$5,000 Per Month
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
- Condo for Rent
6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
Variable rent based on season
Terry Dorrity INTEGRITY INVESTMENTS REALTY
$5,000 Per Month
6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
Variable rent based on season
Terry Dorrity INTEGRITY INVESTMENTS REALTY
$8,200 Per Month
1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are
Andy Moore GULF COAST REALTY & MANAGEMENT
$10,230 Per Month
6154 Midnight Pass Rd Unit 202, Sarasota, FL 34242
Completely remodeled in 2019. Endless Gulf views from every room. TWO queen sized beds in Master, two twins in second bedroom means plenty of space for your family, and everything is new and sparkling clean! Additional Person fees may apply. Enjoy a dip in one of the largest pools on Siesta Key! This second floor apartment has direct gulf views for stunning sunsets of the only beach to be voted
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,700 Per Month
1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
This two bedroom, two bath ground floor unit is steps from the pool and short distance to the beach. Enjoy all of the amenities that Gulf and Bay Club Bayside has to offer, two swimming pools, 2 pickle-ball courts, tennis, workout room, fishing dock and walking path. Washer and Dryer and one car garage sets us apart from other Siesta Key condos and makes it feel more like a home away from home.
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,000 Per Month
1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,900 Per Month
1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,900 Per Month
1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share
Andy Moore GULF COAST REALTY & MANAGEMENT
$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
$8,400 Per Month
1200 E Peppertree Ln Unit 206, Sarasota, FL 34242
his property is a 30-night minimum.This 2-bedroom, 2 bath has benefits of both sides being located on the bay side with beach access and on the second floor.The master bedroom has a king bed with a 50 inch flat screen TV, a ceiling fan, and access to the lanai. The master bathroom is a walk-in shower with a glass door and a grab bar.The guest bedroom has a king size bed with a 32 inch
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$3,600 Per Month
1255 Dockside Place Unit 211, Sarasota, FL 34242
Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is just a short walk from the world-famous Siesta Key Beach. Whether you’re looking to relax or stay active, this inviting property offers everything you need for an unforgettable vacation. The Space:Step inside this peaceful condo featuring a spacious main bedroom with a
Susan Saltalamacchia CONCESSION REAL ESTATE COMP.
$8,100 Per Month
1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.Step into a sunlit living space adorned with coastal-inspired décor,
Andy Moore GULF COAST REALTY & MANAGEMENT
$5,000 Per Month
1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This 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 Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$10,230 Per Month
6154 Midnight Pass Rd Unit 301, Sarasota, FL 34242
This beautiful condo, is right ON the beach! Siesta Key Beach, designated #1 beach in America, Unit #301 offers a superior, sweeping view of the entire 6 mile long, white sand (quartz) beach. Sliding glass doors open to the lanai and to the living room to allow for sea breezes and sounds of the surf. Each bedroom has the same dramatic view and you are just steps from the beach. Private Wireless
Heather Sutter DESTINATION FLORIDA RENTALS & 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
$9,300 Per Month
1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
This spacious, private and light-colored 2-bedroom/2-bathroom end unit has a lanai that overlooks a lake with frequent bird sightings. Walk right out to an inland waterway and fishing dock. A large, heated pool is just across from the unit. Beach accessories as well as fishing gear and bicycles are available in the private garage.THIS CONDO REQUIRES A TWO WEEK MINIMUM
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,500 Per Month
1195 Coquille St Unit 309, Sarasota, FL 34242
Beautiful 2 Bedroom 2 Bathroom Townhome available! Come see this gorgeous home ready for you to call home! Large living spaces including full kitchen, living room and dining room, 3 seasons room and loft area. Loft area ideal for office space or second floor den. Two large bedrooms including plenty of closet and storage space. Nice patio with grill to enjoy evenings and entertaining. Large full
Anna Fattore COMPASS FLORIDA LLC
$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
$7,000 Per Month
1200 E Peppertree Ln Unit 602, Sarasota, FL 34242
This property is a 30 night minimum.1200-602 is a Penthouse unit in a Bay-side Mid-rise, located approximately 150 yards away from the Bay with a view of the waterway and downtown Sarasota in the distance. Approx. 1200 Sq. Ft. (1462 including the lanai)Lanai has a twin daybed with a trundle, eating area, and desk setup for remote work. Assigned covered parking located in parking garage
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$11,000 Per Month
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach
Andy Moore GULF COAST REALTY & MANAGEMENT
$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
$7,700 Per Month
1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
A spacious two bedroom/two bath ground floor home with attached garage. Relax on the private south-facing lanai overlooking a lake featuring a fountain and frequent visits by numerous water birds. After a long day enjoy HDTV and high-speed internet ready to stream your favorite programs. Wireless internet is also available throughout Bayside and at the pools. The living area is tiled, and the
Andy Moore GULF COAST REALTY & MANAGEMENT
$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.
$3,500 Per Month
1250 N Portofino Dr Unit 303, Sarasota, FL 34242
Available for season 2026/2027! Enjoy true waterfront living on the sought-after barrier island of Siesta Key with direct deeded private beach access to the world-famous white sand beaches. Boat slips are also available for renters, making this the perfect seasonal getaway for beach and boating enthusiasts alike. This updated waterfront condo offers serene canal and Intercostal Waterway views,
Angela Bailey MONARCH PROPERTY GROUP 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
$4,500 Per Month
1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when
Andy Moore GULF COAST REALTY & MANAGEMENT
$7,700 Per Month
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops
Andy Moore GULF COAST REALTY & MANAGEMENT
$7,500 Per Month
1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
This is a short term rental. Listing reflects peak season rate. Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the moon on the water. The spacious living area is bathed in natural light,
Beth Dilley ASCENDIA REAL ESTATE
$9,420 Per Month
6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242
Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach, from the 1st floor of this beautifully appointed two- bedroom, two-bathroom apartment with fully-equipped kitchen. Relax in the living room that overlooks the gulf. Enjoy your morning coffee sitting out on the screened in lanai just steps from the sand.This unit features Private wireless internet, Double
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$6,500 Per Month
1255 E Peppertree Dr Unit 305, Sarasota, FL 34242
his property is a 30 night minimum.1255 - 305 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Open kitchen floor plan. Dual sink vanity in Master bathroom. Living room has a sleeper sofa available. Condo is located on third floor. Equipped with Xfinity cable service and free Wi-Fi. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft.
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,200 Per Month
1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
Relax in the spacious living area or enjoy a glass of wine on the lanai.This 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 Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key!**Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$5,900 Per Month
5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
Available for the 2027 Season or Two Week Rental. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis with a gorgeous view of the heated pool and ICW. Rental is turnkey furnished, decorated for immediate enjoyment with all of the amenities you will need for a relaxing vacation. The stunningly renovated
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
$5,000 Per Month
5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2027-April 2027. Off season rates start at $5,000. 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
Beth Dilley ASCENDIA REAL ESTATE
$7,500 Per Month
6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
No roads to cross to get to the beach! Just listed- This clean, updated, cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your
Robert Bevington SHOWTIME REALTY
$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
$6,300 Per Month
1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,
Andy Moore GULF COAST REALTY & MANAGEMENT
$5,500 Per Month
3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
• UNFURNISHED • ANNUAL RENTAL ~ Rarely available in the exclusive Hamilton Club, this spacious 3-bedroom, 3.5-bath townhome offers over 4,000 square feet of space in one of Siesta Key's most desirable deep-water boating communities. A standout feature of this home is the expansive lower-level garage area, providing exceptional flexibility. In addition to the oversized two-car garage, there is a
Tony Andrews ANDREWS & ASSOCIATES REALTY
$12,000 Per Month
6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242
Siesta Key's beautiful coastline offers you the chance to enjoy your dream vacation in this fantastic 2-bedroom ocean-view condominium. Situated directly on the beach and across the street from the South Village, you’ll be mere steps away from both the beautiful water and a vast array of destinations. The South Village includes a full-service grocery store and numerous restaurants, ice cream
Robert Bevington SHOWTIME REALTY
$10,000 Per Month
6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242
Your Gulf-View Getaway at Siesta Breakers awaits!Wake up to the sparkling blue waters of the Gulf of Mexico in this welcoming 2-bedroom condo at Siesta Breakers on Siesta Key. Just a short stroll brings you to the world-famous Siesta Key Beach, where you can sink your toes into powdery soft whit e sand and swim in crystal-clear waters.If lounging by the pool is more your style,
Robert Bevington SHOWTIME REALTY
$7,000 Per Month
1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
Waterfront Elegance at Marina Del Sol – Your Seasonal Retreat. Indulge in the ultimate Sarasota lifestyle at this stunning 3-bedroom, 2,467 sq. ft. residence in the exclusive Marina Del Sol. Thoughtfully designed and beautifully updated, this spacious condo offers the perfect balance of elegance and comfort, with three oversized porches capturing serene water views and warm coastal breezes. Step
Olga Smith IMPERIAL PROPERTY GROUP LLC
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