Remarks: Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary bedroom features a plush king-size bed and a bathroom across the way, providing a private sanctuary. Two additional bedrooms offer flexible sleeping arrangements: one with a comfortable king-size bed, and the other ideal for families with a double bed and a single bed. You'll find a full kitchen stocked with all the essentials, plus a convenient washer/dryer to make your stay effortless. Outside, your expansive, private backyard is a true highlight. Take a refreshing dip in the private heated pool, unwind in the bubbling hot tub, or simply lounge in the ample space for sunbathing and outdoor dining. With direct access to the intercoastal canal, you can enjoy quiet moments fishing or watching the tranquil tides. Leona's Retreat boasts a truly prime location on a quiet, family-oriented street. You're just a delightful five-minute stroll to the vibrant Siesta Key Village, brimming with charming shops, delectable restaurants, and lively entertainment. And for those iconic beach days, the world-famous Siesta Key Beach is only a ten-minute walk away! We've ensured you're perfectly equipped for a memorable day by the sea. The home includes all the beach day essentials: beach chairs, beach towels, coolers, frozen ice packs, and a convenient cart to easily tote everything down to the sand. Ready to experience the best of Siesta Key? Book your unforgettable stay at Leona's Retreat today!

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

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

Remarks: This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults upstairs. No need to fight over the king-size bed, as this home boasts two luxurious king-size bedrooms! Both offer comfortable retreats and easy access to your private pool, perfect for a refreshing dip anytime. The third bedroom features a trundle bed that comfortably sleeps two. Outside, the private pool area awaits with lounge chairs for sunbathing, an outdoor shower, and a delightful area to grill and enjoy alfresco dining at the table for six. Just moments away, the vibrant energy of Siesta Key Village, with its diverse culinary scene and local shops, offers endless opportunities for exploration. Surf's Up provides the ideal launchpad for experiencing all that Siesta Key has to offer, with plenty of room to relax and recharge in between adventures. Perfect for families seeking sun, relaxation, and easy access to Siesta Key Beach & Village. Book your unforgettable getaway now! 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: Take a look at this beautiful home, Clean and Move-In Ready, split plan featuring 4 bedrooms, 3 bathrooms, 2 car garage and approximately 2338 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated. Applications are First Come First Serve basis. Possible Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Christopher Yambo (813-458-9055)

Remarks: Beautifully updated 3-bedroom, 2-bath POOL home in desirable Seville at Center Gate! Available for an annual lease. Fantastic location just south of Bee Ridge near Publix, Home Depot and Walmart. Fully renovated with a stunning Italian-made kitchen and elegant Italian made tile flooring throughout, this home offers a sleek, modern feel with an open and inviting layout. The kitchen is a true centerpiece, featuring high-end finishes and quality craftsmanship—perfect for both everyday living and entertaining. Step outside to your private oasis! The spacious pool deck offers exceptional privacy with no rear neighbors and no neighbors on one side—ideal for enjoying the Florida sunshine year-round. Conveniently located near I-75, dining, shopping, grocery stores, and just minutes to downtown Sarasota. Pet Friendly! 1 small dog with $25 monthly pet fee. Pool maintenance and landscaping included. To be rented unfurnished but can be had furnished, let’s talk.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: John Trexler (941-320-8609)

Remarks: Available March 15th, 2026. Just two blocks to Siesta Drive and a few more to the bridge leading to Siesta Key! This immaculate mid-century Florida style home has wood flooring, an updated kitchen, 2 bedrooms, and a den. The large back yard is fenced for privacy and makes for a peaceful retreat. Located in Poinsettia Park, one of Sarasota's most desirable neighborhoods. Shopping, dining, beaches, downtown, and the hospital are all just a couple minutes away.

Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)

Listing Agent: Timothy Bloch (941-504-1111)

Remarks: Annual lease, NO PETS, Furniture included-Welcome to the sought-after Woodbrook community in this gated development with private access and resort-style amenities. Just a short walk from the community pool sits this charming traditional Florida home built by Neal Communities. Step inside to a bright, open floor plan with high ceilings and a spacious kitchen island perfect for morning coffee and family meals. The generous living room provides an ideal space for entertaining and gatherings. Outside, the backyard has been transformed into a private oasis with vinyl fencing, offering a safe play area for pets. The home backs to a natural preserve that stretches nearly 0.4 miles, delivering peaceful views and added privacy. Conveniently located, University Town Center is just a 10-minute drive, sandy beaches are approximately 25 minutes away, and downtown Sarasota or Bradenton are about 15 minutes. Easy I-75 access is only 7 minutes away. This is a wonderful opportunity in a prime location. Come see this lovely home today!

Listing is courtesy of: KONA REALTY (941-718-8293)

Listing Agent: Vlado Konatar (941-718-8293)

Remarks: GREAT LOCATION* Single Family Pool* UNFURNISHED Home* – Popular PALM AIRE* - 3 Bedrooms 2-1/2 bathrooms - Golf course and water views* from this inviting home in sought after Palm Aire. Spacious floor plan with most rooms having disappearing sliders to make the expansive lanai/pool part of your daily living space. Open living room and separate dining room with garden view - perfect for entertaining a large group. Eat-in kitchen with granite counters and custom back splash and a pass through to the lanai. Cozy dining area with slider opening onto the lanai. Family room has volume ceilings and wet bar. Open and airy master suite freshly painted with new vinyl flooring with his and her bath featuring dual sinks, and separate tub and shower. Two guest bedrooms with pergo flooring and shared bath. Oversize neutral tiles in main living areas. The HUGE caged lanai has an eastern exposure for optimum enjoyment of the pool, lake, and 3rd green/4th tee views of the Palm Aire golf course* Rent Includes: POOL MAINTENANCE, GROUNDS MAINTENANCE - MINUTES TO DOWNTOWN SARASOTA, ST. ARMANDS CIRCLE, LIDO BEACH & OTHER BEACHES ON THE GULF OF MEXICO, UTC MALL, i-75* EXCELLENT LOCATION*

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)

Listing Agent: Claudette Krijger (941-504-2081)

Remarks: Charming Sarasota Rental in Prime Location – Available Now! Welcome to 129 N Pompano Ave, a well-maintained and inviting residence ideally located in the heart of Sarasota. This charming home offers a perfect blend of comfort, convenience, and Florida lifestyle living. Featuring a spacious layout with abundant natural light, the property includes generously sized bedrooms, a functional kitchen with ample cabinetry, and comfortable living areas designed for both relaxation and entertaining. The home is thoughtfully maintained and ready for immediate occupancy. Enjoy the benefits of a private outdoor space, perfect for enjoying Sarasota’s beautiful weather year-round. The property also offers convenient parking and easy access to nearby amenities. Located just minutes from downtown Sarasota, world-renowned beaches, shopping, dining, and entertainment, this home provides unmatched accessibility. Quick access to major roadways makes commuting a breeze. Highlights: • Prime Sarasota location • Spacious and bright interior • Private outdoor area • Close to beaches, downtown, and shopping • Ready for immediate move-in Don’t miss this opportunity to live in one of Sarasota’s most desirable areas. Schedule your showing today!

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

Listing Agent: Mike Sorensen (941-380-2900)

Remarks: This one-bedroom, one-bath furnished rental guest house is recently renovated with private entrance, fenced patio/yard area, your own free- standing HOT TUB and access to the shared POOL in the back yard! There is a stackable PRIVATE LAUNDRY conveniently located in the walk-in closet to the bedroom. The kitchenette boasts a large granite countertop with induction cooktop, refrigerator, small convection oven, icemaker, and is open to the living room that has a sofa-bed. The fold-down table can be used as a desk or pulled out from the wall to seat 4. There is one shared wall in the guest house. The location is close to SMH and Southside Village restaurants and shops. Minutes from Bayfront Park, Selby Botanical Gardens, Marina Jacks, St. Armand's/Lido Key, and Siesta Key. Great Neighborhood! November-December $2000/month, Jan-April $3,000/month, May-October $2000/month. Inquire for shorter or longer stays.

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Kari Klein (941-961-7419)

Remarks: AVAILABLE JAN & APR 2027. Welcome to The Hamptons on Palmer Ranch! Your vacation single family 3/2 pool home awaits you. As you enter through the double entry front doors, you are led into the bright and spacious great room, custom kitchen with granite counters and cherry wood cabinets, a large breakfast bar, and opens to the dining area, making it perfect for both everyday living and entertaining guests. Spacious master suite features a sitting area, sliding glass doors opening onto the lanai, large walk-in closet, King size bed, en-suite bathroom with dual vanities, soaking tub and separate walk-in shower. The 2 guest bedrooms have laminate wood flooring and a queen bed, guest bathroom with a single vanity and tub/shower combo. From the spacious great room, you walk out of the large sliding glass doors to the serene views of the heated sparkling pool & peaceful pond and preserve views, and lush landscape surrounding the property. Relax or dine outside on the covered lanai and enjoy the beautiful sunsets. The Hamptons is located in the heart of Palmer Ranch and just a short drive to Siesta Key beach, shopping, restaurants, parks, and close access to Downtown Sarasota, and Legacy Walk/Bike Trail. Quick access to I-75. Sorry, no pets allowed.

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

Listing Agent: Chrissie Cummings (772-532-8229)

Remarks: Siesta Key Annual rental. Located just a half mile from Siesta Key Beach, this four-bedroom, two-bath home is tucked away in the quiet Hidden Harbor area. Set in a beautiful tropical environment with canopy-lined streets, the property features 2,300 square feet of living space and a 1200-square-foot lanai. The interior offers an open floor plan with vaulted ceilings, skylights, and updated kitchen and baths. Each bedroom includes a private balcony with shelving in each closet. The master bathroom features a soaking tub, shower, and a double vanity with marble counters. Sliding doors from the living room and kitchen/family room open to a large screened-in lanai and a two-story deck. Outside, you will find a pristine, caged, heated swimming pool with waterfall and spa - perfect for entertaining. The home is situated on an oversized lot with a gated entrance. It offers two zone air-conditioning and heating units. The home has a metal roof and hurricane impact windows and has a 2-car detached garage. Enjoy the island life with proximity to the Gulf of Mexico and the boutiques, restaurants, and nightlife of Siesta Key Village. Rent includes weed control, leaf pickup, pool maintenance, pest control, and internet. The fireplace is not for tenant use.

Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)

Listing Agent: Margaret Young (941-359-3435)

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: Located in the desirable community of Promenade Estates in Palmer Ranch, this gorgeous UNFURNISHED 4 bedroom, 3.5 bath, 3 car garage is where you want to call home! Conveniently located 1 mile from The Legacy Trail, Publix, Lowes, & Target. Pine View School is also just 7 min. away! This home has tons of features including a pool, heated spa, granite countertops, stainless steel appliances, crown molding, a dry bar with a beverage cooler, and recessed lighting. With almost 4,000 square feet, this large home is the perfect blend of work hard, play hard. Upon entry you are greeted with the beautiful staircase and off to the right is an office space with great natural lighting and a half bath for convenience. To the left is access to the 3 car garage and an over sized laundry room with built in details such as a folding counter, wardrobe rods, a mud room bench & plenty of cabinet space. Continuing through the entry way will bring you into the kitchen, dining room, & living room. This open floor plan is perfect for family time! The master bedroom is off of the kitchen/dining room featuring tray ceilings and an ensuite bathroom with a soaking tub as well as a walk in shower, a double sink vanity & a walk-in closet. Upstairs you will walk into another family room/den with some extra space for a desk. The second floor has 3 bedrooms & 2 bathrooms. Outdoor features include lush landscaping, a pool, a heated spa, and a lake view perfect for your morning cup of coffee! Community amenities include a resort style pool, a fitness center, a splash pad, playground, basketball court and a volleyball court. Nearby is a variety of restaurants, shopping and about a 15 minute drive to beaches. Pets may be considered upon owner's discretion, no restrictive breeds. Lawn care & pool maintenance will be included in the rent. Please note HOA requires a minimum of 7 months. Call now for more details!

Listing is courtesy of: ROSSI & COMPANY INC (941-955-7368)

Listing Agent: Deserea Hardy (941-960-6480)

Remarks: Charming 3-Bedroom Home with Modern Upgrades and Bay Views. Welcome to 8185 Long Bay Blvd, a beautifully renovated home located in the heart of Sarasota. This home is seconds to the stunning Sarasota Bay, so enjoy water views every time you drive home. This character-filled house, originally built in 1952, was completely rebuilt in 2017, offering the perfect blend of historic charm and modern amenities. This 3 bed 2 bath home offers a spacious, open floor plan. It is a split plan with the master ensuite very private on the north side of the home and the 2 other bedrooms with a shared contemporary bathroom on the south end. The open floor plan allows lots of natural light and the home has tile throughout. The home is located on a generous corner lot appx .38 acres with a U shaped driveway welcomes your guests. The back yard is ample, fully fenced and perfect for pets with lots of shade. Pet friendly owner with a REFUNDABLE PET DEPOSIT of $500 pending no damages. This home is perfect for those seeking a move-in ready property with all the modern conveniences. Enjoy the serene surroundings and the vibrant Sarasota lifestyle, with nearby parks, shopping, dining, and cultural attractions. Don’t miss the opportunity to make this beautiful house your new home. Contact us today to schedule a viewing!

Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)

Listing Agent: Alyssa Cromie (941-928-7288)

Remarks: This very well cared for one story 3 bedroom 2 bath home is in an excellent Sarasota location. Close to all major shopping, restaurants and grocery stores. Located next to Red Bug Slough, a 72 acre preserve that has has several miles of hiking trails, a small playground, picnic shelters and a fishing dock. This property is less than 7 miles to Siesta Key beach. This home is an open floor plan with an updated kitchen with newer appliances and updated bathrooms and brand new interior paint. There is a huge Florida room at the back of the home that is 35 feet wide and is open to the living areas. The one car garage is deep and will fit a vehicle with room to spare in front. The lawn and landscape maintenance is taken care of for you. Pets are possibly and approved on a case by case basis.

Listing is courtesy of: REALTY BY DESIGN LLC (941-779-4509)

Listing Agent: Brian Odonnell (941-779-4509)

Remarks: Lovely single family home in Ridgewood available for a short term rental. This light and bright two bedroom two bathroom turnkey furnished single family home has a lots of appeal. Open kitchen/living room/dining room combination, terrazzo floors throughout, lots of windows and one car attached garage. The kitchen has stainless appliances, lots of counter space and cabinets, closet pantry and a kitchen island with seating. Primary bedroom has a king sized bed. The guest bedroom has a queen sized bed. Bonus room off the living room can be used as an office. First bathroom has a tub/shower combination and the second bathroom has a stall shower. The home has a very large, fully fenced yard. Perfect for a dog. The owner will consider a small to large sized dog with a non refundable $300 pet fee. SEASONAL RENTAL AND WIDE OPEN FOR 2026 summer and fall. Rent for December through April is $3,500 monthly. Rent for May through November is $2,350 monthly. This will not last long so call today!!

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

Listing Agent: C. Alison Hunter (941-587-5667)

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)