$3,000
Total Monthly Price
- 1 Bed
- 1 Bath
- 797 Sq Ft
- Condo for Rent
5683 Midnight Pass Rd Unit 105, Siesta Key, FL 34242
$3,000
Total Monthly Price
5683 Midnight Pass Rd Unit 105, Siesta Key, FL 34242
$4,900 Per Month
5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242
Property Id: 2528213Experience the best of coastal living in this beautifully appointed beachside residence located within the highly desirable Siesta Key community of Gulf Haven. Perfectly positioned just steps from the sugar-white sands and turquoise waters of the Gulf, this charming 1-bedroom, 1-bathroom condo offers the relaxed luxury and island lifestyle that makes Siesta Key one of
(941) 404-7666
$5,525 Per Month
726 Birdsong Ln, Sarasota, FL 34242
AVAILABLE after June 1, 2026! Enjoy your own slice of paradise on World Famous Siesta Key! This beautifully renovated turnkey 3-bedroom, 2-bath heated pool home is just a short distance from the #1-rated beaches and the charming shops and restaurants of Siesta Key Village. Whether you're here for million-dollar sunsets, endless watersports, the famous Sunday Drum Circle, or simply peaceful days
Scott Nold TNG REAL ESTATE
$7,850 Per Month
Unlisted Address
FULLY FURNISHED AND INTERIOR DESIGNED 2 BEDROOM / 2 BATH UNIT now available in Harbor Towers on Siesta Key. This beautifully designed condo offers a total of 1,700 sq ft of indoor/outdoor living, including 1,152 sq ft of air-conditioned space and a spacious 540 sq ft private patio finished with travertine and turf. The unit features 9 ft ceilings, floor-to-ceiling windows, stylish furnishings,
Andres Ospina Rivera LPT REALTY, LLC
$9,975 Per Month
3919 Roberts Point Rd, Sarasota, FL 34242
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 TROPICAL
Benjamin Schwab KEYRENTER SARASOTA PROPERTY MANAGEMENT
$11,000 Per Month
681 Avenida de Mayo, Sarasota, FL 34242
Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply
Colette Jay HORIZON REALTY INTERNATIONAL
$12,000 Per Month
1355 S Portofino Dr Unit 103, Sarasota, FL 34242
Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This
Teresa Ribaudo JENNETTE PROPERTIES INC
$8,500 Per Month
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242
Located in the heart of Siesta Key, live the island lifestyle year-round in this stunning turnkey furnished townhome, tucked away in a quiet enclave of only six residences, offering the perfect blend of privacy, comfort, and convenience. Available now for annual lease.This immaculate and spacious townhome features 3 bedrooms, 2.5 baths, and tasteful coastal furnishings throughout. Upon
Chrissie Cummings JENNETTE PROPERTIES INC
$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
$2,950 Per Month
5151 Oakmont Place, Sarasota, FL 34242
Welcome to your dream home at 5151 Oakmont Place, nestled in the heart of the stunning Siesta Key, Sarasota, FL. This charming 3-bedroom, 2-bathroom residence offers 1,953 square feet of modern living space, designed for both comfort and style. Step inside to discover a thoughtfully laid-out floor plan that seamlessly blends contemporary design with functionality. The kitchen is a chef's delight,
Beth Harris COMPASS FLORIDA LLC
$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
$22,000 Per Month
3939 Higel Ave, Sarasota, FL 34242
3939 Higel Ave, Sarasota, FL 34242$6,000 Per Month
5400 Ocean Blvd Unit 5-3, 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
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
$3,400 Per Month
4660 Ocean Blvd Unit G1, Sarasota, FL 34242
Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added
Beth Dilley ASCENDIA REAL ESTATE
$8,000 Per Month
431 Island Cir, Sarasota, FL 34242
This is a short term rental. Listing reflects off season rate. New to the rental market! Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Island Retreat offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and Siesta Key Village make it an exceptional choice for creating unforgettable memories. Featuring 5
Beth Dilley ASCENDIA REAL ESTATE
$10,000 Per Month
5628 Cape Leyte Dr, Sarasota, FL 34242
Your cozy getaway awaits in Siesta Key at this terrific house. With three bedrooms featuring a king, queen, and full bed, guests find plenty of space to relax. The large heated pool gives you an amazing space for relaxing after a day at the beach which is just steps away. You also have a large gazebo adjacent to the pool to get out of the sun and showcase you BBQ skills. Whether you’re unwinding
Troy Jenkins REALTY EXECUTIVES GALLERY
$2,995 Per Month
Unlisted Address
Welcome to this Siesta Key Florida fully furnished town house for rent, located on the barrier island of Siesta Key Florida #1 beach in USA, made famous for its pure quartz sugar sand. A truly tropical beach front community Sandy Cove in Siesta Key with private fishing pier, small private beach and beautiful ocean view, and only one block from Siesta Key Village. A rarely available 2 bedroom two
Matthew fehniger JJF REALTY INC
$12,000 Per Month
307 Avenida de Paradisio, Sarasota, FL 34242
Welcome to your dream escape on Siesta Key—a completely reimagined coastal retreat designed to make every moment unforgettable.Tucked away on a quiet stretch of Avenida de Parasido, this stunning 3-bedroom, 2-bath home has been fully remodeled from top to bottom with brand-new, designer furnishings. Everything is fresh, pristine, and waiting, be among the very first to experience it.Step
Beth Dilley ASCENDIA REAL ESTATE
$3,200 Per Month
5141 Saint Albans Ave, Sarasota, FL 34242
Available on an annual basis, come escape to relaxed island living in this elevated 2-bedroom, 2-bathroom Siesta Key cottage. Tucked away on a quiet, tree-lined street and set on a large lot with tropical landscaping and low maintenance, it offers both privacy and ease. Just 2 miles from Siesta Key Beach, it’s an easy bike ride or drive to the world-famous white sands, making beach days
Anthony Dalesandro BRIGHT REALTY
$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
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
$12,600 Per Month
301 Avenida Madera Unit A, Sarasota, FL 34242
If you’re searching for the perfect location for your next vacation, your search ends here!This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid
Robert Bevington SHOWTIME REALTY
$12,600 Per Month
301 Avenida Madera Unit B, Sarasota, FL 34242
Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright
Robert Bevington SHOWTIME REALTY
$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
$9,500 Per Month
5400 Ocean Blvd Unit 10-02, Sarasota, FL 34242
Welcome to The Terrace 10-2 on Siesta Key, a fully renovated 10th-floor beachfront condo offering some of the most breathtaking panoramic views on Florida’s Gulf Coast. Designed by the renowned architect Frank Folsom Smith, The Terrace stands as one of Siesta Key’s most architecturally significant landmarks, combining mid-century sophistication with timeless coastal beauty. The Space This
Sean Altice ALTEZ VACATIONS, LLC
$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…
$3,950 Per Month
131 Whispering Sands Cir Unit V33, Sarasota, FL 34242
Live the Siesta Key lifestyle in this beautifully updated 2-bedroom, 2-bath residence offering approximately 1,600 sq ft of usable living space, tucked inside one of the island’s most desirable 55+ Gulf-front communities, just a short stroll to Siesta Key Village. The additional square footage comes from a fully finished garage complete with A/C and a built-in Murphy bed, creating the perfect
Curtis Ware KW COASTAL LIVING III
$6,250 Per Month
4237 Higel Ave, Sarasota, FL 34242
Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking Cocoanut Bayou. Completely private by its original growth of lush tropical landscaping, this property is captivating for all your senses. This 1,500 sqft home was built in 1946 and will wow you from the
Joleisy Machado-Gonzales RELAX PROPERTY GROUP, LLC
$3,300 Per Month
4822 Ocean Blvd Unit 5F, 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
Cody Smith RENT SARASOTA
$15,000 Per Month
5624 Cape Leyte Dr, Sarasota, FL 34242
5624 Cape Leyte Dr, Sarasota, FL 34242$6,397
Total Monthly Price
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
$8,062
Total Monthly Price
5855 Midnight Pass Rd Unit SI ID1385908P, Siesta Key, FL 34242
The advertised rate of $8,063/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 26, 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
$5,891
Total Monthly Price
5760 Midnight Pass Rd Unit SI ID1385989P, Siesta Key, FL 34242
The advertised rate of $5,892/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 30, 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
$6,376
Total Monthly Price
1037 W Peppertree Dr Unit SI ID1386040P, Sarasota, FL 34242
The advertised rate of $6,377/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 26, 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
$6,972 Per Month
6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
New photos coming soon! Villa 36 at Aloha Kai is perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 Per Month
6020 Midnight Pass Rd Unit 61, Sarasota, FL 34242
Villa 61 at Aloha Kai warmly welcomes you with its cheerful coastal décor, designed to help you forget your worries and simply be happy. Its casual, comfortable style will make you feel right at home, while offering the luxury of both beach and pool access—you’ll just have to decide which you prefer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$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
$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
$8,900 Per Month
1055 W Peppertree Dr Unit 302AA, Sarasota, FL 34242
Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a Gulfside Highrise building on the 3rd floor. The kitchen has been renovated with stainless steel appliances and is 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 master bedroom
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$15,000 Per Month
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242Showing Results 1 - 40, Page 1 of 7
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.