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: Looking for the absolute PERFECT beach vacation location?? Well, look no further, this one has it all!! Walk or bike to absolutely everything Siesta Key has to offer! Restaurants, shopping, public beach access, and incredible sunset views are all nearby! Take a stroll and enjoy the sights or hop on one of the bikes that have been provided by the owner and hit the white-sand beach! This is Florida living at its absolute finest!! All utilities (Electric, Water, Hi-Speed Internet, Cable, and Trash Service), pest control, and landscaping are included in the rent! So, enjoy your stay MAINTENANCE FREE!! This wonderfully renovated FULLY FURNISHED 3-bedroom, 2-bath single-family home has more than enough space to accommodate a large group. Enjoy dinner and wine on the rear patio or take a short stroll to some nearby hot spots! You are minutes away from one of the most highly rated beaches in the country, Siesta Key Beach! Walk or take one of the owner provided bikes to explore SIESTA KEY BEACH and all of the local beach-front attractions. The home is fully furnished and turnkey ready! It’s stocked with cookware, utensils, linens, and everything you need for a short stay or an annual lease! This home features: Paver driveway with Covered parking, fully fenced backyard, new roof, remodeled kitchen, stainless steel appliances, granite countertops, clothes washer & dryer, storage shed, and so much more. Known for its stunning white sandy beaches, warm climate, and vibrant arts and culture scene, live like you are on vacation! Clear turquoise waters and soft white sand, Sarasota is home to some of the most beautiful beaches in the world! Siesta Key Beach, Lido Beach, and Longboat Key Beach are all top-rated destinations for swimming, sunbathing, fishing, boating, and watersports. Beyond the beaches, Sarasota is home to a thriving arts and culture scene. The city is home to the Ringling Museum of Art, which boasts an impressive collection of European paintings, as well as the Sarasota Opera, the Sarasota Ballet, and the Asolo Repertory Theatre. The downtown area of Sarasota is home to numerous art galleries, studios, and theaters, making it a hub for creativity and innovation. Easy access to interstate 75, airports, shopping, restaurants, nightlife, and more!! Now is the time to make the move – come enjoy Florida lifestyle at its finest!! Off-Season Rates: (May 1 – December 31) = $3,650/month + tax In-Season Rates: (January 1 – April 30) = $6,000/month + tax 30-Day minimum rental required. Tenant pays a 1-time move-out cleaning fee of $350. Taxes (13%) are paid by Tenant on any lease 6 months or LESS in duration. CURRENT AVAILABILITY: 2026: SEPTEMBER, OCTOBER, NOVEMBER, DECEMBER 2027: JANUARY, FEBRUARY, MARCH, APRIL, MAY, JUNE, JULY, AUGUST, SEPTEMBER, OCTOBER, NOVEMBER, DECEMBER

Listing is courtesy of: NETWORK REAL ESTATE GROUP (941-803-0344)

Listing Agent: Shawn Peacher (703-405-2615)

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: Available as a monthly rental in May, August, September, October, November and December 2026 only! Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock, watching for playful manatees and jumping fish, or simply basking in the sunshine by your private pool. With ample outdoor space for lounging, dining, or even trying your hand at fishing, this backyard oasis is your personal paradise. Inside, the home offers a beautifully appointed, light-filled space. The primary bedroom boasts a comfortable King bed and an en-suite bathroom, while the second bedroom features a Queen bed, and the third provides flexible sleeping with two Twin/Single beds. The fully equipped kitchen is ready for family dinners, though with the vibrant Siesta Key Village near, you might prefer to explore the array of locally owned restaurants, cafes, and lively bars. The unbeatable location means you're not only steps from delicious dining and entertainment, but also just a short 3-minute drive (or a fun bike/golf cart ride, a local favorite!) to the world-famous Siesta Key Beach, consistently ranked among the best in the USA. Please note: If you are bringing a pet, there is a $250 pet fee (per pet). We encourage you to inquire about the specific pet policy applicable to your reservation for clarification, including how and when the pet fee will be collected.

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

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

Remarks: Beautiful home in lovely gated community in Palmer Ranch. All amenities. Perfect location close to shopping, medical, the Legacy Trail, fabulous beaches, within minutes. Great Schools. Immediate availability.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)

Listing Agent: Lorraine Neal (941-350-0997)

Remarks: This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full bath, with its only living room are located on the ground floor with private patios front and back. Think in-law suite. In addition an office/bonus/exercise room is located on the ground floor. The third floor host a loft with a full bath and entertainment area. A full wrap around deck covers the back of the home. The master and guest have a private deck as well. 2 car garage with built in storage. Additional parking left and right side of driveway. House comes fully furnished. 8 month min. lease, available today.

Listing is courtesy of: STARLINK REALTY INC (239-693-7263)

Listing Agent: Christopher Davenport (678-776-2617)

Remarks: Palmer Ranch 6 month rental. Rented January - May 2027. Palmer Oaks, a gated community at the edge of South Sarasota's Palmer Ranch - close to I-75 and 5 miles to the white sands of Siesta Key beach. Built in 2011 by D R Horton, this three bedroom/two bath/two car garage home overlooks a pond and fountain. Spacious living room/dining room with new Luxury vinyl plank flooring as you walk through the front door. New upgrades such as LVP flooring in the living/dining room and a large custom closet in the Master bedroom. Relax and entertain in the combined family room and kitchen area with 18” ceramic tile floors, maple wood cabinets, granite countertops, stone backsplash and center island. Both bathrooms have granite countertops and there are dual sinks in the master bath. Two additional bedrooms and the lanai overlooking the pond create plenty of living space. Full size washer and dryer. The heated community pool is located nearby. Palmer Oaks is a maintenance free community conveniently located close to shopping, restaurants, markets, I-75, the Legacy Biking Trail and the world-famous Siesta Key Beach. This beautiful home is the perfect location for your Florida get a way. Available now for 6 months or longer. Tenant to pay utilities on a 6 month + lease.

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

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

Remarks: This is one of those special properties that only comes on the Rental market once in awhile. This immaculate 3BR/3BA private home is situated on 1/2 acre - completely private. The third bedroom can be an office with a built in desk or en suite. This spectacular home features: updated gorgeous kitchen, amazing wood and slate flooring, updated appliances, sitting bar, dining area, open floor plan, indoor laundry (washer/dryer included), and stunning open beam ceiling. The master suite is private and has built ins and a fantastic bathroom. The other bathrooms are all beautifully updated with granite and slate as well. Oversized large lanai area with an above ground spa. The grounds are maintained by the Landlord. This is truly a special home. The owner is looking for a long term quiet tenants. There is a full credit, background, employment, and civil check on all tenants.

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

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

Remarks: Welcome HOME to this charming SARASOTA Florida Bungalow Getaway. FURNISHED RENTAL. This well furnished 2BR + guest suite /2BA home. Relax and enjoy the spacious screened Lanai in the outdoor living room and the privacy of the fenced backyard. Great location with easy access to Downtown SARASOTA restaurants, theaters, and shops. Just a few minutes and you are on SIESTA KEY or LIDO KEY beaches. Walk a half-mile to ARLINGTON PARK to enjoy activities suited for the whole family. This city park features two pools, a gymnasium, athletic courts, and a playground. Located on a peaceful street, this beautifully updated home affords a prime central SARASOTA location. Spend a sun-soaked at the beaches on SIESTA KEY or LIDO KEY, or simply unwind in your spacious lanai. This is a short term rental and can be rented for two months or longer based upon availability. Monthly Rates for December through April $4500. May through November $2650. Additional charges are monthly cleaning fee $200 and utility overages above the monthly electric cap $150. Sales and Resort Taxes (13%). OPEN for 2027 Season Reservation $4,500 month.

Listing is courtesy of: WAGNER REALTY (941-955-1500)

Listing Agent: Patrice Ivan (941-993-0823)

Remarks: Seasonal/short term turnkey furnished home. Spacious beautifully renovated single family home in quiet convenient neighborhood on a cul-de-sac downtown Sarasota. This home is flooded with natural light from abundant windows and has a vaulted ceiling to enhance the open planned design. The open floor plan makes family time and entertaining easy with a den and living room. The furniture is new and stylish with comfort in mind. The kitchen boasts solid wooden cabinetry topped with slab granite counters with breakfast bar, stainless steel appliances, built in desk, eat in space in the kitchen and pantry. The primary bedroom is very large with a king bed, door to lanai, en suite bathroom with dual vanities, soaker tub, separate shower and roomy walk in closet. The other bedrooms are split plan and there is also a private office. The laundry room has full sized machines, utility sink and loads of cabinetry for extra storage. The two car garage has an epoxy floor and is immaculate just like the house. Want to enjoy outdoor entertaining yet keep the bugs away-you can with a large screened in lanai with covered seating as well. This home is well located and convenient to shopping, casual and fine dining, excellent schools, downtown Sarasota with theater, opera and museums and only 10 minutes to Siesta Key, the number one beach in the country. This home is now rented Jan thru March 2026. Call today to lock in your time in the sun!!

Listing is courtesy of: RENT SARASOTA (941-328-8999)

Listing Agent: Hamid Mohajir (941-557-8556)

Remarks: Seasonal/short term only Want to come to the Florida sunshine and be close to all the action but feel like you are in the middle of a nature preserve? This warm and welcoming home is for you. This home is spacious and natural light filled from high ceilings, clerestory windows. This house has interesting architectural detailing and is comfortably furnished for your pleasure. The kitchen is large with an eat in space, pass thru to dining room, custom tile backsplash, pantry and stainless steel appliances. The living/ dining/ main bedrooms all have wonderful views of the pool, lake and preserve. I actually saw a bald eagle in the tree behind this home waiting for lunch in the lake beyond! The pool is large, heated and has a covered and screened entertaining area. Convenience is key here-this home is close to shopping and dining, not far from I-75 or the airport, downtown Sarasota and the beach. This home is now rented thru March 2026. CALL TODAY to sign up for your time in paradise! High season (December thru April) are $7000/month + 13% tax and off season (rest to the year) is $2995/month + tax. This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details.

Listing is courtesy of: RENT SARASOTA (941-328-8999)

Listing Agent: Hamid Mohajir (941-557-8556)

Remarks: Welcome to Hillview Digs! Hillview Digs is a fully furnished two story Farmhouse moved from downtown Sarasota in the mid fifties . Just shy of 2000 square feet and equipped with 3 bedrooms, 2.5 bathrooms, an office area, a family room/den separate from the main living room. For your convenience, the master bedroom is on the first floor with the other 2 bedrooms upstairs. This cozy home features tasteful decor, comfortable hang out spots such as a sitting room, a den with a smart TV and coffee bar and a beautiful spacious outdoor deck. The outdoor deck has ample seating for lounging or entertaining, a gas grill and umbrella for shade. There is one covered parking space as well as an oversized driveway for additional parking. Located in Arlington Park, this beautiful home is close to downtown Sarasota and 6 miles from Siesta Key Beach. Owner may consider a pet upon their discretion and with non-refundable pet fee, NO RESTRICTIVE BREEDS. Available May 2026, call now for more details!

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

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

Remarks: Move in special! First month only $1,000! Welcome to a fresh home with stunning surroundings in beautiful Sarasota, Florida. Look no further than this gorgeous 3 bedroom, 2 bath, 2 car garage home located in subdivision complete with a park & walking trails. With plenty of space for your family and all the modern amenities you need to feel right at home, this home is sure to impress. From the spacious bedrooms to the gorgeous kitchen with new fridge and open living areas, this place is perfect for anyone looking for a comfortable and convenient home with short drive to stores and beaches. Laundry equipped with a new washer & dryer! All windows have custom blinds installed for your convenience! Refrigerator and stove included. So why wait? Contact today to schedule your visit on this beautiful home available for you.

Listing is courtesy of: PREMIER PROPERTIES OF SRQ LLC (941-526-3113)

Listing Agent: Yevgeniy Vla Salyuk (971-255-2669)

Remarks: Unfurnished, gorgeous and cozy Sarasota home, conveniently located near beaches, downtown, airport, and more. Welcome to your 3-bedroom annual rental home, exactly the perfect-sized home you have been waiting for to call your own. Meticulously cared for and move-in ready home, complete with large living spaces, high ceilings and wide fans for cool summer days indoors. Plus a stylish lux kitchen and accessible dining space that welcomes family and friends alike. Split floor plan, with plenty of bedroom space and privacy. A peaceful master bathroom, plus a shared bathroom for bedrooms 2 and 3. Glide out the sliders and find an oversized and tucked in screened lanai for indoor and outdoor living, plus a large fenced backyard, and covered canopy for shade!! Great storage shed tucked to the side out back for your convenience and storing seasonal belongings or other outdoor storage. 2 car garage spaces and this rental includes the washer, dryer, plus extra fridge. Yard cared for by the owner's yard service. Don’t delay, this sunny home is exactly what you’ve been waiting for.

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

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

Remarks: $2,775 a month May - December $3500 January-April . One month, seasonal and long term rentals accepted. Call for rates and availability Come down to Sarasota, Florida, one of the best places in the US to enjoy the warmest waters, beautiful beaches, stunning sunsets, delicious food, and world-class entertainment! We are pleased to list this newly renovated, bright three-bedroom, two-bathroom rental home nestled in a safe and family-friendly neighborhood in central Sarasota. You will be just a short drive away from local beaches, dining, shopping, entertainment, golf courses, and grocery stores. The home features modern appliances, new mattresses, a washer and dryer, new A/C, and high-speed internet. You’ll find everything you need for a comfortable stay, including a one-car garage for the peace of mind of knowing your vehicle is secure. You can also relax in the beautiful lanai area to enjoy the outdoors in the shade. For those who enjoy an active lifestyle, our property borders the famous Legacy Trail, which is perfect for regular exercise, whether you prefer biking, running, or walking.

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)

Remarks: Beautifully updated single-family home available for rent in one of Sarasota's most sought-after locations — just minutes from world-famous Siesta Key Beach, downtown Sarasota's dining and arts scene, and top-rated schools. No HOA restrictions. No CDD fees. Just a turnkey home ready for you to move right in. This thoughtfully designed residence offers flexible living for a wide range of lifestyles. The main home provides bright, comfortable living spaces anchored by a modern electric fireplace, while a private in-law suite with its own full kitchen gives you options — whether you need space for family members, a long-term guest, a home office, or a creative studio. Every major system has been recently updated, so you can move in with total confidence: new roof (2023), HVAC (2021), new flooring (2023), remodeled bathrooms, new windows (2024), new front door (2025), updated landscaping, and all-new appliances. Smart-home features including a Google Nest thermostat and Ring security cameras are already in place for your comfort and peace of mind. The fully fenced private lot offers a quiet retreat to relax and entertain — rare for a rental in this price range. Furniture and select equipment may be included for qualifying tenants, making this one of the most seamless move-in opportunities on the market. Available now. No HOA. No CDD. Pets considered on a case-by-case basis.

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: Rian Kelly (941-780-3890)

Remarks: Turnkey furnished single family home in the Meadows is available to rent. The large home has three bedrooms, two bathrooms, split bedrooms, and a living room/dining room combination. The kitchen has stainless appliances and a breakfast nook. The primary bedroom has a queen sized bed, two big closets and an en suite bathroom with double sinks, garden tub, stall shower and a linen closet. The first guest bedroom has two twin beds and the second guest bedroom is set up as an office with a pull out sofa bed. The guest bathroom has a tub/shower combination. The home has a caged lanai with heated pool, several sitting areas and lush landscape view of a golf course. The home has a laundry room, two car garage and is located on a very quiet cul-de-sac. Available January 15, 2026 for an annual rental or short term rental. Long term rental rate is $3,000. Short term, two month or longer, rate is $6,500 monthly plus state/local tax, booking fee and damage deposit. Located in the Meadows which is home to the Meadows Country Club that offers seasonal, social and full memberships, three golf courses, club house and tennis courts (home does not come with a country club membership but guest/tenant may sign up for one themselves.) No trucks allowed unless it can be parked in the closed garage due to the Meadows community rules. Close to Nathan Benderson Park, University Town Center, Sarasota/Bradenton Airport, I75 highway, University Parkway, shopping, grocery stores, coffee shops and much much more.

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

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

Remarks: Charming Lido Shores beach cottage steps from residents’ private gated white sand beaches and crystal blue waters of the Gulf of Mexico. Lido Shores is renowned for many Sarasota School of Architecture masterpieces and waterfront estates. Westway Drive is home to some of the city's most fashionable and expensive properties. This 3/3 furnished home (with many signature pieces from "The Sarasota Collection Home Store") is Canopied by a lush mango tree, with a tranquil and tropical setting. Enjoy the spacious backyard and a large 400+ sq ft screened-in front lanai that’s ideal for morning yoga and even better for evening cocktails. From the bright entry is a spacious dining room with an open-concept kitchen with countertop space and seating. Beyond the kitchen, is a spacious open dining and living area. The bedrooms are thoughtfully laid out to preserve privacy and ensure plenty of room with private baths. The largest suite has a queen bed, and a dedicated office with a comfy chair & TV. The front bedroom has a king bed and welcomes light from a set of French doors that open directly to the screened Lanai. The third bedroom has a queen bed and access to the guest bath. This stylish home is located in the heart of Lido Shores. St. Armands Circle is located less than a mile away, providing world-class shopping and dining.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-957-3730)

Listing Agent: Valarie Wadsworth (941-780-3858)

Remarks: Welcome to your perfect Sunset Splash! Professionally managed by Gulf Coast Vacation Rentals. This beautiful 3-bedroom, 2-bathroom private pool home offers the ideal blend of comfort, relaxation, and coastal charm—all just a short drive from the world-renowned white sands of Siesta Key Beach, vibrant downtown Sarasota, and top attractions like St. Armands Circle, The Ringling Museum, and the Marie Selby Botanical Gardens. Upon entry, you'll be welcomed into a light and airy open-concept space designed for easy living. The spacious living room invites you to unwind after a day of exploring the Gulf Coast, with plenty of comfortable seating and a large TV for entertainment. The kitchen is a chef’s delight, featuring stainless steel appliances, expansive countertops, and three barstools perfect for casual meals or morning coffee. Just adjacent, the dining table seats up to six, making it the perfect spot for family dinners or game night. Slide open the glass doors to reveal your private outdoor oasis. Enjoy the Florida sunshine lounging beside the large free-form pool, or dine alfresco at the outdoor dining table while surrounded by lush tropical landscaping. The primary bedroom is a spacious retreat with a king-size bed and an additional twin-size bed, ideal for families or extra guests. It also features an en-suite bathroom with a large vanity and a walk-in shower. The second bedroom includes a cozy queen-size bed and plenty of room to relax, while the third bedroom also offers a queen-size bed with inviting décor. The second bathroom is thoughtfully designed with a large vanity and a shower/tub combo to accommodate guests with ease. Whether you're soaking up the sun poolside, exploring Sarasota’s vibrant arts and dining scene, or enjoying a beach day on the Gulf, this home offers the perfect base for your Florida vacation. House Rule: No smoking. No burning candles inside of lodging. No parties. Not Pets.  THERE IS NO POOL HEATER.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Andy Moore (941-877-5588)