Remarks: AVAILABLE OFF-SEASON RATE MAY THROUGH END OF DECEMBER 2026 & MARCH & APRIL 2027: EXCEPTIONAL VILLA at Stoneybrook G&CC on the golf course, three bedrooms, two baths, and two-car garage. A transferable golf membership is available if desired for a fee payable to the country club. The entryway is screened and is nicely furnished with comfortable seating; step into an open floor plan with breakfast nook and well-designed kitchen featuring stone countertops, a storage pantry, high-end appliances, and opens to the dining area. The dining area is also open to the living room, offering comfy leather seating, a smart TV, and a view from the living room onto an inviting lanai overlooking the 5th fairway. The master bedroom has a king-sized bed, an ensuite bathroom with a garden tub and vanity with twin sinks, plus a nicely tiled and glassed walk-in shower. There is a king bed in the second bedroom, which is located adjacent to the guest bathroom, and the 3rd bedroom can also function as a den/office and has twin beds for the occasional guests, a closet, and a desk area with storage cabinets. The large extended lanai has a covered area for seating and a caged screened area, making it perfect for entertaining. The two-car garage has room for your vehicle, beach toys, and there is a utility sink for added convenience. A community pool is located just a couple of blocks away. Stoneybrook is a gated community conveniently located on Palmer Ranch featuring a newly modernized Kipp Schultes-designed golf course, said to be one of the best courses on the west coast of Florida, a fitness center, a large heated pool, a state of the art clubhouse featuring fine and casual dining, Har Tru tennis courts, bocce ball, and the community borders the Legacy walking and biking trail access, is less than 15 minutes from the sugary sandy beaches of Siesta Key and the village shops and restaurants. There is a local YMCA and a park with 6 pickleball courts, a Costco and Publix all within a couple of miles from the community, and you can be downtown Sarasota in 25 minutes to take in the cultural and culinary activities that Sarasota offers. Call for more information and for off-season rates.

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)

Listing Agent: Vicki Reilly (941-266-5962)

Remarks: ANNUAL, UNFURNISHED RENTAL. Step into refined Florida living in Windward, where a smart, open layout pairs everyday comfort with easy entertaining. The cook’s kitchen anchors the home with soft-close cabinetry, under-cabinet illumination, oversized sink, and a gas range, flowing seamlessly into a generous great room framed with a coffered ceiling. Durable tile floors in main living areas and Luxury Vinyl Plank flooring in bedrooms and den, complemented by upgraded lighting, and 8' interior doors all provide for a clean, elevated feel. Need a quiet spot to focus? The double French-door entry into your den/flex room is ideal for work, hobbies, or guests. The private primary suite features two closets (one walk-in), a ceiling fan, and a refreshed en-suite with an upgraded shower. Thoughtful quality continues with WHOLE HOUSE IMPACT WINDOWS AND DOORS and blinds on all windows...no hassling with shutters! Outdoor living shines: relax on the extended, screened lanai with pavers and ceiling fan, taking in treed scenery with a water view—perfect for morning coffee and evening cocktails. It’s plumbed with a dedicated gas line for grilling, and rear/front hose spigots for everyday convenience. And everyday living is made easy with a spacious laundry room and a two-car garage with a utility sink. Other thoughtful updates include added insulation in the exterior block walls and garage doors, closet organizer systems, and window tint for efficiency. Windward living means resort perks: resort-style pool and splash pad, spa, modern fitness center, 8 pickleball courts, 2 tennis courts, sports fields, clubhouse, dog parks, playgrounds, miles of trails, and a full-time activities director. With direct access to Waterside Place and quick reach to Lakewood Ranch Main Street, downtown Sarasota, I75, premier beaches, dining, culture, and championship golf, you’re at the center of it all. Crisp, move-in ready, and thoughtfully upgraded—come see why this villa stands out

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)

Listing Agent: Joanna Benante (941-356-7718)

Remarks: An Ascendia Group Property! Discover modern luxury living in the heart of Gracewater at Sarasota the area's most exciting new master-planned community! This brand-new 2-bedroom, 2-bath home (paired villa style) plus den is available as an annual rental, offering the perfect blend of coastal sophistication, and low-maintenance convenience– all just under 10 minutes from vibrant downtown Sarasota. Spacious open-concept layout with high-end finishes, abundant natural light, and contemporary design. Resort style amenities feature a community pool with cabanas, fitness center, pickleball courts clubhouse and dog park (coming soon or now open).

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: Completely renovated standalone villa located in an private cul-de-sac in The Meadows. Unfurnished, annual rental that lives like a single-family home and has a 1 car garage plus additional parking in the driveway. This home has been renovated and updated top to bottom offering 2 bedrooms, 2 bathrooms, a den, a living room, and a gorgeous kitchen with large work island that is sure to make any cook very happy. Bonus feature is the amazing wet bar with separate icemaker, sink, and wine/beverage cooler. The owner spared no expense when designing the kitchen which includes subzero refrigerator, Wolf appliances, high end granite counters and amazingly rich wood cabinets throughout. The interior laundry room offers ample cabinets for extra storage and stacked, full size washer and dryer. Plantation shutters adorn the impact glass windows, lending to elegance and security. Other features include: surround sound speakers, tile roof, walk-in closets in both bedrooms, exterior security cameras, and beautifully updated bathrooms with walk-in showers. The community offers pools, hot tub, fitness, restaurants, pickleball, gardens, biking and walking trails, basketball court, fishing, community events, playground, golf and so much more (certain membership fees apply). The owner is providing a monthly professional cleaning at no additional cost to the tenant. Vehicle restrictions for driveway parking (trucks must be garaged at night) and sorry-- no pets. Two applications- credit and background check plus approval with association required.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Amy Chapman (941-225-1500)

Remarks: Discover your dream home in the heart of Sarasota's winter paradise! This stunning attached water view single story villa offers 2 bedrooms, 2 bathrooms, and a versatile den, perfect for work or relaxation. Spanning 1,533 square feet, this elegant residence is situated within the prestigious Esplanade at Skye Ranch community. Available for a 12-month lease starting April 15, 2026 or later, this home blends luxury, comfort, and convenience. Just a short drive from the world-renowned Siesta Key Beach, often voted the #1 beach in the U.S., this villa provides the ideal retreat to bask in Sarasota's warm climate. Enjoy peaceful walks through beautifully landscaped paths, or simply unwind in the tranquil ambiance of your new neighborhood. Embrace the Florida lifestyle with premium amenities, modern design, and the perfect location for outdoor enthusiasts. Lease approval is contingent on HOA approval. Don’t miss your chance to live in one of Sarasota’s most sought-after communities!

Listing is courtesy of: IMPERIAL PROPERTY GROUP LLC (941-726-1740)

Listing Agent: Olga Smith (941-726-1740)

Remarks: Welcome to Sarasota’s desirable 55+ Lakeshore Village community. This beautifully maintained, turnkey-furnished 3-bedroom, 2-bath villa offers a spacious and inviting layout with generously sized bedrooms and tastefully updated bathrooms. Ideally situated on a quiet cul-de-sac, the home features a 2-car garage along with ample driveway parking. Multiple skylights fill the space with an abundance of natural light by day and soft moonlight by night, while the private backyard setting provides a peaceful retreat for nature lovers. The versatile third bedroom is currently configured as a den or office, complete with convenient pocket doors for added flexibility. The bright, eat-in kitchen is thoughtfully updated with granite countertops, pull-out drawers, a new sink, recessed lighting, and select stainless steel appliances. Enjoy peace of mind with recent upgrades including a new hot water heater, front-loading washer, and a high-efficiency HVAC system. Freshly painted throughout, the home features updated ceilings finished in a timeless skip trowel texture. Start your mornings in the Florida room, where you can enjoy coffee while overlooking the tranquil private garden as the sun rises. Lakeshore Village offers an active and welcoming lifestyle with scenic lakes and fountains, tennis courts, a saltwater pool, and a clubhouse with a library and a full calendar of social activities. Contact us today to schedule your private showing. No pets, no smoking, and no truck parking permitted in the driveway. Renter’s insurance required. Minimum lease term is 6 months plus 1 day. First month’s rent, last month’s rent, and security deposit due at lease signing. Basic cable and internet are included through the HOA (tenant responsible for any upgrades). Water included up to $70/month and electric up to $95/month.

Listing is courtesy of: EXIT KING REALTY (941-497-6060)

Listing Agent: Patrice Davis (941-270-2156)

Remarks: Large villa with a unique floor plan features 3 bedrooms and 2 baths. Tiled flooring throughout, a beautifully updated kitchen, both baths are updated as well. Access the rear screened lanai through either the living room or family room. An atrium patio located between the living room and master bedroom offers a quiet relaxation place for enjoying the sun. This area is also a great place for the plant enthusiast to enjoy a little gardening. The fenced area between the large 2 car garage and villa is a paver patio sanctuary perfect for setting up a grill or outdoor table and chairs for dining and is accessible from the family room. Side by Side washer and dryer are neatly tucked away in a laundry room. Close to the UTC Mall, downtown Sarasota and all the city's attractions as well as many fine places to dine. Enjoy the Country Club of The Meadows with miles of walking trails, golfing, tennis, pickleball and a fitness center.

Listing is courtesy of: REALTY SERVICES INC (941-954-4443)

Listing Agent: Shirley Cuddy (941-321-1549)

Remarks: Sleek. Modern. Immaculate. Just listed in the fabulous and intimate community of "The Preserves at Palm Aire" this split plan villa features an open concept and is light, bright and beautifully updated with thick stone counters, crisp white cabinets, very nice fans and fixtures and gorgeous wood plank style tile. Smart floorplan. Expansive and private front courtyard makes for a wonderful entertaining space.. back lanai overlooks deep green space with tennis courts in the distance. Large 2 car garage with recently finished epoxy floor. Lovely and vibrant community with a pool for your use, maintenance free lawn care, lush landscaping and a location that can't be beat. Just moments to the fabulous UTC mall, the new Whole Foods, Fresh Market, fantastic dining options and just 15 minutes to downtown Sarasota and the world famous sugar sand beach of Siesta Key. The optional Palm Aire Country Club is within walking distance. There are two 18 hole golf courses, fitness center, 10 tennis and pickle ball courts, Jr.. Olympic size heated pool and a fun clubhouse with a scrumptious Sunday brunch and other activities throughout the year. Come and live the Florida dream in one of the best cities you could ever find.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Teresa Ribaudo (941-376-4500)

Remarks: 3 month stay required. Available Jan-March 2026. Come experience the peaceful and convenient lifestyle offered by this charming 2 bedroom, 2 bath villa located in the desirable Woodside South community. Tucked away in a quiet cul-de-sac, this home boasts mature landscaping that creates a tranquil park-like setting. Enjoy your morning coffee in the cozy dining area or spend your evenings relaxing on the lanai. Centrally located near dining, shopping, and beautiful Siesta Key Beach.

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: This is a spectacular FURNISHED 2 bedroom 2 bath PLUS DEN Villa in Gated, Sunrise Preserve at Palmer Ranch. This property is in "model like" condition ~ just pack you bags and move right in. This immaculate property, built in 2020, has a great open floor plan, fantastic Kitchen, nice den/office and large bedrooms. Sunrise Preserve is an amenity filled community featuring a clubhouse with activities, fully equipped fitness center, tennis courts, bocce courts, pickleball courts, fire pits, and a resort style heated pool & spa.

Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)

Listing Agent: Tony Andrews (941-921-5999)

Remarks: Welcome to this beautifully appointed Esplanade at Skye Ranch turn-key furnished 2-bedroom, 2-bath villa with a 2-car garage located in the highly sought-after Esplanade at Skye Ranch. This light and bright home offers an open layout, stylish furnishings, and a low maintenance lifestyle—perfect for those seeking comfort and convenience. Residents of Skye Ranch enjoy access to an impressive lineup of amenities, including the Skye Ranch Hub, resort-style pools, state-of-the-art fitness center, pickleball and tennis courts, basketball, sand volleyball, and the expansive Bark Park. Outdoor enthusiasts will love the miles of nature trails, scenic lakes, and beautifully landscaped community spaces. Located just minutes from top-rated schools, shopping, dining, and I-75. This villa's community is designed to provide a lifestyle that combines the natural beauty of the area with the excitement of resort-style living. Esplanade communities are popular in Southwest Florida, offering a blend of modern homes, resort-style amenities, and a lifestyle that feels like a permanent vacation.

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Melissa Rogier (941-822-8283)

Remarks: Big Price reduction - Owner says get it rented. Annual Rental in Glen Oaks Manor – Sarasota, FL 2 Beds | 2 Baths | 2-Car Garage | Courtyard Pool | Split Floor Plan Nestled beneath a canopy of mature oaks in the highly sought-after enclave of Glen Oaks Manor, this elegant courtyard pool residence offers a rare blend of privacy, comfort, and convenience. Designed with a thoughtful split-bedroom layout, the home features two spacious bedrooms, two full baths, and a two-car garage—ideal for professionals, couples, or seasonal residents seeking year-round tranquillity. Step into your own private oasis, where the screened lanai and covered patio overlook a sparkling pool framed by lush landscaping. The open-concept living and dining areas flow seamlessly into the courtyard, creating a serene indoor-outdoor lifestyle perfect for entertaining or quiet reflection. Prime Sarasota Location, Minutes from world-renowned beaches including Lido Key and Siesta Key, Easy access to downtown Sarasota, UTC Mall, and St. Armands Circle, Close to parks, golf courses, dining, and cultural venues Rental Details Offered as an annual lease, professionally managed for peace of mind, Exceptional value in one of Sarasota’s most established communities This is more than a rental—it’s a lifestyle upgrade. Schedule your private showing today and experience Glen Oaks Manor living at its finest.

Listing is courtesy of: VETERANS REALTY INC. (941-730-3605)

Listing Agent: Gary Benjamin (941-730-3605)

Remarks: This 2-bedroom, 2-bath villa with a 2-car garage is located on a quiet waterfront lot in the sought-after, gated resort-style community of VillageWalk. This extended Capri III floor plan offers extra living space and a bright, open layout. The great room features vaulted ceilings, abundant natural light, and direct access to the screened lanai where you can relax and enjoy peaceful water views. The open kitchen includes Corian countertops, tile flooring, plenty of cabinetry, and a convenient closet pantry. The master bedroom suite has a walk-in closet, dual vanities, and a tiled shower. The second bedroom suite has a private bath and a walk-in closet. An extended den area provides flexible space for a home office, fitness area, or hobby room. Additional highlights include a laundry room with utility sink, upper cabinets, and storage closet. VillageWalk amenities include: full time activities coordinator, two geothermal heated pools, 6 Har-Tru tennis courts, pickleball, bocce, basketball, a state-the-art fitness center, a cafe’ and bar along with a poolside Tikibar, a hair salon, gift store, a private gas station and scenic walking and biking paths throughout the community’s lakes and bridges. You can enjoy all of this as a resident in VillageWalkLocated just minutes from Siesta Key Beach, Legacy Trail, shopping, dining, and Costco—this is Sarasota living at its best! Make a showing appointment today.

Listing is courtesy of: TOWN CENTER REALTY (941-929-9333)

Listing Agent: Scott Albert (941-929-9333)

Remarks: Welcome to your spacious lakeside retreat in Lakeshore Village, a vibrant and highly desirable 55+ community known for its scenic lakes and exceptional amenities. Perfectly positioned in a peaceful waterfront setting, this 1,720 sq. ft. villa offers a wonderful blend of comfort, style, and tranquility. The home has been recently refreshed with new interior paint, new carpet in the bedrooms, and beautifully renovated bathrooms, and is available furnished or unfurnished for an annual lease. Featuring 2 bedrooms and 2 fully renovated bathrooms, this villa provides a seamless indoor–outdoor living experience with peaceful lake views from the private lakeside patio, an ideal space to relax and enjoy the tranquil setting. A spacious two-car garage adds convenience along with generous storage. Inside, vaulted ceilings, skylights, abundant natural light, and expansive sliding glass doors create a bright and airy atmosphere while highlighting the calming water views. The open-concept layout connects the great room and dining area to a well-designed kitchen, creating an inviting space for both everyday living and entertaining. Both the primary and guest suites are generously sized, featuring large walk-in closets and newly renovated bathrooms with modern finishes, adding style and comfort to the home’s thoughtful updates. Residents of Lakeshore Village enjoy a resort-style lifestyle with amenities that include a heated saltwater pool, clubhouse, tennis and pickleball courts, and a billiard room. 6094 Wilshire Blvd. is a true gem, offering a quiet lakeside location in the heart of Sarasota, with the home situated directly on the lake in a peaceful setting. Don’t miss the opportunity to enjoy relaxed lakeside living in one of Sarasota’s welcoming 55+ communities—your new home sweet home awaits!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Dianne Anderson (941-350-3513)

Remarks: Stunning newly renovated 1 bed/1 bath in idyllic Bunker Oaks in The Meadows of Sarasota, a Country Club Community. This gem has been completely updated with high end finishes and is the perfect spot for a single or a couple. Queen bed, flat screen tv's, stainless steel appliances, bright and uncluttered... this unit has it all and it is just off the golf course and steps to the community pool and grilling/picnic area, tennis, fitness facility, miles and miles of walking, hiking and biking trails, nature preserve, butterfly gardens, mature flora and fauna everywhere you look, with both shopping and fine dining just around the corner. Short distance to all of the shopping and dining of University Parkway and St. Armand's Circle, as well as the breathtaking area beaches, including World Famous Siesta Key Beach. Utilities, cable or streaming tv and WIFI included. Association application and approval required ($100 application fee). NO PETS/NO SMOKING. 30 day minimum stay required however, Agent reserves the right to only accept 3 month minimum rentals during the high season months of December - April. RATES: DEC 1-APR 30: $2700 per month* // MAY 1-NOV 30: $1400 per month* (*additional fees & taxes apply). Prices shown are based on 2-person occupancy. Additional persons staying in the unit for a period of longer than 7 days may be considered additional occupants and subject to additional rental fees being charged and/or application and approval process if the community is governed by association rules and regulations. Your rental Agent must be advised of all additional occupants and dates they will be in the unit. Rates include all utilities including WIFI. Additional charges will be: security deposit ($500), departure cleaning fee ($250), Booking fee ($250.00) , Sales and Resort Taxes (13%) and Travel Insurance (if purchased at the time reservation is booked). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received. NOTE: We do not accept reservations for high season months of Jan - April for less than 90 days until after Labor Day. After Labor Day - 30 DAY minimum rentals only during the HIGH SEASON months of January, February and March. Tenants who are in this year have first option to renew for the next year, and have until April 15 to advise us if they are returning. Please contact us to be added to automatic e-mail alerts for available units. PROPERTIES ARE SET UP FOR CONVENIENT CONTACTLESS TOURS. We are unable to do in person showings due to existing bookings and owner usage. Photos on website are updated regularly.

Listing is courtesy of: WAGNER REALTY (941-727-2800)

Listing Agent: Sandra Greiner, Pa (941-879-9410)