156

Homes for Rent in Siesta Key, FL with 2-Bedrooms

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  • /28

    $10,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft
    • House for Rent

    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

    6042 W Peppertree Way Unit 224B, Sarasota, FL 34242
  • /26

    $7,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Condo for Rent

    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

    Unlisted Address
  • /21

    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    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

    1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
  • /14

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,110 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 64, Sarasota, FL 34242

    Villa 64 at Aloha Kai is located on Siesta Key, a beloved barrier island on Florida’s West Coast. This comfortable and spacious unit features 2 bedrooms, 2 baths, and a set of twin bunk beds—perfect for families or groups. For your convenience, the villa also includes a washer and dryer. Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach, consistently

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 64, Sarasota, FL 34242
  • /12

    $8,340 Per Month

    • 2 Beds
    • 1.5 Baths
    • 836 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit D02, Sarasota, FL 34242

    Newly furnished and redecorated with a beachy vibe! Both bedrooms have new premium mattresses. Master bedroom has a king size mattress with 1.5 bath ensuite Second bedroom is furnished with two twin mattresses. Flat screen TVs in both bedrooms. Living room has two new Lazy Boy sofa sleepers. Individual in villa wi-fi. Just steps to one of the large pools on Siesta Key or choose a day on the beach

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit D02, Sarasota, FL 34242
  • /27

    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,455 Sq Ft
    • Condo for Rent

    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

    1195 Coquille St Unit 309, Sarasota, FL 34242
  • /19

    $8,370 Per Month

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 31, Sarasota, FL 34242

    You’ll love the light, bright coastal décor of the beautifully appointed and inviting Villa 31 at Aloha Kai. This little piece of paradise offers effortless living and a stay so enjoyable, leaving feels impossible. Located 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

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 31, Sarasota, FL 34242
  • /18

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • House for Rent

    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

    6154 Midnight Pass Rd Unit B06, Sarasota, FL 34242
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    $12,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • House for Rent

    301 Avenida Madera Unit B, Sarasota, FL 34242

    Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright

    Robert Bevington SHOWTIME REALTY

    301 Avenida Madera Unit B, Sarasota, FL 34242
  • /10

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    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

    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
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    $8,010 Per Month

    • 2 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • House for Rent

    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

    1205 E Peppertree Dr Unit 232, Sarasota, FL 34242
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    $7,000 Per Month

    • 2 Beds
    • 11 Baths
    • 1,163 Sq Ft
    • Condo for Rent

    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

    1200 E Peppertree Ln Unit 602, Sarasota, FL 34242
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    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • Condo for Rent

    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

    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
  • /48

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • House for Rent

    4830 Higel Ave, Sarasota, FL 34242

    More pictures to come, waiting for the rest of the furniture to arrive. Florida charm at it’s best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the Sarasota School of Architecture. The home is on 1/3 of an acre on the Grand Canal with a dock and kidney-shaped heated pool. The new hardwood flooring and new impact windows make this home bright and

    toyia Youtzy JENNETTE PROPERTIES, INC.

    4830 Higel Ave, Sarasota, FL 34242
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    $7,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft
    • Condo for Rent

    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

    1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
  • /22

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Apartment for Rent

    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

    1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242
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    $6,400 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    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.

    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
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    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    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

    1250 N Portofino Dr Unit 303, Sarasota, FL 34242
  • /42

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Condo for Rent

    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

    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
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    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    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

    1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
  • /10

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,071 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit A06, Sarasota, FL 34242

    Enjoy a perfect vacation in this spacious 2 bedroom, 2 bath large villa. With 2 Queen and 2 Twin beds, this is the perfect villa even for a large family up to 6. From this villa, you are just steps to Crescent Beach - world renowned whitest sand. Enjoy Wi-Fi community internet access, a 32" flat screen TV with HD/DVD in the living room, and a TV with DVD/VHS in the master bedroom. Kids will enjoy

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit A06, Sarasota, FL 34242
  • /12

    $8,340 Per Month

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • Apartment for Rent

    6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242

    Experience breathtaking, unobstructed views of the sparkling Gulf of Mexico and the pristine shores of Crescent Beach from the spacious 3rd-floor lanai of this beautifully appointed two-bedroom, two-bathroom beachfront apartment. Perfectly designed for comfort and relaxation, this well-maintained unit features a fully equipped kitchen with all the essentials needed to prepare everything from

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242
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    $8,370 Per Month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    New photos coming soon! Villa 40 at Aloha Kai offers the perfect beach getaway. With tile floors, tranquil furnishings, and a beautifully updated bath featuring a walk-in shower, this villa invites you to kick off your shoes and stay awhile. The primary bedroom includes an en suite half bath for added privacy and comfort. Enjoy your morning coffee on the enclosed porch or the open patio before

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 40, Sarasota, FL 34242
  • /10

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit D06, Sarasota, FL 34242

    Casa Blanca is within sight of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. Most Villas have a screened Lanai with table and chairs for dining and relaxing. Those without a lanai

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit D06, Sarasota, FL 34242
  • /16

    $8,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft
    • House for Rent

    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

    6030 E Peppertree Way Unit 222A, Sarasota, FL 34242
  • /70

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 896 Sq Ft
    • Condo for Rent

    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

    1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
  • /10

    $9,420 Per Month

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • Condo for Rent

    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

    6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242
  • /18

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    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

    1255 E Peppertree Dr Unit 305, Sarasota, FL 34242
  • /10

    $8,370 Per Month

    • 2 Beds
    • 1.5 Baths
    • 836 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit B04, Sarasota, FL 34242

    This newly furnished and decorated 2 bedroom villa with a brand new king mattress, and sleeper sofa, accommodates up to 6 guests. The master bedroom offers a king bed, private bath and cable TV. The guest bedroom offers 2 twin beds and cable. Villa B4 offers HD TV, DVD, movie choices, surround sound, and wireless internet services. Fully screened lanai offers seating and privacy shades for your

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B04, Sarasota, FL 34242
  • /65

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Condo for Rent

    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

    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
  • /43

    $17,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Condo for Rent

    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

    6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
  • /27

    $6,300 Per Month

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Condo for Rent

    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

    1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
  • /49

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Condo for Rent

    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

    6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242
  • /48

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Condo for Rent

    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

    6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242

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