage, an eat-in countertop that looks out to the living room. The master bedroom has an updated en-suite bathroom with a walk-in shower, the other 2 bedrooms share an updated bathroom with a shower and bathtub. The backyard is fenced and features an amazing paver entertainment area. Walking distance to the YMCA and famous Yoder's Amish Village. Minutes away from world-famous Siesta Key Beach, Lido Beach, St Armand's Circle, museums, and so much more.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)
Listing Agent: Andrew Barnard (941-920-2001)
3755 S SCHOOL AVE #41, SARASOTA, FL 34239
$2,0506 Days on yellowkey MLS ID: A4691238
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972Community: Sunland AptsCondo
Remarks: 55+ Community. First month, last month, and a $500 security deposit required. No pets. Owner pays the association fees, and rent includes cable, water, sewer, trash, and more. Beautifully updated and move-in-ready condo located in the heart of Sarasota, just minutes from world-famous Siesta Key Beach. This 2-bedroom, 2-bath residence offers a bright, open layout with abundant natural light and a comfortable flow for everyday living. The interior features updated flooring, neutral finishes, and a functional kitchen with modern cabinetry, ample counter space, and a breakfast bar that opens to the main living area. The spacious primary suite includes an en-suite bathroom, walk-in closet, and private access to the lanai, while the guest bedroom is well-positioned for privacy with generous closet space. Both bathrooms have been updated with clean, modern finishes. Enjoy peaceful views, creating the perfect setting to relax or unwind. Additional features include sliders, elevator access, and nearby storage and laundry facilities. Located in a well-maintained community with convenient access to shopping, dining, and entertainment, as well as close proximity to downtown Sarasota and the beaches.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
5930 BRIARWOOD AVE, SARASOTA, FL 34231
$9,50034 Days on yellowkey MLS ID: A4687860
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3428 Built: 2022Community: FlorenceSpa: YesSingle Family
Remarks: Live the Florida lifestyle in this stunning newly built coastal contemporary home, just mintures from world-famous Siesta Key Beach. Designed for both comfort and style, this spacious residence offers over 3400 SF of beautifully finished living space with 4 bedrooms, 4 full bathrooms and a versatile 1,100 SF bonus room, perfect for movie nights, billiards, ping pong, etc. It features floor-to-ceiling glass walls and a dramatic 31' NanaWall system seamlessly blends indoor and outdoor living. Open the doors to your private backyard oasis featuring a custom resort-style pool, sun shelf and a luxurious raised infinity-edge-spa, ideal for relaxing or entertaining. The heart of the home is the designer kitchen, showcasing an oversized quartzite island with waterfall edge, perfect for gathering with friends and family. The adjacent living area boasts soaring 13' vaulted ceilings. The primary suite is a private retreat with motorizes shades, dual walk-in closets and spa-like bathroom finishes.
Listing Agent: Kelly Anderson (941-320-6115)
9397 MIDNIGHT PASS RD #405, SARASOTA, FL 34242
$2,400240 Days on yellowkey MLS ID: A4663823
REDUCED by $200 (7.7%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1975Community: Pointe On Midnight PassSpa: YesCondo
Remarks: Here’s is your chance to live on the SOUTHERNMOST TIP OF SIESTA KEY and enjoy STUNNING SUNRISES & SUNSETS all year long. This WATERFRONT RENTAL is located at The Pointe, the CLOSEST CONDO complex to MIDNIGHT PASS! This one-of-a-kind gated community encompasses over 5+ acres of PRIME WATERFRONT real estate and is loaded with amenities including tennis, pickleball, fitness center, heated lap pool, spa, dry sauna, kayak launch, clubhouse and more. Boat docks are also available for a small fee on a first come first serve basis. Rather go to the beach? No problem…Turtle Beach access is just a half-mile away. And let’s not forget, just a few miles up the road are all the amazing restaurants and shops of Siesta Village. The first thing you’ll notice when you enter this turnkey-furnished, 2bed/2bath condo, is how the living area leads right out to an expansive 30-foot lanai overlooking Little Sarasota Bay and the Jim Neville Nature Preserve…a perfect spot for entertaining or just sitting back and enjoying the view and the wildlife. The primary bedroom also has access to the lanai and features an ensuite bathroom, finished closets, and of course, spectacular sunrise views. Engineered hardwood floors throughout give the home a cozy, beachy feel. Unlike other condos in the area, a washer/dryer is conveniently located within the unit. Recent updates include 5 new ceiling fans, new blinds, new range, newer dishwasher, and new furniture in the dining room and living room. AC was replaced in 2019. There is also additional storage space on the ground floor for all your beach and boating gear. Sorry, no pets allowed. Rental applications must be received 21 days prior to any occupation. **Long-Term Rental (minimum 7 months) = $2400/month ~ Short-Term Rental (minimum 3 months) = $6500/month.
Listing is courtesy of: UKEEPCOMMISSION REAL ESTATE (941-465-9206)
Listing Agent: Adam Waxler (941-465-9206)
2216 WEBBER ST #C, SARASOTA, FL 34239
$1,6005 Days on yellowkey MLS ID: A4688118
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)
4879 COMMONWEALTH DR, SARASOTA, FL 34242
$14,500300 Days on yellowkey MLS ID: A4657954
INCREASED by $500 (3.6%) on 04/24/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2450 Built: 1957Community: Siesta BeachSpa: NoSingle 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)
1750 BENJAMIN FRANKLIN DR #9B, SARASOTA, FL 34236
$9,400146 Days on yellowkey MLS ID: A4674245
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1364 Built: 1970Community: Key Tower SouthCondo
Remarks: GULF-FRONT LIDO KEY LUXURY • REAL OPPORTUNITY • $6,200/month. AVAILABLE NOW MAY-DECEMEBER 2026 at OFF SEASONAL RATE! - IN-SEASON RATE (JAN-APR) IS $9,400/MO. Availability for 2027 is APRIL - DECEMBER. Wake up to rolling waves and end every day with a front-row sunset over the Gulf of Mexico. This ninth-floor, full Gulf-front condo delivers panoramic water views that are just breathtaking— Promotional OFF Seasonal Rate: $6,200/month • Valid for May thru December 2026 only. In-Seasonal Rate of $9,400/month. Located in the distinguished Key Towers South on Lido Key, this fully furnished residence places the beach quite literally at your doorstep—and Sarasota’s St. Armand's best dining, shopping, and culture just minutes away. Inside, the open-concept layout is designed for comfort and effortless coastal living. The kitchen features granite countertops, stainless steel appliances, and fully stock with all the necessities for a gourmet meal. A dedicated office/den offers an ideal remote-work setup - perfect for quick emails, travel planning, or looking up that sunset cocktail recipe. The true showstopper is the enclosed Gulf-front balcony—a light-filled extension of the living space where the shoreline becomes your daily backdrop. Morning coffee hits differently here. So do sunsets. The primary suite is a serene coastal retreat with generous closet space and a private bath, while a separate guest suite ensures comfort and privacy for visitors. Additional features include: Impact-rated windows throughout Multiple interior storage closets Shared utility room with washers & dryers on the same floor Dedicated storage locker Residents of Key Towers South enjoy recently updated amenities, including: Renovated lobby and first-floor social spaces (2025) Fitness room, library, and social room with catering kitchen Sauna and shower facilities Bike storage Gulf-front pool and lounge deck with unforgettable sunset views Perfectly positioned between the Gulf of Mexico and Sarasota Bay, this condo places you at the center of Lido Key’s coastal lifestyle: South Lido Park — just ¼ mile away St. Armand's Circle — one mile north Downtown Sarasota — four miles over the Ringling Bridge Easy access to the free Sarasota Bay Runner bus for effortless exploring. NOTE: January–March 2027 is already booked.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Norma Mladineo (941-363-1588)
2849 MARLETTE ST, SARASOTA, FL 34231
$2,09536 Days on yellowkey MLS ID: A4687402
REDUCED by $100 (4.6%) on 04/18/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1008 Built: 1949Community: Sarasota-Venice Co SubSingle Family
Remarks: Adorable 2 bedroom 1 bath home in central location, close to beaches, downtown Sarasota, I-75, St. Armand's Circle, and many restaurants and shopping options. Beautifully updated kitchen with custom cabinets and Quartz countertops, updated bath with walk in shower, new vanity, laminate flooring throughout the home, and newer furniture with a coastal living vibe. A fully fenced backyard makes this a perfect home for family entertaining or for pets. Short term or annual lease options. Home is situated at the end of a dead end street for added privacy.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jennifer Bright (941-320-4989)
1624 STICKNEY POINT RD #108, SARASOTA, FL 34231
$2,2007 Days on yellowkey MLS ID: A4690440
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1016 Built: 1975Community: Castel Del MareSpa: YesCondo
Elementary School: Gulf Gate Elementary
Remarks: Discover the epitome of island living in this inviting 2-bedroom, first-floor condominium, perfectly positioned a short distance from Siesta Key—offering the ideal blend of comfort and convenience in beautiful Sarasota. Nestled within a sought-after resort-style community along the Intracoastal Waterway, residents enjoy exceptional amenities including two heated pools! One is located right on Sarasota Bay—with breathtaking water views and unforgettable sunsets await. Additional features include a bayside gazebo, kayak racks with launch area, tennis courts, pickleball courts, shuffleboard, and a scenic boardwalk that wraps around the bay. Inside, the thoughtfully designed layout offers both comfort and functionality. The primary bedroom features a queen-sized bed, generous space, and a private ensuite bathroom, while the second bedroom includes two full beds and ample closet storage. The well-appointed kitchen flows seamlessly into the cozy living area, creating a welcoming space for relaxation or entertaining. Location is everything—and this home delivers. Enjoy a short 12-minute walk to the world-famous Siesta Key Beach, or take a quick 10-minute stroll to nearby dining, shopping, and recreational activities including jet ski rentals. Embrace the island lifestyle by biking to Siesta Key Village or hopping on the free trolley after a scenic walk over the bridge. Additional convenience includes a laundry room just steps from the unit. Leave your car behind and enjoy the ease of walkable coastal living. Seize the opportunity to experience your own slice of paradise—monthly rates vary by season, please inquire for accurate pricing.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
301 AVENIDA MADERA #B, SARASOTA, FL 34242
$12,6007 Days on yellowkey MLS ID: A4690443
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1970Spa: NoSingle Family
Remarks: Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright open floor plan with a relaxed coastal theme, a fully equipped kitchen featuring granite countertops, stainless steel appliances, and a Keurig coffee maker, plus a spacious dining area overlooking a peaceful canal. The home comfortably sleeps up to 6 guests with a queen-size sofa bed and an auto-inflatable queen EZ bed, while the primary suite includes a private full bathroom. Step outside to enjoy true Florida living—grill out, swim, sunbathe, or fish right from the canal, and don’t forget your furry companions as this property is extremely pet-friendly. The shared pool area (with Unit A) adds to the experience, while both units has private entrances with no shared interior walls, ensuring added privacy. For peace of mind, exterior security cameras are in place, and the unit is strictly smoke-free with no indoor smoking permitted. Whether you're walking, biking, or taking the trolley to Siesta Key Village, everything you need is within reach—making this an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle.
301 AVENIDA MADERA #A, SARASOTA, FL 34242
$12,6007 Days on yellowkey MLS ID: A4690447
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1970Community: Siesta Manor Sec 1Spa: NoSingle Family
Remarks: If you’re searching for the perfect location for your next vacation, your search ends here! This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid surface countertops, stainless steel appliances, and a charming breakfast nook. The spacious primary suite offers a king-sized bed and a private en suite bathroom with a walk-in shower. A standout feature of this home is the private rooftop deck, complete with outdoor furniture, a grill, and umbrellas for shielding the sun- perfect for enjoying sunny afternoons or relaxing evenings while taking in stunning sunset views over Siesta Key Beach. During the day, enjoy the convenience of walking to the beach, local shops, and restaurants, or take a short drive over the bridge into Sarasota for even more dining, shopping, and entertainment options. This pet-friendly home is ideal for family gatherings, and for larger groups, Unit B can also be rented for additional space. The pool area is shared with the neighboring unit, while both units maintain privacy with separate entrances and no shared interior walls. The home is strictly smoke-free with no indoor smoking permitted. Enjoy your stay in this exceptional island retreat!
3664 TIN CUP BLVD, SARASOTA, FL 34232
$2,450170 Days on yellowkey MLS ID: A4671629
0 Days Off yellowkey (back on 4/23/2026)
REDUCED by $50 (2.0%) on 04/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 2016Community: Enclave/Frst LakesVilla
Remarks: Welcome to this beautifully appointed 2-bedroom, 2-bath end-unit villa on a premium corner lot directly across from the resort-style community pool in the gated community of The Enclave at Forest Lakes in Sarasota. Offering nearly 1,600 square feet of bright, open living space, this freshly painted home is available for annual lease. The gourmet kitchen is perfect for entertaining, featuring granite countertops, a large island, abundant cabinetry, and stainless-steel appliances—including a built-in oven, microwave, and range with hood. The open-concept design flows seamlessly into the spacious living area, highlighted by high ceilings and abundant natural light from large windows throughout. The primary suite serves as a private retreat with a walk-in closet, dual-sink vanity, and walk-in shower. A full dining room and a second bedroom with a built-in Murphy bed add flexibility and function. Additional highlights include tile and carpet flooring, a full-size washer and dryer, a two-car garage, and a covered lanai perfect for relaxing outdoors. Lawn care and trash service are included for your convenience. Residents of The Enclave at Forest Lakes enjoy resort-style amenities, including a sparkling pool and beautifully maintained grounds. Ideally located in the heart of Sarasota, this home is just minutes from I-75, world-renowned Siesta Key Beach, downtown Sarasota, and the shops and dining of St. Armands Circle.
Listing is courtesy of: MCGREGOR INTERNATIONAL REAL ESTATE CO (941-363-1210)
Listing Agent: Warren Mcgregor (941-447-1253)
5738 ANTILLES DR, SARASOTA, FL 34231
$2,950248 Days on yellowkey MLS ID: A4662529
REDUCED by $1,000 (25.3%) on 04/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1834 Built: 1971Community: Phillippi Gardens 03Spa: NoSingle Family
Remarks: Available after May 10th , 2026 for up to ONE YEAR! Fully Furnished with Private Fenced Yard This single-family home is located within minutes of Siesta Key Beach. This charming 4-bedroom, 2-bath home with an attached 2-car garage is situated in Phillippi Gardens. Enjoy a walk or bike ride to Phillippi Estate Park to take advantage of nature trails, fishing piers, a playground, and the weekly farmer's market. The home is conveniently located near shops and restaurants. A fenced yard, laundry room, rear patio, and Florida Room make this a great spot to enjoy Sarasota! The owner will consider a longer-term lease. From January through April of 2026, the rental rate is $4,500.00/month plus tax.
2410 CASS ST, SARASOTA, FL 34231
$3,250160 Days on yellowkey MLS ID: A4672343
REDUCED by $1,250 (27.8%) on 04/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1624 Built: 1971Community: Gulf Gate WoodsSpa: NoSingle Family
Remarks: Available month-to-month June 1, 2026 through December 2026, this beautifully updated Gulf Gate Woods pool home is one of Sarasota’s most sought-after retreats. Fully furnished and designed for comfort, this 3-bedroom, 2-bath home sits on an oversized lot in the serene Gulf Gate Woods neighborhood and features updated hurricane doors and windows for added security and peace of mind. The thoughtfully designed split floorplan, ceramic tile throughout, and whole-house water filtration system enhance the home’s luxury feel. Enjoy seamless indoor-outdoor living with a private heated, caged pool accessible directly from the primary suite, guest bedroom, and main living area—perfect for swimming, lounging, or relaxing in an insect-free outdoor oasis. The large backyard is ideal for cookouts and gatherings, while the quiet residential location places you close to everything Sarasota has nearby, from scenic bike rides through Gulf Gate Woods to beautiful beaches just minutes away. Your stay includes Wi-Fi, air conditioning, water, trash removal, laundry, lawn service, and pool maintenance, ensuring a hassle-free experience from start to finish. Now available June 2026 through December 2026—don’t wait, this exceptional home will book quickly. Secure your stay today!
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