$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
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
$5,370 Per Month
6006 Midnight Pass Rd Unit 64, Sarasota, FL 34242
Starting at $179/night! Step into your perfect getaway at this charming ground-floor 1-bedroom unit nestled within the Casa Mar complex, just steps from the beach off Midnight Pass Road. Relax on the screened lanai overlooking a tranquil courtyard, where not one but two inviting pools beckon you to unwind. A leisurely stroll along the sidewalk leads you straight to the sandy shores. Enjoy the
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$7,500 Per Month
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
$8,340 Per Month
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
$8,370 Per Month
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
$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
$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
$12,600 Per Month
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
$7,470 Per Month
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
$5,070 Per Month
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
$8,070 Per Month
6154 Midnight Pass Rd Unit 103, 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 tastefully decorated one bedroom, one bath apartment with tile throughout. Enjoy morning coffee and stunning sunsets on the lanai every day! Newly updated fully equipped kitchen. The property offers one of the largest pools on Siesta Key. Come in, unpack and relax! Siesta Key Beach has
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
$8,010 Per Month
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
$10,770 Per Month
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
$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
$5,800 Per Month
4830 Higel Ave, Sarasota, FL 34242
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 inviting with volume ceiling space. The living room and kitchen offer
toyia Youtzy JENNETTE PROPERTIES, INC.
$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
$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
$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
$7,500 Per Month
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
$8,340 Per Month
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
$8,370 Per Month
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
$7,500 Per Month
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
$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
$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
$8,370 Per Month
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
$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
$5,500 Per Month
5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
SIX+ MONTH RENTAL SPECIAL - OCTOBER 2026 THROUGH MARCH 2027, or Available for the 2027 Season. This beautifully updated 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded vacation retreat with a gorgeous view of the heated pool and ICW. Ten-minute walk or free trolley ride to the famous Siesta Key Beach. Turnkey furnished with all of the amenities you
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
$7,470 Per Month
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
$14,000 Per Month
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
$8,370 Per Month
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
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