$9,500 Per Month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
$6,080 Per Month
5760 Midnight Pass Rd Unit SI ID1385989P, Siesta Key, FL 34242
The advertised rate of $6,080/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 6, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
(941) 394-8699
$8,500 Per Month
1195 Coquille St Unit 309, Sarasota, FL 34242
1195 Coquille St Unit 309, Sarasota, FL 34242
$6,397 Per Month
6265 Midnight Pass Rd Unit SI ID1383701P, Siesta Key, FL 34242
The advertised rate of $6,398/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 13, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
(941) 231-5174
$22,000 Per Month
3939 Higel Ave, Sarasota, FL 34242
3939 Higel Ave, Sarasota, FL 34242
$13,000 Per Month
5624 Cape Leyte Dr, Sarasota, FL 34242
5624 Cape Leyte Dr, Sarasota, FL 34242
$6,300 Per Month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
$15,000 Per Month
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
$9,500 Per Month
1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,410 Per Month
5855 Midnight Pass Rd Unit SI ID1385908P, Siesta Key, FL 34242
The advertised rate of $6,411/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$7,400 Per Month
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle
Andy Moore GULF COAST REALTY & MANAGEMENT
$3,900
Total Monthly Price
1055 W Peppertree Dr Unit 5th, Sarasota, FL 34242
Beach front…water and Sun set views…modern…I king size bed and full bathSecond bedroom 2 full size beds and a full bathHuge porch with beach front views…Available 5/1 till 11/30 with some flexibility…
$7,500 Per Month
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is
Robert Bevington SHOWTIME REALTY
$3,500
Total Monthly Price
1300 N Portofino Dr Unit 205, Siesta Key, FL 34242
Welcome to your newly renovated dream coastal escape in beautiful Siesta Harbor on Siesta Key, Sarasota, Florida, USA! This turnkey furnished; spacious one-bedroom, two-bath condo featuring brand new furniture is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short 5-minute stroll, you'll enjoy
$5,970 Per Month
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$1,695 Per Month
5215 Calle de Costa Rica Unit C, Siesta Key, FL 34242
$8,500 Per Month
5216 Calle de Costa Rica, Sarasota, FL 34242
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
Beth Dilley ASCENDIA REAL ESTATE
Call for Price
797 Beach Rd Unit 305, Sarasota, FL 34242
Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and
$9,500 Per Month
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and
Andy Moore GULF COAST REALTY & MANAGEMENT
$3,300 Per Month
4822 Ocean Blvd, Sarasota, FL 34242
Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass
$7,050 Per Month
1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$2,200 Per Month
111 Pass Key Rd, Siesta Key, FL 34242
Available off season till 10/31/26 for $2200 per month!!! Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ
$9,500 Per Month
1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,000 Per Month
5400 Ocean Blvd, Sarasota, FL 34242
SEASONAL OR ANNUAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it's best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280
$3,200 Per Month
4660 Ocean Blvd Unit P1, Sarasota, FL 34242
Price Reduced! Turnkey Furnished Waterfront Condo on Siesta Key Enjoy stunning views of Big Pass and the Gulf from this beautifully updated condo in Sea Village. This light-filled unit features new floors, crown molding, hurricane-impact sliders, and an open living/dining layout. The kitchen offers wood cabinetry, granite countertops, a breakfast bar, and quality appliances. The primary suite
Nelson Reyes SHOWTIME REALTY
$9,975 Per Month
3919 Roberts Point Rd, Sarasota, FL 34232
Located on Siesta Key with just a 3 minute walk to Shell Beach, this 2-story home is available NOW & FURNISHED for an ANNUAL LEASE.The kitchen flows seamlessly with an OPEN LAYOUT into the expansive living and dining areas filled with NATURAL LIGHT from the large sliding glass doors opening to the SCREENED-IN LANAI.The POOL & HOT TUB/SPA, also screened-in, are framed by lush
$5,370 Per Month
6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,470 Per Month
6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,500 Per Month
1256 Riegels Landing Dr, Sarasota, FL 34242
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
Christopher Davenport STARLINK REALTY INC
$15,000 Per Month
5516 Avenida Del Mare, Sarasota, FL 34242
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
Beth Dilley ASCENDIA REAL ESTATE
$5,000 Per Month
1255 E Peppertree Dr Unit 306, Sarasota, FL 34242
2 BR - 2 BA - 6 Person Max - High-rise - Greenbelt View This property is a 30 night minimum.1255 - 306 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Hardwood floors on the lanai. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master Bedroom: King - Guest Bedroom:
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$9,000 Per Month
6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$12,296 Per Month
6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$5,200 Per Month
1255 E Peppertree Dr Unit 602, Sarasota, FL 34242
Enjoy Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to the #1 beach in the US with white powder sand and warm gulf waters. Enjoy beautiful views of the gulf from our full-length lanai and both bedrooms.The condominium offers multiple heated swimming pools, beach side and bay side grills, fishing pier, and a recently renovated exercise
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,600 Per Month
1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your
Andy Moore GULF COAST REALTY & MANAGEMENT
$5,000 Per Month
1257 S Portofino Dr Unit 36, Sarasota, FL 34242
Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open
Margaret Young JENNETTE PROPERTIES, INC.
$6,000 Per Month
5157 Sandy Beach Ave, Sarasota, FL 34242
Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee at LeLu Coffee Lounge. 4 bedrooms and 2.5 baths brings you back inside with a
Joseph Meszaros M&M PROPERTY MANAGEMENT GROUP
$7,000 Per Month
1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$3,500 Per Month
1215 S Portofino Dr Unit 308, Sarasota, FL 34242
BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
$8,370 Per Month
6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
Villa 45 at Aloha Kai is a light-filled coastal retreat featuring an updated kitchen that perfectly complements its bright, beachy furnishings. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king bed and two twin beds, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
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Siesta Key, located on a barrier island off the coast of Sarasota, Florida, is renowned for its pristine Siesta Beach, which boasts white quartz sand and was ranked the No. 2 beach in the United States by TripAdvisor in 2023. The island spans 8 miles, with most homes and activities concentrated on the north end, particularly around the downtown area and the quaint village district. This area features a variety of unique shops, restaurants, and nightclubs, enhancing the island's vibrant local flavor. Residents enjoy great walkability and a convenient trolley service that traverses the island. Housing options on Siesta Key include modern styles, Spanish Mediterraneans, ranch-style homes, cozy cottages, coastal-style homes, and several condominium complexes with amenities like pools and tennis courts. Dining highlights include the Toasted Mango Café, Miguel’s, and Captain Curt’s Crab & Oyster Bar, located roughly 3 miles south along the Midnight Pass corridor. The island also offers attractions such as Crescent Beach and Turtle Beach, with facilities for tennis, volleyball, and fishing. Education is served by the highly rated Out-of-Door Academy on the island and top-rated Sarasota County Schools, including Southside Elementary, Brookside Middle, and Riverview High. Siesta Key is accessible via the Siesta Key North Bridge and the Stickney Point Bascule Bridge, with the Sarasota Bradenton International Airport just 10 miles away.
There are currently 268 homes available for rent in Siesta Key, FL. The median rent is $4,500 per month, with condos at $4,500.
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