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.

Listing is courtesy of: SHOWTIME REALTY (941-822-0890)

Listing Agent: Robert D. Bevington (412-671-3142)

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!

Listing is courtesy of: SHOWTIME REALTY (941-822-0890)

Listing Agent: Robert D. Bevington (412-671-3142)

Remarks: Welcome to Treetops! Complete with 3-Beds, 2-Baths, a large 2-car garage, and a fenced-in yard. The kitchen features plenty of cabinet and counterspace, including a breakfast bar for casual dining, and a utility pantry featuring a washer and dryer and additional storage shelving. Appliances include a stainless-steel microwave, refrigerator, range, and dishwasher. The open floor plan creates an airy, spacious feel, while ample windows fill the home with natural light. Additional details include tile flooring, ceiling fans, and unique built-in shelving. The spacious primary suite features a large walk-in closet and en suite bathroom with a lovely vanity space and walk-in shower. Two additional bedrooms, with one functioning as a home office, and a shared bathroom complete the interior of this home. Pets accepted, (2) pets welcome, and no dangerous breeds. Basic cable and lawn care are included in the rent. Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full months rent! Located at the intersection of Tallevast and Lockwood Ridge, the Treetops at North Forty is a picturesque community with mature landscaping, ponds, swimming pool, and tennis court. Just a short distance away from University Town Center and Lakewood Ranch. PMI Southwest Florida has partnered with Obligo a security deposit alternative to qualified renters! Ask us about this option. 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.

Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)

Listing Agent: Mj Loparco (941-216-0022)

Remarks: TURNKEY FURNISHED. NOT AVAILABLE FOR AN ANNUAL LEASE. Available May 1, 2026 through December. Turnkey furnished, very comfortable and well- equipped single-family home in Gulf Gate area. Nicely decorated and updated kitchen and baths, tile floors throughout, walk-in showers, inside laundry, eat-in kitchen all make for a very comfortable stay. Large, fenced yard, outdoor shower and screened area for outside enjoyment. This home has 2 Queen beds and bunk beds in the third bedroom. Located close to Siesta Key Beach, SMH hospital, Downtown, and easy access to I-75. Pets are welcome with breed restrictions. Tenant will be responsible for electric, cable TV and internet and billed by Stringer Management monthly. $2295. is the off-season rate. Please call for availability.

Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)

Listing Agent: Maureen Plichta (941-812-5799)

Remarks: WEST OF THE TRAIL, BUILT IN 1926! Historic home near the north bridge going to Siesta Key. Cozy and quaint historical home minutes from the Siesta Key and Hillview. Step back in time in this cozy and relaxing home. Wonderful library. Enclosed garden/courtyard. Garage not available. Non smoking. No long term rentals available.

Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)

Listing Agent: Robin De Busk (941-922-4959)

Remarks: **Completely Furnished Rental For Short Term Stays** Forget your worries and unwind in this peaceful, private escape just minutes from the world-famous Siesta Key Beach. This cozy 3-bedroom, 2-bathroom home sleeps up to 10 guests and offers everything you need for a relaxing Florida getaway. Sit back and relax in the front living room or the back sun drenched living room

Listing is courtesy of: TREND REALTY (941-928-3449)

Listing Agent: Joshua Blank (941-928-3449)

Remarks: **Completely Furnished Rental For Short Term Stays** Beautiful 3 bed home 4 miles from Siesta Key Bridge! Comfortably sleeps 8 guests. Two bedrooms with King sized beds and third bedroom with 1 queen bed. Pull out coach and roll away bed. 1 Full bath. Fully fenced in backyard perfect for a nice relaxing dip in the hot tub. Less than 5 miles, about a 10 minute drive to Sarasota Memorial Hospital! 15 minute Drive to The Legacy Trail!

Listing is courtesy of: TREND REALTY (941-928-3449)

Listing Agent: Joshua Blank (941-928-3449)

Remarks: Charming furnished vacation rental in South Gate, a great mid-town location! This freshly painted home has many updates, offering 3 bedrooms, 2 baths, a large screened Lanai with a heated pool and private backyard. The furnishings are more modern with a coastal vibe and the attached two car garage is large enough for all your toys. The primary bedroom offers queen sleeping accommodations and is En-suite. The second bedroom has a queen bed, with a twin trundle below, and the third bedroom has a full-size bunk bed with twin trundle and twin bunk bed. You will enjoy floating the day away in the heated pool, the back yard is fully fenced for Fido. Lovely, polished Terrazzo floors, fresh paint and coastal décor makes this a great place to spend your winter. You are about 6 miles from the world-renowned Siesta Key beach, a short drive to the newly refurbished Lido Beach and Pavilion, and the historic St. Armands Circle, like to kayak? Take a guided kayak tour through the mangrove tunnels or head to the new Legacy Trail for biking, walking running or rollerblading. For those rare rainy days, the UTC Mall offers many high-end shopping options and excellent Restaurants. Welcome to your dream vacation! ($150 cap on Utilities, guest pays to heat pool) Booked January 5th through March 2027.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)

Listing Agent: Stephanie Deshaies (941-780-3229)

Remarks: Welcome to the JefferSun House- a light & bright breath of fresh air & sunshine just minutes from world famous beaches & downtown Sarasota and located within the coveted Southside school district. This turnkey furnished 3 bedroom 2 bathroom heated pool home sleeps 8 & offers a private, fully fenced backyard w/ heated pool & BBQ grill. We are a dog friendly house, walkable to Arlington Park w/ its own dog park, walking trails & tennis courts. With a chef's kitchen & separate dining area you can bring the entire family & have the best of Sarasota at your fingertips. House can be rented unfurnished if desired.

Listing is courtesy of: UPTOP REAL ESTATE SERVICES, LLC (941-554-4896)

Listing Agent: Adam Kabinoff (941-554-4896)

Remarks: Adorable 2 Bedroom, 1 bath home featuring both a cozy living room and a separate family room.... Perfect for relaxing or entertaining. The interior and exterior have been freshly painted, giving the home a bright, updated feel. Enjoy a fully renovated kitchen, complete with brand new appliances. Washer and dryer hookup are available for your convenience, and lawn care is included for easy, stress-free living.

Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)

Listing Agent: Joe Martini (678-468-1340)

Remarks: This is a short term rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world-famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.

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

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

Remarks: Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely stroll from the vibrant Siesta Key Village (packed with shops, restaurants, and entertainment!) and a short walk to the world-famous Siesta Key Beach, consistently ranked #1 in the USA! From the moment you step inside, you'll be embraced by a cozy, comfortable atmosphere and tasteful coastal decor, instantly making you feel at home in your personal island paradise. The updated kitchen is fully equipped for making meals or entertaining, and the formal dining room offers serene views of the tropical backyard where you can dine al fresco or simply soak up the sun in this quiet, family-oriented haven. With a comfortable Queen bed in the primary, two Twin/Single beds in the second bedroom, and a versatile Daybed Sofa in the third, there's space for everyone. This is the tranquil, sun-kissed escape you've been longing for, a perfect place to create unforgettable memories – your Siesta Key adventure awaits!

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

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

Remarks: AVAILABLE JUNE 2026 for annual rental! Welcome to 4970 Reagen Way in beautiful Sarasota! This charming 3-bedroom, 2-bath single-family home offers comfort, space, and a welcoming neighborhood atmosphere — all tucked away on a quiet cul-de-sac. Step inside to find a bright and airy living room with vaulted ceilings, creating an open and inviting feel. The home features ceramic tile throughout with luxury vinyl flooring in the bedrooms — no carpet anywhere for easy maintenance. The primary suite includes a spacious walk-in closet, providing plenty of storage. Enjoy peace of mind with central A/C, a new roof (2023), and a whole-home water filtration system. The 1-car garage adds convenience, while the fully fenced backyard offers plenty of room to relax or entertain. You’ll love the LARGE screened-in lanai — perfect for enjoying Florida living year-round — as well as the expansive backyard complete with a fire pit and a large shed available for tenant use. Located in a well-maintained neighborhood with no HOA restrictions, this area is especially known for its festive holiday spirit — don’t miss the incredible Christmas light displays the community is famous for! Pets are welcome with owner approval, and there’s NO last month’s rent required, making move-in even easier. Don’t miss your chance to call this wonderful property home — schedule your showing today!

Listing is courtesy of: LEGACY REAL ESTATE ASSOCIATES, LLC (941-757-3588)

Listing Agent: Benjamin Bruce (941-713-5969)

Remarks: Discover this inviting home in Sarasota’s highly desirable Arlington Park neighborhood! This property offers comfort, style, and an unbeatable location. The open kitchen features an island, newer appliances, and flows effortlessly into the living area, creating a great space for everyday living and entertaining. The spacious primary suite includes a walk-in closet and private access to the rear deck. The en-suite bathroom offers a glass block walk-in shower and dual vanities. The guest bathroom has been tastefully updated with a custom rustic vanity. The third bedroom features a vaulted ceiling and access to a side deck—ideal for a flexible workspace or guest room. Bamboo laminate flooring runs throughout the home for a cohesive, modern look. Enjoy the outdoors in the large, fenced backyard with a wraparound deck. A new shed provides additional storage. You’re just minutes from Downtown Sarasota, St. Armands Circle, Siesta Key Beach (approximately 2 miles away), Sarasota Memorial Hospital, and a wide variety of shopping and dining options. Arlington Park offers fantastic amenities such as basketball courts, tennis courts, and a dog park. A fantastic opportunity in a prime location—schedule your showing today!

Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)

Listing Agent: Rebecca Krauss, Pllc (941-922-4959)

Remarks: Allow nature to welcome you to your private oasis on Lake Flamingo. Wake up drinking your morning coffee on the expansive deck enjoying the sunrise and bird watching on the spring fed lake. At the end of the day, enjoy grilling dinner on the expansive deck and sipping wine by the outdoor fire pit. This 3 bed, 2 bath home provides a split and open floor plan with water views from the entire rear of the home. Ample storage space throughout with 2 walk in closets, a 10 ft by 3 ft closet in the 3rd bedroom, a linen closet and a fair sized storage shed. Plenty of room on the side yard for a garden. Both the deck and back yard are fenced in. Very private. Nicely updated. Supermarket, restaurants, shops and pharmacy all 1-2 blocks away. Lease length is flexible.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Seth Westerberg (941-342-7653)

Remarks: Welcome to 3611 Bradenton Road in Sarasota! This 1936 Bayou Oaks charmer is brimming with character and modern comforts. Featuring 2 bedrooms and 2 bathrooms across 1,240 square feet, this home effortlessly blends vintage details with updated amenities. Step inside to enjoy a mix of classic wood, ceramic, and tile floors that flow throughout the space. The kitchen boasts solid wood cabinets, stone counters, and sleek stainless-steel appliances—perfect for whipping up your favorite meals. The spacious primary bedroom offers a walk-in closet, adding functionality to the home’s warm vibe. Outdoors, unwind on the expansive deck overlooking your private sanctuary, ideal for quiet mornings or hosting friends. Need extra space? The 26x12 workshop is a standout feature—it’s equipped with a refrigerator, microwave, AC, and screened porch, making it an excellent guest retreat or creative studio. There’s also an additional shed for all your storage needs. This pet-friendly property comes with central heating, air conditioning, and convenient on-site laundry access (washer and dryer included!). Situated just minutes from Downtown Sarasota, Ringling School of Art & Design, USF, New College, and beautiful beaches, you’ll enjoy easy access to shopping, dining, and outdoor fun. Tenant is responsible for lawn care in addition to rent at $180 monthly. Ready to experience the charm and convenience of this home firsthand? Schedule your showing today!

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

Listing Agent: Beth Harris (941-321-7148)

Remarks: Welcome home to this beautifully maintained residence offering comfort, convenience, and generous outdoor space! Property Features 3 bedrooms, 2 full bathrooms, 1-car attached garage, and a large fenced-in backyard. This thoughtfully designed home features a bright, open living area and a functional kitchen equipped with all major appliances, making move-in simple and stress-free. A full-size washer and dryer are included in the dedicated laundry room for added convenience. The comfortable primary suite includes a private bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Guest bath includes a soaker tub. Step outside to enjoy the large fenced-in backyard, perfect for entertaining, relaxing, or outdoor activities. The private yard adds valuable outdoor living space rarely found at this size. This home is ideal for individuals, couples, or small families seeking a well-maintained property with great indoor and outdoor living space. Contact us today to schedule a showing!

Listing is courtesy of: OSIPOV GROUP REAL ESTATE (941-284-4237)

Listing Agent: Bogdan Osipov (941-500-5885)

Remarks: #1-Rated Siesta Key Beach – AVAILABLE 1/10/26 Close to Sarasota Memorial & Downtown Cultural Scene***Discover the perfect blend of coastal living and city convenience! This beautifully updated Sarasota home is ideally located just minutes from Siesta Key’s world-famous beach, Sarasota Memorial Hospital, and the vibrant downtown arts district — offering easy access to dining, shopping, and entertainment.*** Property Highlights: Bright, open-concept living with abundant natural light* Modern kitchen with stainless appliances & granite countertops* Screened lanai for relaxing Florida evenings* Private fenced yard with tropical landscaping* Pet-friendly (with approval) ***Prime Sarasota Location: 10 minutes to Siesta Key – with #1 Beach in the USA* Close to Sarasota Memorial Hospital, Trader Joe’s, and Southside Village8 Easy access to Downtown Sarasota, St. Armands Circle, and cultural venues like the Van Wezel Performing Arts Hall. Come stay and you to0 will see, What's all the fuss about Sarasota!

Listing is courtesy of: FINE PROPERTIES (941-782-0000)

Listing Agent: Tracy Srodes (813-267-1312)

Remarks: Recently renovated home located at 1778 23rd St, Sarasota, featuring a fully updated interior and a new roof. The home offers a bright and functional layout with new finishes throughout and the convenience of an indoor washer and dryer area. The property is move-in ready and located close to shopping, schools, parks, and local Sarasota amenities. Housing vouchers are welcome.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: James Hogan (631-599-0728)

Remarks: Nicely updated 2-bedroom, 2-bath Home with a one-car garage in the beautiful Pinetree-Village Des Pins neighborhood might be just what you're looking for. It’s a single-story home with a great open layout and feels spacious without being overwhelming. This villa offers everything you need to feel right at home, including a brand new kitchen, a comfy living room, and a breezy screened lanai where you can kick back and take in the view, it’s the perfect spot to relax after a day of exploring. The community has some great perks, too – a beautiful heated pool, a hot tub, tennis courts, and a putting green if you want to practice your swing. There’s also a clubhouse with a game room and outdoor BBQ area. As for location, you couldn’t ask for a better spot. You’re just a short drive from Siesta Beach, TPC Prestancia Golf & Social Club if you’re a golf fan, not to mention, there are plenty of parks, museums, and cool spots to check out nearby.

Listing is courtesy of: CHARITY & WEISS INTERNATIONAL LLC (941-365-0022)

Listing Agent: Rudi Weiss (941-284-1013)