$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
$7,000 per month
1360 Siesta Bayside Dr, Sarasota, FL 34242
This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world- renowned white sandy beach on the
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
$9,350 per month
Unlisted Address
Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,900 per month
1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$15,000 per month
5516 Avenida Del Mare, Sarasota, FL 34242
This is a short term rental. Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. 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
Beth Dilley ASCENDIA 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
$18,000 per month
345 Avenida Leona, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a
Beth Dilley ASCENDIA REAL ESTATE
$12,000 per month
20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$4,500 per month
1257 S Portofino Dr Unit 38, Sarasota, FL 34242
Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the
Kay Esposito SIGNATURE REALTY ASSOCIATES
$5,000 per month
5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot
Beth Dilley ASCENDIA REAL ESTATE
$5,000 per month
6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
Variable rent based on season
Terry Dorrity INTEGRITY INVESTMENTS REALTY
$6,500 per month
1250 N Portofino Dr Unit 102, Sarasota, FL 34242
Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor
Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC
$6,000 per month
5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
** AVAILABLE APRIL 2026! ** BOOKED JANUARY THROUGH MARCH 2026 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the
Kayla Lamb NEXTHOME EXCELLENCE
$7,500 per month
460 Beach Rd Unit A1, Sarasota, FL 34242
Available May 2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the
Brenda Cozy COLDWELL BANKER REALTY
$6,500 per month
1250 N Portofino Dr Unit 301, Sarasota, FL 34242
Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a
Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC
$9,500 per month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
$5,000 per month
1257 S Portofino Dr Unit 36, Sarasota, FL 34242
Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 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 new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach
Margaret Young JENNETTE PROPERTIES, INC.
$6,400 per month
1250 N Portofino Dr Unit 107, Sarasota, FL 34242
This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a full wall length closet for guests. The walk-in closet is reserved for the Owners. The guest bedroom has 2 single beds that can be combined to
Margaret Young JENNETTE PROPERTIES, INC.
$12,000 per month
5519 Azure Way, Sarasota, FL 34242
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all
Catherine Foley JENNETTE PROPERTIES, INC.
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