$9,300 per month
1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,300 per month
1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key*Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,300 per month
1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,300 per month
1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,225 per month
1125 W Peppertree Dr Unit 402, Sarasota, FL 34242
Stylish 2-Bedroom, 2-Bathroom Condo in Peppertree Bay - Siesta Key, FLLooking for the perfect vacation getaway? This stunning 2-bedroom, 2-bathroom condo in the desirable Peppertree Bay community is just what you need! Nestled on the fourth floor, this high-rise retreat offers tranquil pond views and a serene atmosphere.The unit features assigned covered parking under the building for
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$9,200 per month
8710 Midnight Pass Rd Unit 405B, Sarasota, FL 34242
8710 Midnight Pass Rd Unit 405B, Sarasota, FL 34242
$9,000 per month
1343 4th St Unit 101, Sarasota, FL 34236
Live grounded. Create freely. Canvas RADD introduces a single-level, 3-bedroom, 3-bath live/work residence set at street level in Sarasota’s Rosemary Arts and Design District, designed for flexibility, presence, and creative flow in one of the city’s most dynamic neighborhoods. The layout unfolds across one generous level with high ceilings and expansive windows that bring in natural light and
Chase Moore SIGHT REAL ESTATE, LLC
$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
$9,000 per month
1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242
Indulge in coastal luxury with this beautifully decorated Gulfside unit nestled on the 1st floor of a stunning high-rise. With hardwood floors throughout and thoughtfully curated decor, this retreat offers the perfect blend of elegance and comfort. Step into the spacious living area, where natural light floods through large windows, illuminating the stylish furnishings and inviting ambiance. The
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$9,000 per month
1546 Stickney Point Rd Unit 501, Sarasota, FL 34231
Seasonal This sophisticated, coastal-inspired luxury condominium is located in The Boatyard, one of the most sought-after gated communities on the Intracoastal Waterway. Just a short walk from Siesta Key’s gorgeous Crescent Beach, you’ll enjoy effortless access to water sports, shopping, dining, and the vibrant island lifestyle. Your private boat slip is steps away from the carport. The main
Cody Smith RENT SARASOTA
$9,000 per month
8918 Olde Hickory Ave, Sarasota, FL 34238
AVAILABLE JAN 2026 - RENTED JAN., FEB., MARCH., APRIL 2026: IMPRESSIVE SINGLE-FAMILY POOL HOME with paver driveway, two-car garage, and screened entryway, step inside and be delighted! Open floor plan, wood-plank flooring throughout, cathedral ceilings, updated kitchen with stainless steel appliances, lots of cabinets, granite counters, an ample pantry, and open to the living/dining area. The
Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE
$9,000 per month
1 Benjamin Franklin Dr Unit 91, Sarasota, FL 34236
Lido Beach Vacation Rentals. Available for a 4 month minimum for winter season 2027. This 9th floor Lido Beach condo offers outstanding views of the Gulf of Mexico, Lido Beach and St. Armands Circle. Your private beach get-away! A private balcony takes you outdoors along the length of the unit. The primary bedroom offers direct gulf front views to the west and north. The guest bedroom has been
Margaret Young JENNETTE PROPERTIES, INC.
$9,000 per month
327 Avenida Milano, Sarasota, FL 34242
Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully
Chrissie Cummings JENNETTE PROPERTIES INC
$9,000 per month
4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large
Jane Hunter JENNETTE PROPERTIES INC
$9,000 per month
3924 Helene St, Sarasota, FL 34233
This beautiful newly renovated pool home features 3 bedrooms, 2 bathrooms. The home sleeps 6 and is in the neighborhood of Forest Lakes South, Sarasota. Modern updates include new flooring throughout, updated bathrooms & kitchen with new quartz countertops, new exterior facade & new doors. One small dog is allowed. This home provides peaceful pool and pond views from almost every room in the
Jana L. Nizny M&M PROPERTY MANAGEMENT GROUP
$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
$8,970 per month
6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
Find your Happy Place here in this LARGE 2 bedroom/2 bathroom, private entrance villa. There is new granite in the kitchen which is fully equipped. The master bedroom is furnished with a king size bed. The master vanity for the ladies comes with a hairdryer. The master bath features a walk-in shower with new tile and granite, all new from top to bottom. The second bedroom provides two double
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6154 Midnight Pass Rd Unit B06, Sarasota, FL 34242
Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
B11 is a private 2-bedroom, 2-bath villa halfway between the beautiful private Casa Blanca Crescent Beach and the pool. This villa is fully furnished and decorated to meet your needs for a relaxing vacation with all the conveniences of home, including private wireless internet. Enjoy the comforts of this large, fully furnished villa with a spacious living area, fully equipped kitchen, and a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
This is a fun tropically decorated beach villa that will put a smile on your face when you walk in!! This unit can easily occupy up to 6. We have recently remodeled the kitchen and both bathrooms. The master bedroom features a king size bed with a new pillow top mattress. The master bath is new with a roman walk in shower. There is an LCD TV, DVD player and a nice closet. The second bedroom has a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
Welcome to the newly renovated A04 Villa! Private entrance leads to the screened in lanai and open air space which includes the kitchen, dining area and comfortable seating to enjoy the large flat screen tv. The villa sleeps up to 6. 2 queen beds in the primary bedroom and 2 twin beds in the guest bedroom. Both bedrooms are also equipped with flat screen TVs. This large villa features 2
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
Welcome to D18 one of the closest to the beach among the villas.” It consists of two bedrooms and two full bathrooms, each of which contain a walk-in shower. The master bedroom has a king size bed while the second bedroom has a twin and a queen bed. The villa owners regularly update the unit for the comfort of the guests, which includes a TV in the master bedroom and a large screen TV in the main
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6020 Midnight Pass Rd Unit 59, Sarasota, FL 34242
Villa 59 at Aloha Kai invites you to kick back and escape the traffic and long lines—no need to leave the property! Enjoy the pristine beach, the refreshing pool, and your fully equipped kitchen, all designed to make your stay effortless and relaxing. The comfortable furnishings and soothing neutral colors create a welcoming atmosphere where you can truly feel at home. Savor your morning coffee
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6020 Midnight Pass Rd Unit 2, Sarasota, FL 34242
Villa 2 at Aloha Kai is beautifully situated on Siesta Key, a popular barrier island along Florida’s West Coast. This family-friendly, gated resort community is nestled in the heart of Crescent Beach, which is ranked as the number one beach in the continental United States. Known for its dazzling white quartz sand and vibrant emerald-green waters, Siesta Key is among Florida’s top vacation
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
Villa 1 at Aloha Kai is ideally situated on Siesta Key, a popular barrier island along Florida’s West Coast. Nestled within the family-friendly, gated resort community of Aloha Kai, it lies in the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation.
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6020 Midnight Pass Rd Unit 20, Sarasota, FL 34242
Lush tropical landscaping surrounds the screened-in porch of Villa 10 at Aloha Kai, offering endless hours of relaxation in a serene setting. This one-bedroom, one-bath villa also features a private patio for your enjoyment. The kitchen is bright, well-appointed, and equipped with everything you need for cooking and dining. The spacious bedroom provides ample closet space for your comfort. Known
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,970 per month
6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242
Starting at $299/night! Explore a luxurious studio-style condominium at Casa Mar, featuring one bathroom and a queen-sized murphy bed. This elegant retreat boasts a fully equipped kitchen that flows into a spacious dining area, ideal for hosting guests. Benefit from the convenience of a private carport just a few steps away from your residence. Casa Mar offers an impressive range of amenities,
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
$8,900 per month
1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,900 per month
1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,800 per month
6030 E Peppertree Way Unit 222A, Sarasota, FL 34242
This property is a 30 night minimum. 6030 is a small garden unit, located on the Bayside of Midnight Pass Ground Floor unit. 2 bedroom, 2 bath unit . Approx. 1250 Sq. Ft. (1350 including the lanai). Bedding:Master bedroom: KingGuest Bedroom: Queen Electronics:Living room: 32 inch Flat PanelMaster Bedroom: 20 inchGuest Bedroom: 12 inch Bathrooms:Master: ShowerGuest:
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,700 per month
6020 Midnight Pass Rd Unit 35, Sarasota, FL 34242
Toes in the sand and sunshine on your shoulder—welcome home to the spacious one-bedroom Villa 35 at Aloha Kai. This beautifully updated villa features granite countertops in both the kitchen and bath, while the bedroom offers ample space and a large closet. The open-concept layout extends to a front porch enclosed with windows and blinds, providing additional living space and privacy. Located on
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$8,700 per month
5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,
Beth Dilley ASCENDIA REAL ESTATE
$8,580 per month
1102 Benjamin Franklin Dr Unit 514, Sarasota, FL 34236
Lido Beach condo in Lido Surf and Sand, with a large porch overlooking views north up Lido Beach. Step into this split plan two bedroom, two bathroom condo with views that are breathtaking. The condo has porcelain tile floors and stylish furniture.
C. Alison Hunter JENNETTE PROPERTIES INC
$8,550 per month
6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
Welcome to Villa #27, your home away from home on beautiful Crescent Beach, Siesta Key. As one of Aloha Kai’s closest villas to the Gulf of Mexico, you are just steps away from the top-rated beach in the United States. The villa’s décor is comfy and casual, featuring two sofas, a dining table that seats six, and an open kitchen—perfect for relaxing evenings in. Kick back and enjoy a late-night
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
$8,500 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
$8,500 per month
5247 Carmilfra Dr, Sarasota, FL 34231
5247 Carmilfra Dr, Sarasota, FL 34231
$8,500 per month
301 Quay Commons Unit 509, Sarasota, FL 34236
Modern coastal luxury condominium in Sarasota’s vibrant downtown bayfront at Bayso Sarasota. This rare offering is ideally located on the highly desirable 5th-floor amenity level and features a unique floor plan with the largest private south-facing terrace on the level, offering exceptional outdoor living for relaxing and entertaining. The residence offers 2 bedrooms plus den, 3 full baths, and
Connie Marois Pozo CORCORAN DWELLINGS REALTY
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