$8,500 per month
1195 Coquille St Unit 309, Sarasota, FL 34242
1195 Coquille St Unit 309, 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
$13,000 per month
5624 Cape Leyte Dr, Sarasota, FL 34242
5624 Cape Leyte Dr, 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
$3,500 per month
4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242
Property Id: 2175264This Siesta Key condominium in Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask
$2,295 per month
4822 Ocean Blvd Unit 5E, Sarasota, FL 34242
Beautifully updated waterfront turnkey furnished 1-bedroom condo with breathtaking views of the Gulf of Mexico and Downtown Sarasota, all just a short stroll from the shops, restaurants, and nightlife of Siesta Key Village. RENT NOW WITH ZERO DEPOSIT MOVE IN! Available on a 6 or 12-month lease, this condo is turn-key - just bring your clothes and toothbrush!Rent includes Water, Cable TV and
Andrew Clark SECURE DOOR PROPERTY 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…
$4,750 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
$6,550 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
$7,000 per month
710 Treasure Boat Way, Sarasota, FL 34242
6 to 12 months lease options. $7500 on a 6 month lease and $7000 for a 12 month lease. Ready to move in unfurnished meticulously maintained house for lease. 24 month lease at $6500 a month is a possibility for Lease-To-Own option. Live and experience the magic of the resort feel in the very desired Siesta Beach. Master Suite accessing the pool area 2 other bedrooms sharing one full bath in a
Parvathi Ganduri REAGAN REALTY LLC
$4,750 per month
5354 Shadow Lawn Dr, Sarasota, FL 34242
Available on an Annual Lease. This is a nicely furnished 3 bedroom 2 bath Grand Canal pool home with a deep-water dock on Siesta Key! The home has a foyer entry with etched glass front doors. The open concept floor plan includes living, dining and family rooms which feature pocketing sliding glass doors leading to the large, screened-in lanai, paver deck and sparkling free-form pool overlooking
Todd Roughton SARASOTA MANAGEMENT & LEASING
$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
$5,000 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
Alison Kanter DANIELLE GLADDING & CO. REALTY
$6,000 per month
5310 Hidden Harbor Rd, Sarasota, FL 34242
Siesta Key Annual rental. Located just a half mile from Siesta Key Beach, this four-bedroom, two-bath home is tucked away in the quiet Hidden Harbor area. Set in a beautiful tropical environment with canopy-lined streets, the property features 2,300 square feet of living space and a 1200-square-foot lanai.The interior offers an open floor plan with vaulted ceilings, skylights, and updated
Margaret Young JENNETTE PROPERTIES, INC.
$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
$7,500 per month
1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The condo is in a Gulf-side High-rise building on the 5th floor. Assigned covered parking located in the parking garage under the building.A luxurious dining area greets you as you enter, that flows through to the living room and out to the lanai. The lanai works as an extended living
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,500 per month
1055 W Peppertree Dr Unit 606AA, Sarasota, FL 34242
his condo is in a Gulf-side High-rise on the 6th floor, approximately 75 yards from Crescent Beach.A beautiful remodeled kitchen awaits you with stainless steel appliances, granite counter tops and recessed lighting. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker.The formal dining area has seating for 6 and
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,010 per month
1205 E Peppertree Dr Unit 232, Sarasota, FL 34242
This 2 bedroom, 2 bath is a bay-side townhouse with interior stairs and is approximately 100 yards from the Intracoastal waterway.The master bedroom is upstairs and offers a king bed, a workspace, and beautiful windows to the green gardens outside. The en suite master bathroom has two sinks and a shower/tub combination.The guest bedroom is upstairs and offers 2 twin beds, and the en suite
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$9,500 per month
1207 E Peppertree Dr Unit 231, Sarasota, FL 34242
This 3 bedroom, 3 bath is a townhouse on the bay side of Midnight Pass and is approximately 100 yards from the Intracoastal waterway.The master bedroom has a king bed, a large TV, a ceiling fan, and an en suite bathroom. The master bathroom has a quartz counter, recessed lighting, and a tub/shower combination.The first guest bedroom has a queen bed, a ceiling fan, and a 3/4 guest
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$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
$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
$8,500 per month
1055 W Peppertree Dr Unit 405AA, Sarasota, FL 34242
Nestled just a stone's throw from the pristine sands of Siesta Key beach, this midrise villa offers a luxurious retreat for those seeking a blend of comfort and convenience. With a 30-night minimum stay, guests can fully immerse themselves in the tranquil beach lifestyle. The villa boasts two bedrooms and two bathrooms, accommodating up to four guests, making it an ideal choice for families or
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,000 per month
1224 S View Dr, Sarasota, FL 34242
Stunning Renovated Home for Long-Term Rent in Siesta Cove. Discover your dream coastal lifestyle in this beautifully renovated single-family home located in the exclusive neighborhood of Siesta Cove, just steps away from the acclaimed Siesta Key Beach—voted the number one beach in the United States! This elegant residence boasts 3 spacious bedrooms and 2 luxurious bathrooms, offering a high
Beth Dilley ASCENDIA REAL ESTATE
$3,500 per month
11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242
SIESTA KEY...11 SANDY COVE RD. #8F. This 2 bedroom, 1.5 bathrooms is located in the sought after Sandy Cove Community, just steps away from Siesta Village with its own private beach. Plenty of restaurants and shopping. Enjoy breathtaking Gulf sunsets from this fully turnkey furnished townhouse ready for you to enjoy. Don't miss out on living the Florida life style at its best. Call now for a
Teresa Ribaudo JENNETTE PROPERTIES INC
$17,000 per month
6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
Beachfront Bliss at Casa Mar – Siesta Key Discover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach. Why You’ll Love This Condo: Prime Beachfront Location – Step right onto the powdery whit e sands of Crescent Beach Classic Coastal Charm – Thoughtfully
Robert Bevington SHOWTIME REALTY
$8,000 per month
6044 W Peppertree Way Unit 233B, Sarasota, FL 34242
This property is a 30 night minimum. Welcome to your perfect vacation retreat! This beautifully appointed 3-bedroom, 2-bathroom condo offers the ideal blend of comfort, style, and convenience. Situated in a prime location, this property provides the perfect base for your getaway, whether you’re seeking relaxation, adventure, or a little of both. Step inside to find a spacious open-concept living
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,050 per month
6053 E Peppertree Way Unit 118, Sarasota, FL 34242
This property is a 30 night minimum. This unit has been completely renovated and offers spectacular views of the Intracoastal waterway and pier! The sliders to the lanai open to the screened-in area for fresh air and seamless indoor/outdoor living.The unit offers easy access to the walking paths that leads to the fishing pier and to the bay-side pool and clubhouse.This condo has 2
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$10,700 per month
6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
Paradise awaits you at Siesta Key! Experience the beauty of the #1 Beach in the USA with this gorgeous 2 bedroom 2 bath stunning beach view condo overlooking the pool. This beautiful condo is just steps from the pool and Direct Beach Access. Amenities for the complex include: 2 fitness centers, 2 heated pools, a fishing pier, 2 clubhouses, pickle-ball and tennis courts. You will enjoy hopping on
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,800 per month
6039 E Peppertree Way Unit 222, Sarasota, FL 34242
This property is a 30 night minimum.This 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass.The master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head.The guest bedroom has a king bed, a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,000 per month
6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
This property is a 30 night minimum. 6052 WPW is a Large Garden condo, located approximately 50 yards away from Crescent BeachOpen porch lanai with a 6 person table. Recessed lighting in both bathrooms. Master bathroom has a seat. Recessed lighting in the kitchen. This unit has access to a private garageApprox. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,090 per month
6047 E Peppertree Way Unit 224, Sarasota, FL 34242
6047 is a Bayside Large Garden unit, located approximately 20 yards away from the Intercoastal Waterway. This property is a 30 night minimum. 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding:Master Bedroom: KingGuest Bedroom: 2 Twins Electronics:Livingroom: 60 inch Flat PanelMaster Bedroom: 32 inch Flat PanelGuest Bedroom: 28 inch Flat Panel
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$10,200 per month
6042 W Peppertree Way Unit 224B, Sarasota, FL 34242
his is a 3 bedroom, 2 bathroom, ground floor condo. Sleeps 6How about this location!! Gulf-side close to the Beach, Pool, Clubhouse and Fitness room.Lanai faces due west and you still have your privacy. Split Level unit with your own private one car garage, soaring living room ceiling, open kitchen silestone countertops throughout, new a/c, lanai has its own a/c split system; full size
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$10,770 per month
6020 Midnight Pass Rd Unit 52B, Sarasota, FL 34242
Villa 52N at Aloha Kai offers the perfect escape for your next beach vacation, featuring three comfortable bedrooms and the convenience of an in-unit washer and dryer. Located on Siesta Key—a popular barrier island along Florida’s breathtaking West Coast—this villa is part of Aloha Kai, a family-friendly, gated resort community nestled in the heart of Crescent Beach, consistently ranked the
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,010 per month
6061 E Peppertree Way Unit 116, Sarasota, FL 34242
This property is a 30 night minimum.This 2 bedroom, 1 bath is a second floor garden unit on the bay side of Midnight Pass, and is approximately 15 yards from the Intracoastal waterway.The master bedroom has a queen bed and a 40 inch TV. The master bathroom has a tub/shower combination with a sliding glass door.The guest bedroom has 2 twin beds, a ceiling fan, and window with natural
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
$7,000 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
Showing Results 1 - 40, Page 1 of 7
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.
Copyright © 2026 CoStar Group
