Location: Sarasota
Do Not Show Listings
4535 LONGWATER CHASE #18, SARASOTA, FL 34235
$1,7907 Days on yellowkey MLS ID: A4699443
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1108 Built: 1979Community: Longwater ChaseCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Gocio Elementary
High School: Booker High
Tax Year:
Middle School: Booker Middle
Remarks: BEAUTIFUL AND SPACIOUS CONDO 2BED/2BATH IN THE MEADOWS / 2ND FLOOR-- WITH A GORGEOUS GOLF, LAKE VIEW / FURNISHED / AVAILABLE FOR ANNUAL LEASE. *2 CLOSETS IN MASTER-BEDROOM / WASHER & DRYER-WALKING LAUNDRY ROOM / LANAI / ASSIGNED CARPORT PARKING+GUEST PARKING / BASIC CABLE-TV-INTERNET INCLUDED.---------------- 2 COMMUNITY POOL HEATED FOR ONLY RESIDENTS OF LONGWATER CH. \ PLAYGROUND & BASKETBALL COURT. OPTIONAL MEMBERSHIPS PROVIDE ACCESS TO AN INCREDIBLE AMENIT LIFESTYLE INCLUDING: 15 Har-Tru tennis courts • 10 pickleball courts • Championship golf • Junior Olympic swimming pool • State-of-the-art fitness center TENNIS COURTS, 15 MILES OF WALKING AND BIKING PATHS, 80 LAKES, AND 3,400 HOMES (CONSISTING OF CONDOMINIUMS AND HOUSES) UNIQUELY PLACED WITH BEAUTIFUL VIEWS OF THE LAKES, GOLF COURSES, AND AWESOME SPANISH MOSS CLAD OAK TREES, MATURE LANDSCAPING, & LESS THAN 20 MINUTES TO BEACHES, DOWNTOWN, AND ST ARMANDS CIRCLE. LESS THAN 5 MINUTS TO THE MALL "UNIVERSITY TOWN CENTER"--------------------- NO PETS / NO TRUCKS / NO SMOKING.-----------------ONLY AVAILABLE FOR LONG TERM.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Cecilia Fernandez (941-400-7075)
4378 MADERIA COURT CT #n/a, SARASOTA, FL 34233
$2,5002510 Days on yellowkey MLS ID: A4446120
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1988 Tax: $1,772 (2021)Community: Casa Del SolCondo
Taxes:$1,772
Elementary School: None
High School: None
Tax Year: 2021
Middle School: None
Remarks: AVAILABLEL FOR 2027 SEASON! CENTER GATE AREA CONDO! Second floor 2/2 condo overlooking a pond with a screened lanai. Vaulted ceiling give this condo a bright spacious feeling. Eat in Kitchen and a dinning room, washer and dryer included. Walking distance to the pool, tennis, shuffle board and clubhouse with fitness room. This is not available annually. THREE MONTH MINIMUM.
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Robin De Busk (941-922-4959)
2220 BAHIA VISTA ST #G4, SARASOTA, FL 34239
$1,75015 Days on yellowkey MLS ID: A4699985
REDUCED by $50 (2.8%) on 07/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1024 Built: 1980Community: Cordova Gardens IiiCondo
Elementary School: Alta Vista Elementary
High School: Sarasota High
Remarks: Welcome to your own private retreat in the heart of Sarasota. Tucked away at the quiet rear of the highly desirable Cordova Gardens community, this bright ground-floor residence offers an uncommon blend of privacy, natural beauty, and exceptional convenience. Surrounded by mature tropical landscaping, the home feels peaceful and secluded, yet places you just minutes from Downtown Sarasota, Bayfront Park, the John Ringling Causeway, St. Armands Circle, Lido Key, and the world-famous white sands of Siesta Key Beach. Inside, five sliding glass doors bathe the home in natural light, creating an open, airy atmosphere that feels welcoming from the moment you enter. The seamless connection between the interior and the lush greenery outside brings a sense of calm that is increasingly rare in such a central location. Positioned on the ground floor with no stairs to climb, this home offers both comfort and convenience. Cordova Gardens is a quiet, beautifully maintained community known for its park-like setting, towering shade trees, and sparkling community pool. Whether enjoying a morning walk beneath the mature canopy or relaxing poolside on a sunny afternoon, residents appreciate the peaceful lifestyle this hidden gem provides. The location is difficult to match. Sarasota Memorial Hospital is nearly adjacent to the community, making this an exceptional choice for healthcare professionals and anyone seeking an easy commute. Sarasota High School is directly across the street, while Southside Village, Publix, Trader Joe's, Whole Foods, Sprouts Farmers Market, Payne Park, Marie Selby Botanical Gardens, the Legacy Trail, and countless restaurants, coffee shops, boutiques, and entertainment venues are all just minutes away. With easy access to US-41 and I-75, the very best of Sarasota is always within reach. If you've been searching for a bright, private, ground-floor home in a quiet community with mature landscaping, a community pool, and an unbeatable Sarasota location close to downtown, Sarasota Memorial Hospital, waterfront parks, shopping, dining, and the Gulf beaches, this exceptional residence is ready to welcome you home. Tenant responsible for utilities. Must have renters liability insurance.
Listing is courtesy of: BLUE SKY REAL ESTATE (941-587-3492)
Listing Agent: John Werner (941-587-4579)
39 S POLK DR, SARASOTA, FL 34236
$29,4302592 Days on yellowkey MLS ID: A4438333
REDUCED by $3,420 (10.4%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2572 Built: 1951 Tax: $23,216 (2021)Community: Lido Beach Div BSpa: YesSingle Family
Taxes:$23,216
Remarks: Booked July 18-25th, August 3rd-6th, Aug. 31st-Nov. 14th, Nov 25th-Dec. 12th, Dec. 26th 2026-Jan 3rd, Feb. 12th-April 10th, June 19th-July 3rd, July 24th-31st, Aug. 28th-Nov 20th, Dec. 25th 2027-Jan 2nd 2028. Welcome to your private slice of paradise on Lido Key. Perfectly positioned on a wide canal with direct access to Sarasota Bay and the Gulf, this beautifully renovated coastal retreat combines luxury, comfort, and an unbeatable location just a short walk from St. Armands Circle and Lido Beach. The heart of the home is the stunning chef's kitchen, featuring quartz countertops, custom cabinetry, stainless steel appliances, a gas cooktop, and a spacious island with seating—perfect for gathering with family and friends. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, creating an inviting space for entertaining. Step outside to your private resort-style backyard oasis. Lounge beside the heated pool and spa, enjoy meals at the outdoor dining table, grill your fresh catch on the BBQ, or relax in the covered outdoor living room complete with comfortable seating and a TV. Surrounded by lush tropical landscaping, the backyard offers exceptional privacy and a true Florida resort experience. The private dock sits on a wide canal and is ideal for fishing, paddleboarding, kayaking, or docking a rental boat. After a day on the water or at nearby Lido Beach, stroll to St. Armands Circle for world-class dining, shopping, and entertainment before returning home to unwind beneath the stars. The home includes Smart TVs, board games, bicycles, beach chairs, umbrellas, toys, a cooler, and a beach wagon to make your walk to the beach effortless. Families traveling with little ones will appreciate the included pack-and-play and high chair. This property can be rented as a 4-bedroom, 4-bath retreat sleeping up to 8 guests, including the private guest house with its own full kitchen, living room, and washer/dryer. The main house has 3 bedrooms and 3 baths. When rented with guest house (an extra charge), it becomes a 4 bedroom and 4 bath rental. The $29,430 is for base rent only. There are taxes, an insurance fee, cleaning fees, and pool heating fee. City of Sarasota Certificate VR22-00088
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
4653 HADFIELD DR, SARASOTA, FL 34235
$15,000716 Days on yellowkey MLS ID: A4619916
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3674 Built: 1993Community: The HighlandsSpa: YesSingle Family
Remarks: Booked October 15th-December 27th 2026, Jan. 6th-March 28th 2027 Welcome to your private golf retreat in The Highlands, one of the area's most sought-after golf course communities. This beautifully appointed 4-bedroom, 4.5-bath home offers spacious accommodations, exceptional privacy, and all the comforts needed for an unforgettable vacation. Designed with both relaxation and entertaining in mind, the home's expansive floor plan features a private three-bedroom guest wing that can be closed off from the main living areas. Each bedroom includes its own en-suite bathroom, while an additional powder room serves the main living space. The bright, open-concept layout is filled with natural light and features large sliding glass doors that overlook the resort-style pool and outdoor entertaining areas. The oversized kitchen is a chef's dream, complete with updated appliances, abundant counter space, a large breakfast bar, and casual dining area. Fully stocked with cookware, dishes, and small appliances, it's ideal for preparing everything from quick breakfasts to gourmet dinners. Multiple living spaces, including a family room with a large flat-screen TV and a cozy fireplace, provide plenty of room for everyone to gather and unwind. Step outside to your own private oasis, featuring a sparkling pool, expansive sun deck, outdoor kitchen with grill, and multiple dining areas that comfortably seat 16 or more guests. Surrounded by mature landscaping, the outdoor living space offers exceptional privacy and the perfect setting for entertaining, relaxing, or enjoying Florida's beautiful weather. Golf enthusiasts will appreciate the home's proximity to The Highlands Golf Course, a scenic par-72 championship course known for its tree-lined fairways, generous greens, and classic Old Florida character. Just moments from your doorstep, the course offers a memorable golfing experience enhanced by GPS-equipped golf carts and modern course technology. There is an abundant amount of Activities and Attractions in Sarasota/Bradenton. These are just a few of the many treasures and cultural events: Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, Museum of the Circus, Childrens fountain at Island Park, Myakka River and Park, Ed Smith Stadium Sport Complex, Sarasota Ballet (Oct-Apr), Van Wezel Performing Arts, Florida Studio Theatre, Sarasota Opera House, The Asolo Theatre, and Players Theatre. 2 Month Minimum Stay required. There is a 13% Tax and Cleaning Fee of $650.00. 50% of Total Rental amount is due upon booking the reservation, and the balance due 90 days prior to the arrival date. No pets please. CANCELLATION: In the event the Tenant cancels the reservation, they are responsible for the entire amount of the rent and tax. If the Landlord is able to re-lease the premises for the entire time frame of the Guest License Agreement, they will refund Tenant’s money, minus 3.5% of the rental amount for processing fees. n lieu of a damage deposit, guests will be charged a fee of $14.00 a night to cover any damages up to $3,000. The $11,00 is for base rent only. There are taxes, an insurance fee, cleaning fees, credit card fee, and pool heating fee.
6005 MIDNIGHT PASS RD #N13, SARASOTA, FL 34242
$2,800362 Days on yellowkey MLS ID: A4660736
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 748 Built: 1967Community: Provincial GardensVilla
Remarks: Welcome to Sunrise Porch Lookout — your peaceful intercoastal retreat in the heart of Siesta Key. This bright and tropical second-floor condo is perfectly situated in the highly sought-after Provincial Gardens community, where Old Florida charm meets serene waterfront beauty. Overlooking the intercoastal waterway and lush park-like lawn, the screened-in wraparound porch is your front-row seat to sunrise skies, drifting sailboats, and a cool morning breeze. This one-bedroom condo offers a king bed, spacious living area, and a small but fully equipped kitchen ideal for light meals or snacks between beach outings. The interior is designed in a cheerful, nautical palette with comfy furniture, modern conveniences, and thoughtful touches throughout. Natural light pours in from windows that frame the stunning water views, creating a welcoming and relaxing space. Guests of Sunrise Porch Lookout enjoy shared private beach and pool access via neighboring Aloha Kai — just across the street. Relax by the heated pool, explore Siesta Key on foot or by bike, and return to your porch to watch the golden hour settle over the water. With on-site parking, in-unit laundry, and beach gear provided, this getaway is as convenient as it is scenic. Enjoy direct access to Crescent Beach, kayak the calm waters of the intercoastal, or indulge in local seafood at nearby favorites like Captain Curt’s, Big Water Fish Market, and the original Daiquiri Deck. You're just minutes from Siesta Key Village, Turtle Beach, and even downtown Sarasota via the nearby Stickney Point Bridge. **Why Guests Love It:** - Wake up to intercoastal water views every morning - Peaceful, non-commercialized community with tropical landscaping - Ideal for couples, snowbirds, and solo travelers looking to relax - No elevators or crowds — just tranquility and sunshine Professionally hosted & part of the SV Collection — a handpicked portfolio of unique vacation homes across Siesta Key. Property Manager has the most updated availability calendar available. **PLEASE NOTE** Rates vary by week/season. Additional fees and taxes apply. During the months of January, February, and March, there is a 1 month minimum rental period and check-in & check-out dates are only allowed on the first and last day of those months.
Listing is courtesy of: CONCESSION REAL ESTATE COMP. (941-388-0501)
Listing Agent: Susan Saltalamacchia (941-408-6622)
1250 N PORTOFINO DR #302, SARASOTA, FL 34242
$3,150361 Days on yellowkey MLS ID: A4660757
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1969Community: Siesta Harbor IiCondo
Remarks: 55+ Harbor View Haven on Siesta Key w/beach access! Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether you're boating, fishing, or enjoying community events, your stay will be unforgettable. The master bedroom boasts a queen bed, TV, ensuite bathroom, and a walk in closet, along with access to the screened porch. The second bedroom also has a queen bed and shares a bathroom with a tub/shower combo. The bright living room includes a TV, while the fully equipped kitchen and dining area offer all the amenities needed for a delightful stay. Enjoy the covered and screened porch area, perfect for sipping your morning coffee or watching the boats in the harbor. As a guest at our Siesta Harbor condo on Siesta Key, you'll have access to a variety of amenities designed to enhance your stay. The Siesta Harbor community offers a fishing pier, perfect for those who enjoy fishing or simply being by the water. For boating enthusiasts, boat slips are available for vessels up to 30 feet, with direct access to the Intercoastal Waterway (monthly fee applies). The clubhouse features a library and pool table, and hosts various community activities. You'll also have access to a heated swimming pool and hot tub for a refreshing swim or a relaxing soak, as well as a shuffleboard area and grills for outdoor fun and dining. Enjoy deeded beach access to the pristine sands and beautiful sunsets of Siesta Key Beach and Crescent Beach. Beach chairs are also onsite in the unit for your use. The building includes an elevator for convenient access and a same-level laundry room for guests' use. Experience the perfect blend of relaxation, community engagement, and coastal living at our Siesta Harbor condo. Welcome to your home away from home in beautiful Siesta Key! This 2-bedroom, 2-bathroom condo is designed for comfort and relaxation. The master bedroom boasts a queen bed, TV, ensuite bathroom, and walk-in closet, along with access to a serene covered porch. The second bedroom also has a queen bed and shares a bathroom with a tub/shower combo. The bright living room includes a TV, while the fully equipped kitchen and dining area offer all the amenities needed for a delightful stay. Enjoy the covered and screened porch area, perfect for sipping your morning coffee or watching the boats in the harbor. Book your stay and experience the tranquility of Siesta Harbor! **PLEASE NOTE** Rates vary by week/season. Additional fees and taxes apply. During the months of January, February, and March, check-in & check-out dates are only allowed on the first and last day of those months.
323 MADISON DR, SARASOTA, FL 34236
$25,50029 Days on yellowkey MLS ID: A4697742
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1377 Built: 1953Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Remarks: Booked September or pool install, October 8th-12th, Dec. 18th 2026-January 1st 2027 Professional Pictures coming soon! Welcome to your perfect St. Armand's getaway! This beautifully updated 3-bedroom, 2-bath home offers comfort, style, and an unbeatable location just around the corner from world-famous St. Armands Circle and Lido Beach. Designed for relaxation and quality time together, the home features a cozy family room, spacious dining area, and a fully equipped kitchen with brand-new appliances. Whether you're preparing a quick breakfast before the beach or gathering for a family dinner, you'll have everything you need for a memorable stay. Each bedroom is thoughtfully furnished to provide a comfortable retreat, while the two full bathrooms offer convenience for families and groups. Step outside to enjoy the private backyard, the perfect spot for morning coffee, afternoon sunshine, or unwinding after a day at the beach. With new furnishings throughout the home, guests will appreciate the fresh coastal feel and inviting atmosphere. Located in the heart of St. Armands, you'll be within walking distance of renowned restaurants, boutique shopping, ice cream shops, and local attractions. Lido Beach is just minutes away, making it easy to spend your days soaking up the Florida sunshine and Gulf Coast beauty. Whether you're planning a family vacation, a couples' escape, or a long-term island stay, this charming home offers the perfect combination of location, comfort, and convenience. Experience the best of Sarasota's island lifestyle from this charming St. Armands retreat! The $25,500 is for base rent only. There are taxes, insurance fee, cleaning fees, credit card fee, and pool heating fee. Please note-the driveway can accomodate 2 cars. Street parking is available for a fee. Street parking is available from 8 am to midnight with no overnight parking. You may park in the parking garage and the Filmore parking lot overnight. (More detailed info in the house manual)
6005 MIDNIGHT PASS RD #S4, SARASOTA, FL 34242
$6,000359 Days on yellowkey MLS ID: A4660901
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1210 Built: 1966Community: Provincial GardensVilla
Remarks: Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With beachside BBQs, shuffleboard, and plenty of amenities, this charming villa offers comfort and convenience for an unforgettable stay. The Space: This delightful 2-bedroom, 2-bath unit is designed with your relaxation in mind. The main bedroom features a king-sized bed for restful nights, while the second bedroom offers two cozy singles—ideal for family or guests. The living room includes a sofa bed and TV, perfect for unwinding after a day of adventure. Prepare meals in the fully equipped kitchen and enjoy dining indoors or on the screened patio with a table and chairs. Start your mornings or enjoy evenings on the outdoor seating area by the entrance. A gated courtyard with a BBQ grill is great for outdoor gatherings, and an onsite washer and dryer add convenience to your stay. Guest Access & Amenities: Guests have access to deeded beach entry via Aloha Kai, just across the street, making beach days easy and carefree. Dive into the largest heated swimming pool on Siesta Key or relax on poolside lounges with ample seating and shade. Boating and fishing enthusiasts will appreciate the private day-use dock with a kayak lift (kayaks not provided). The beautifully landscaped park-like setting offers serene bay views with comfortable seating to soak it all in. Beach chairs and other extras are provided to enhance your beach and pool experience. The Neighborhood: Situated in the peaceful Provincial Gardens area of Siesta Key, this villa offers the perfect blend of tranquility and convenience. Siesta Key Public Beach is nearby, renowned for its white sand, clear waters, and family-friendly amenities like volleyball courts, tennis courts, picnic areas, and a playground. The Village on Siesta Key, a short distance away, is the island’s vibrant hub—packed with shops, restaurants, and regular live music and events. Near the South Bridge, you’ll find convenient shopping, grocery stores, and a range of dining options from casual to upscale. Provincial Gardens itself is a calm, park-like community that provides a relaxing escape while keeping you close to all the key attractions. Whether you want a laid-back beach day or an adventurous outing, everything Siesta Key offers is within easy reach. Professionally hosted & part of the SV Collection — a handpicked portfolio of unique vacation homes across Siesta Key. Property Manager has the most updated availability calendar available. **PLEASE NOTE** Rates vary by week/season. Additional fees and taxes apply. During the months of January, February, and March, there is a 1 month minimum rental period and check-in & check-out dates are only allowed on the first and last day of those months.
1255 DOCKSIDE PL #211, SARASOTA, FL 34242
$3,600359 Days on yellowkey MLS ID: A4660925
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1982Community: Harbour TowneCondo
Remarks: Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is just a short walk from the world-famous Siesta Key Beach. Whether you’re looking to relax or stay active, this inviting property offers everything you need for an unforgettable vacation. The Space: Step inside this peaceful condo featuring a spacious main bedroom with a luxurious king bed, vaulted ceilings, and serene water views. The main bedroom also includes a private ensuite bathroom for added convenience. The second bedroom offers two cozy twin beds, while a loft area with a queen bed provides flexible sleeping or a quiet spot to unwind. Enjoy morning coffee or evening breezes on the covered, screened porch overlooking the water and boat harbor. The open living area flows into a fully equipped kitchen with a bar seating area—ideal for casual meals or entertaining. Guest Access & Amenities: Guests have access to a private attached garage for secure parking, a heated swimming pool, and a tennis court for friendly matches. Boating enthusiasts will appreciate the private boat dock on the property. For outdoor gatherings, the covered pavilion with BBQ grills is perfect for cookouts and socializing. Explore the neighborhood with two complimentary bicycles provided, and relax at the beach with a beach umbrella and seven chairs included. Siesta Key Public Beach is just a short stroll away, offering soft white sand and crystal-clear waters. The Neighborhood: Located in the peaceful Harbour Towne community, this condo puts you close to all Siesta Key has to offer. The vibrant Village on Siesta Key is nearby, featuring unique shops, diverse dining options, and regular live events. Near the South Bridge, you'll find convenient shopping and a variety of restaurants from casual to upscale. Enjoy beach volleyball, tennis courts, playgrounds, picnic areas, and the laid-back island atmosphere all within easy reach. Whether you want to lounge on the beach, savor fresh seafood, or explore local culture, this condo is your perfect base for experiencing Siesta Key’s natural beauty and charm. Professionally hosted & part of the SV Collection — a handpicked portfolio of unique vacation homes across Siesta Key. Property Manager has the most updated availability calendar available. **PLEASE NOTE** Rates vary by month/season. Additional fees and taxes apply. During the months of January, February, and March, check-in & check-out dates are only allowed on the first and last day of those months.
228 VAN BUREN DR, SARASOTA, FL 34236
$18,750716 Days on yellowkey MLS ID: A4619895
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1862 Built: 1984Community: St Armands Div/John Ringling ESpa: YesSingle Family
Remarks: **Welcome to your perfect vacation retreat!** This beautiful 4-bedroom, 3-bath home offers a light-filled, open-concept floor plan designed for comfort, relaxation, and entertaining. **Price for August-October is $18,000** Booked: August 11th-20th, Dec 27th 2026-March 15th 2027, March 27th-April 25th 2027 The thoughtfully designed multi-level layout provides plenty of space and privacy for everyone. The **upper level features the luxurious primary suite with its own spacious en-suite bathroom**, complete with a soaking tub and separate shower for the ultimate spa-like experience. Also on the upper level is an additional **en-suite guest bedroom**, perfect for family members or guests seeking extra privacy. The **middle level offers two additional bedrooms and a full bathroom**, creating comfortable accommodations for larger groups. On the **ground level, you'll find the resort-style outdoor living area, pool access, and laundry room**, along with an additional refrigerator for added convenience. The stunning updated kitchen features granite countertops, stainless steel appliances, and a convenient breakfast bar—perfect for gathering with family and friends. Adjacent to the kitchen, the dining area overlooks the sparkling pool and comfortably seats eight guests. Step outside to your own private resort-style oasis. Enjoy the pool and spa, unwind in the covered lounge area, dine al fresco under the covered seating area, or fire up the grill for a memorable evening outdoors. For even more fun, challenge your family and friends to a game of ping pong or cornhole. If you'd like to explore the area on two wheels, bicycles may be available during your stay—just let us know in advance, and we'll be happy to help arrange them. **With spacious accommodations, resort-style amenities, and a layout designed for both togetherness and privacy, this home has everything you need for an unforgettable getaway.** There is an abundant amount of Activities and Attractions in Sarasota/Bradenton/Siesta. These are just a few of the many treasures and cultural events..Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, Florida?s Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, Museum of the Circus, Children's fountain at Island Park, Myakka River and Park, Ed Smith Stadium Sport Complex, Sarasota Ballet (Oct-Apr), Van Wezel Performing Arts, Florida Studio Theatre, Sarasota Opera House, The Asolo Theatre, and Players Theatre. Leisure time can be spent on shops, galleries, golfing, tennis, ice skating, water sports like; fishing, snorkeling, kayaking, diving, jet skis, water skiing or leisure boating. You can spend the entire day at our famous St. Armand's Circle with its award winning indoor or outdoor dining, upscale shopping, and galleries. People from around the world come to choose from one of our many famous beaches: Siesta Key, Longboat Key, Lido Key, Bradenton Beach, and Anna Maria Beach. The famous white sands of Lido Beach are just steps away, offering sunsets of a lifetime! The $18,750 is for base rent only. There are taxes, an insurance fee, cleaning fees, credit card fee, and pool heating fee.
1025 VILLAGIO CIR #208, SARASOTA, FL 34237
$1,67547 Days on yellowkey MLS ID: A4696723
REDUCED by $50 (2.9%) on 07/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 2002Community: VillagioCondo
Elementary School: Tuttle Elementary
Remarks: Stunning water views from every room will make you fall in love with this home. This beautiful 2 Bedroom / 2 Bathroom unit, located on the second floor, is available now for annual rent. You'll love the high ceilings in the living room area right as you enter. The bright condo features an open floor plan with a comfortable living/dining room area and a kitchen with plenty of storage and a breakfast bar, perfect for entertaining or a quick meal. The primary bedroom has a spacious walk-in closet and features an ensuite bathroom with a shower. The guest bedroom is conveniently located on the other side of the home, providing privacy and plenty of storage room. The second bathroom is located right next door and features a bathtub. The unit has laminated flooring throughout the living room space and carpet in the bedrooms. An extra storage nook / office space plus a laundry closet with your own washer and dryer finish the unit off. Two covered, reserved parking spots will keep your cars protected from the elements. The unit is nestled within the gated Villagio condominium association, minutes away from downtown Sarasota, shopping and beautiful beaches, with easy access to 301, I75 and public transportation. Community amenities include a heated resort-style pool, tennis/pickle ball court, playground and gym. Rent is $1675 (utilities are not included). First month's rent plus security deposit (equal to one months' rent) is required prior to moving in. The Villagio charges $100.- per person for the background check. Unfortunately, pets are not allowed, and it is a non-smoking unit. RoseBay International Realty doesn't manage this unit, we solely help the landlord to secure a new tenant. Please contact us today to schedule a showing in person or a virtual tour.
Listing is courtesy of: CENTURY 21 ROSEBAY (941-366-7673)
Listing Agent: Corinne Gillett (941-321-8330)
125 S BLVD OF PRESIDENTS, SARASOTA, FL 34236
$24,0002472 Days on yellowkey MLS ID: A4449134
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3043 Built: 1956 Tax: $26,568 (2021)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$26,568
Remarks: This property is on the market and as of now will not be renting in 2027. Booked: July 17th-August 9th, Nov. 21st-28th, Dec. 21st-31st 2026 Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps 8, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa, or investigating St. Armand's Circle or Lido Beach. Professionally decorated, quality surrounds you whether it be the wonderful appliances, the new furniture or the luxurious bedding. There is seating at the dining table for 8 and room for more at the breakfast bar. There is also a bedroom and bathroom located over the garage. Walk 150 yards to St. Armand's for dinner or night out, before returning to a lighted heated pool and spa to end the evening. The pool deck is complete with recliners, chairs and a dining table for real outdoor living. Retire to comfy new beds which will ensure a blissful sleep to start the new day. Visit this home once and you will return! There is a gate to the driveway but it is not operational at this time. There are many places to visit around the area some of those include, Mote Marine, Selby Gardens, Marina Jacks, Island Park, and many theatre options as well. You can also find that adventurous side and go water skiing, boating, golfing, or just relax on one of our luxurious beaches. This property is leased on a first come, first serve basis. If we reply the property is available, it is at that moment, but may become unavailable before you can book it. We suggest you book as soon as possible to not loose your favorite vacation rental. The $24,000 is for base rent only. There are taxes, an insurance fee, cleaning fees, credit card fee, and pool heating fee. City of Sarasota Certificate VR22-00089
85 S POLK DR, SARASOTA, FL 34236
$26,2502134 Days on yellowkey MLS ID: A4479064
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3462 Built: 1958 Tax: $29,058 (2021)Community: Lido Beach Div BSpa: YesSingle Family
Taxes:$29,058
Remarks: Booked; July 18th-August 8th, August 23rd-31st, September 25th-November 14th, November 24th-Dec. 6th, Dec. 25th 2026-April 30th 2027. Welcome to this stunning waterfront retreat on beautiful Lido Key, where luxury, comfort, and coastal living come together. Perfectly situated on a wide canal with a private dock and boat lift, this home offers direct access to Sarasota Bay and is ideal for boating, fishing, paddleboarding, or simply enjoying the peaceful water views. Inside, the bright open floor plan features elegant coastal décor, soaring ceilings, and a beautifully appointed chef's kitchen with quartz countertops, custom cabinetry, premium stainless-steel appliances, a gas cooktop, and an oversized island perfect for gathering with family and friends. The spacious living and dining areas flow seamlessly to the outdoor entertaining space. The luxurious primary suite is a private sanctuary featuring a spa-inspired bathroom with a freestanding soaking tub, oversized walk-in shower, and direct access to the pool area. Each bedroom includes a flat-screen TV, while the family room offers a large-screen TV for movie nights and relaxing evenings. Step outside to your own tropical oasis complete with a heated pool and spa, lounge chairs, BBQ grill, and multiple seating areas overlooking the canal. Enjoy your morning coffee by the water, spend the day poolside, and gather around the fire pit as the sun sets. Just minutes from the famous white sands of Lido Beach and the shops and restaurants of St. Armands Circle, this exceptional waterfront home offers the perfect setting for an unforgettable Florida getaway. Boater's if you plan to dock a boat at the house, in order to exit the canal and enter Sarasota Bay, you will have to clear the Ringling Relief located under South Blvd. of Presidents. The $26,250 is for base rent only. There are taxes, an insurance fee, cleaning fees, credit card fee, and pool heating fee. City of Sarasota Certificate VR22-00087
8449 LUNAR SKYE ST, SARASOTA, FL 34241
$2,3002 Days on yellowkey MLS ID: A4701141
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1553 Built: 2022Townhouse
Remarks: AVAILABLE OCTOBER, 2026 as annual unfurnished rental. The Marigold is a 1,553 sq. ft. END UNIT townhome with 3 bedrooms, 2.5 bathrooms and a 1-car garage, set amid the tranquil community of The Townhomes at Skye Ranch. Inside, you are met with a spacious gathering room and an open-concept designer kitchen, highlighted by the outstanding natural light that streams in from the lanai that has private views of the preserve . On the first-floor level, a 1-car garage and a half bath are present for added convenience. Upstairs, you can explore the 2 secondary bedrooms sharing a full bath and a large Main Suite with an oversized walk-in closet and a double-sink vanity. Space is not a concern within the Marigold, with the multiple storage areas including under stair storage, a large walk-in kitchen pantry, separate laundry room upstairs next to the main bedroom, linen closet, and more! The amenities are located one street away and include a sparkling pool and restrooms. Look at the floor-plan at thetownhomesatskyeranch then choose the Marigold floor-plan. available October 1, 2026. One small pet allowed with approval.
Listing is courtesy of: REALTY BY DESIGN LLC (941-779-4509)
Listing Agent: Brian Odonnell (941-779-4509)
55 N WASHINGTON DR, SARASOTA, FL 34236
$21,0003173 Days on yellowkey MLS ID: A4200349
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3071 Built: 1960 Tax: $18,524 (2021)Community: St Armands Div/John Ringling ESingle Family
Taxes:$18,524
Remarks: Booked currently for Nov. 22nd-Nov 29th, Dec 23rd 2026-Jan 1st 2027, March 13th-20th, March 27th-April 3rd, April 10th-17th 2027 St. Armand's Circle, the famous vacation destination in Florida, is home to this beautifully decorated 6 bedroom 4.5 bath vacation home (which includes a 1 bedroom/1 bath attached bedroom and bath off of the garage). A wonderful 2 story pool home with granite kitchen, formal dining area, wood flooring which sleeps (14). The floor plan boasts an eat-in kitchen with breakfast table and breakfast bar. The house is equipped with wi-fi and TV's in most bedrooms. The sliding glass doors lead to the gorgeous backyard featuring an outdoor pool where the sun is waiting to warm your body and spirit! The $21,000 is for base rent only. There are taxes, an insurance fee, cleaning fees, credit card fee, pool heating fee, and pet fee if bringing a dog. City of Sarasota Certificate VR22-00148
5152 NORTHRIDGE RD #204, SARASOTA, FL 34238
$1,59556 Days on yellowkey MLS ID: A4695868
0 Days Off yellowkey (back on 7/29/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1116 Built: 1999Community: Serenade On Palmer RanchCondo
Elementary School: Ashton Elementary
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Nice condo located on second floor in gated community within Palmer Ranch. This is a desirable gated community with two heated pool, hot tub, fitness center, and tennis court. Close to Siesta Key Beach, I-75, restaurants and shopping. Inside unit laundry, extra vanity outside of bathroom for added convenience, screened lanai, large walk-in closet, and open kitchen/living area all make this a very comfortable place to live.
Listing Agent: Maureen Plichta (941-812-5799)
12724 LATERAL ROOT DR, SARASOTA, FL 34238
$2,89516 Days on yellowkey MLS ID: A4699876
REDUCED by $50 (1.7%) on 07/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1839 Built: 2022Community: Promenade Estates Ph IiSingle Family
Elementary School: Lakeview Elementary
High School: Venice Senior High
Remarks: This beautifully maintained 4 bedroom, 2 bathroom single-family home puts space, privacy, and convenience front and center. An open-concept kitchen with stainless steel appliances flows into tile-floored living areas, while the private owner's suite, in-unit washer/dryer, and 2-car garage deliver everyday ease. Outside, a covered patio make this pet-friendly rental perfect for entertaining or simply unwinding. Located in a quiet, family-friendly community near shopping, top-rated schools, parks with easy access to the highway and employment hubs, this move-in ready home is freshly touched up, professionally cleaned, and fully inspected, ready for you today. ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit Available for minimum one-year lease with option to renew. HOA Application Fee: $100; 14-day approval timeframe Tenant Responsible for: Electric & Water Pets: Small pet (dog/cat) negotiable. 1 pet maximum. $25/mo. pet rent and $250 refundable pet security deposit. Security Deposit Option: Ask about applying for a zero-security deposit option through our partnership with The Guarantors. At PMI Southwest Florida, we strive to provide an experience that is cost effective and convenient. That’s why we provide a Resident Benefits Package (RBP) to address common headaches for our residents. Our Standard Program handles insurance, air filter changes, utility set up, credit building, rent rewards and more at a rate of *$39.95/month, added to every property as a required program. You have the option to elect our Premium Program, which includes all of the above plus identity protection & pest control at a rate of *$49.95/month. *If you provide your own insurance policy, the RBP cost will be reduced by $11.95, which is the amount of the insurance premium billed by Second Nature Insurance Services This home also comes with high speed internet up to 1 Gig at an exclusive group rate of $65.00, and includes 24/7 premium support and setup to help get you connected at move-in.
Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)
Listing Agent: Brandon Green (941-806-9963)
1640 STICKNEY POINT RD #40-101, SARASOTA, FL 34231
$2,100228 Days on yellowkey MLS ID: A4674926
REDUCED by $200 (8.7%) on 06/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1101 Built: 1975Community: Castel Del MareSpa: NoCondo
Elementary School: Gulf Gate Elementary
Remarks: Available Now Through December 2026 – $2,100/Month Enjoy the best of Siesta Key living in this beautifully updated, fully furnished ground-floor condo located in the sought-after waterfront community of Castel Del Mare. Thoughtfully appointed for comfort and convenience, the unit features a full-size washer and dryer, a reserved parking space, and stylish furnishings throughout, making it ideal for an extended stay. The location is hard to beat—just a 10-minute walk to world-famous Crescent Beach and within easy walking distance of restaurants, shopping, jet ski rentals, and other island attractions. Bike to Siesta Key Village or take the free trolley to explore the island with ease. Residents enjoy an impressive array of resort-style amenities, including two heated swimming pools, tennis and pickleball courts, a kayak launch, a fishing pavilion, scenic waterfront boardwalks, beautifully landscaped grounds, and professional on-site management. This turnkey rental is available now through December 2026 for $2,100 per month. Please note that the property is not available for the 2027 season (January through March).
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
6020 MIDNIGHT PASS RD, SARASOTA, FL 34242
$2,50014 Days on yellowkey MLS ID: A4700119
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1964Spa: NoApartment
Remarks: DIRECT BEACH ACCESS! Beautifully located 1 bed/1 bath second-floor unit in the sought-after Aloha Kai community on Midnight Pass Rd, This fully furnished unit offers relaxing pool views and is move-in ready in this well-maintained beachside community. Available for 2 adults, no pets. Water and electricity included in rent. On-site parking available. Steps from the sand — perfect for tenants wanting a true island lifestyle. Won't last long — schedule your showing today!
Listing is courtesy of: ROELENS REALTY & PROPERTY MANA (239-887-7674)
Listing Agent: Koen Roelens (239-887-7674)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.