$6,300 per month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
$9,500 per month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
$3,600 per month
5223 Shadow Lawn Dr, Sarasota, FL 34242
5223 Shadow Lawn Dr, Sarasota, FL 34242
$8,500 per month
1195 Coquille St Unit 309, Sarasota, FL 34242
1195 Coquille St Unit 309, Sarasota, FL 34242
$4,800 per month
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
4660 Ocean Blvd Unit Q2, 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
$6,508 per month
5855 Midnight Pass Rd Unit ID1385908P, Siesta Key, FL 34242
Feel at home in this 4-bedroom, 3-bathroom condo in Siesta Key, boasting an enclosed lanai and access to community amenities. This 2nd-floor unit is accessible via elevator.This coastal condo features an enclosed lanai with bay views, 3 Smart TVs, a flat-screen TV with cable, a dining table, board games, and a walk-in shower. The kitchen is equipped with an electric stove, Keurig and drip
$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
$3,950 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
$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
$6,397 per month
6265 Midnight Pass Rd Unit ID1383701P, Siesta Key, FL 34242
Feel at home in this 2-bedroom, 2-bath vacation rental in Siesta Key, boasting bay views and beach access.This 1,500 sq ft getaway features a sunroom, free Wi-Fi, 3 Smart TVs, 2 dining tables, ceiling fans, a fully equipped kitchen with a drip coffee maker and cooking basics, and in-unit laundry with a washer and dryer. Towels and linens are provided.Driveway carport parking is available
$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
$17,659 per month
1038 Contento St Unit ID1366625P, Siesta Key, FL 34242
Feel at home in this waterfront, 3-bedroom, 2-bath pool home in the heart of Siesta Key, offering a rare combination of canal-front serenity and walk-to-beach convenience.This waterfront retreat sleeps up to 8 guests and combines the relaxed luxury of island living with unbeatable access to boating, beaches, dining, and Siesta Key Village. The fully equipped kitchen includes a dishwasher,
$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
$6,058 per month
1037 W Peppertree Dr Unit ID1386040P, Sarasota, FL 34242
Feel at home in this modern 2-bedroom condo in Peppertree Bay, offering 1,600 square feet of living space. This single-story condo is located on the 3rd floor and offers step-free entry via the elevator.This condo features smart TVs, a sunroom, a desk workspace, a dining table, a breakfast bar, an en-suite bathroom, and a walk-in closet. Beach towels and snorkeling gear are provided for your
$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
$5,964 per month
5760 Midnight Pass Rd Unit ID1385989P, Siesta Key, FL 34242
Feel at home in this 2-bedroom, 2-bathroom condo in Sarasota, offering 1,435 square feet of living space for a memorable seaside getaway.This beachfront condo features a flat-screen cable TV, DVD player, dining table, en-suite bathroom, and a private screened patio. The kitchen is equipped with a stove/oven, drip coffee maker, Keurig single-serve coffee maker, toaster oven, toaster, blender,
$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
$6,000 per month
140 Ogden St, Sarasota, FL 34242
Property Id: 1174405Completely updated 3 bedroom / 2 bathroom home offers an open floor plan and walk-in closets. 1 car garage and beautiful new pool coming soon! Convenient public access to shell beach on the north end of siesta key and to Gulf beaches close by, kayak access at the end of Ogden Street. Just a short drive to quaint Siesta Key Village. MORE PICS WILL BE UPLOADED THIS
$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
$8,300 per month
1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
This condo is a 30-night minimum.Condo 1200-402 at Peppertree Bay on Siesta KeyThis 2 bedroom, 2 bathrooms recently remodeled, is only steps away from Crescent Beach and is located on the 4th floor.This condo comfortably sleeps 6 guests.The master King bedroom is equipped with a 43'' Smart TV for your entertainment and a ceiling fan. The master bathroom has a walk-in
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.
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