248

Siesta Key, FL Homes for Rent with Community Pool

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  • /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
  • /43

    $9,500 Per Month

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • Condo for Rent

    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

    5400 Ocean Blvd Unit 10-02, 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
  • /24

    $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
  • /22

    $7,470 Per Month

    • 1 Bed
    • 1 Bath
    • 612 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 5, Sarasota, FL 34242

    If you’re seeking a peaceful beach hideaway, Villa 5 at Aloha Kai is the perfect escape. Featuring tropical decor, this inviting villa encourages you to kick off your shoes, slip into your bathing suit, and head to the pool or beach. Enjoy the tranquility of the front porch while listening to early morning birdsong or the gentle afternoon breezes. Located on Siesta Key, a popular barrier island

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 5, Sarasota, FL 34242
  • /53

    $5,000 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

    Beachfront Bliss at Casa Mar – Siesta KeyDreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun.Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-white sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim

    Robert Bevington SHOWTIME REALTY

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
  • /47

    $15,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,450 Sq Ft
    • House for Rent

    4879 Commonwealth Dr, Sarasota, FL 34242

    FULLY FURNISHED rental available in Siesta Key, close to the beach and walking distance to Siesta Key Village. RENTAL PRICE depends on total LENGTH OF STAY. Rent a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Boasting

    Daniel Petrilla PREFERRED SHORE LLC

    4879 Commonwealth Dr, Sarasota, FL 34242
  • /19

    $5,070 Per Month

    • 1 Bath
    • 420 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 29, Sarasota, FL 34242

    Starting at $169/night. Discover the perfect beach getaway at our charming studio on beautiful Siesta Key, just steps from the world-famous white sands of Siesta Beach. Ideal for couples or solo travelers, this cozy and well-appointed retreat offers everything you need for a relaxing escape. Nestled in the heart of Siesta Key, you’ll be within easy walking distance of the beach, local shops, and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 29, 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
  • /29

    $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
  • /16

    $10,770 Per Month

    • 4 Beds
    • 4 Baths
    • 1,552 Sq Ft
    • House for Rent

    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

    6020 Midnight Pass Rd Unit 52B, Sarasota, FL 34242
  • /29

    $9,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,310 Sq Ft
    • Townhouse for Rent

    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

    1207 E Peppertree Dr Unit 231, Sarasota, FL 34242
  • /26

    $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
  • /40

    $11,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    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

    1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
  • /46

    $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
  • /30

    $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
  • /15

    $8,010 Per Month

    • 1 Bed
    • 1 Bath
    • 975 Sq Ft
    • House for Rent

    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

    6061 E Peppertree Way Unit 116, Sarasota, FL 34242
  • /27

    $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
  • /79

    $7,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,439 Sq Ft
    • House for Rent

    4852 Featherbed Ln, Sarasota, FL 34242

    SIESTA KEY, Sarasota, Single Family Pool Home....Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

    Jane Hunter JENNETTE PROPERTIES INC

    4852 Featherbed Ln, Sarasota, FL 34242
  • /65

    $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! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light and the relaxed elegance that defines Florida living. Located in a meticulously maintained waterfront community, this spacious unit features an open and inviting layout ideal for seasonal

    Angela Bailey MONARCH PROPERTY GROUP LLC

    1250 N Portofino Dr Unit 303, Sarasota, FL 34242
  • /98

    $8,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,012 Sq Ft
    • Townhouse for Rent

    357 Tierra Mar Ln Unit 5, Sarasota, FL 34242

    Located in the heart of Siesta Key, live the island lifestyle year-round in this stunning turnkey furnished townhome, tucked away in a quiet enclave of only six residences, offering the perfect blend of privacy, comfort, and convenience. Available now for annual lease.This immaculate and spacious townhome features 3 bedrooms, 2.5 baths, and tasteful coastal furnishings throughout. Upon

    Chrissie Cummings JENNETTE PROPERTIES INC

    357 Tierra Mar Ln Unit 5, 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
  • /24

    $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
  • /24

    $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
  • /18

    $7,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    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

    1350 Siesta Bayside Dr Unit 1350B, 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
  • /29

    $8,370 Per Month

    • 1 Bed
    • 1 Bath
    • 802 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 56, Sarasota, FL 34242

    Light, bright, and beachy—Villa 56 at Aloha Kai welcomes you with its retro charm and casual coastal elegance. The inviting interior is enhanced by an updated bath that offers a spa-like retreat, perfect for unwinding after a sun-soaked day at the beach or an afternoon exploring the shops and restaurants in town. In the evening, enjoy a peaceful sunset stroll along the shoreline, then return to

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 56, 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
  • /22

    $7,200 Per Month

    • 1 Bed
    • 1 Bath
    • 959 Sq Ft
    • Condo for Rent

    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

    1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
  • /53

    $5,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft
    • House for Rent

    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

    1224 S View Dr, Sarasota, FL 34242
  • /29

    $7,470 Per Month

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 11, Sarasota, FL 34242

    Feel the sun on your shoulders and sand between your toes when you choose the updated Villa 11 at Aloha Kai. With a spacious front porch and a back patio, this villa offers plenty of opportunities to make the most of your beach getaway. Just steps from the pool and private beach, it’s an ideal retreat for sun lovers. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 11, Sarasota, FL 34242
  • /36

    $14,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,452 Sq Ft
    • House for Rent

    211 Island Cir, Sarasota, FL 34242

    AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

    Brenda Cozy COLDWELL BANKER REALTY

    211 Island Cir, 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

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