268

Siesta Key, FL Homes for Rent

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  • 6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242
    /15

    $6,900 Per Month

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

    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242

    Welcome to Villa B07! This unit has been completely renovated with all new flooring, walls, windows, doors, kitchen cabinets, granite countertop, state-of-the-art stainless-steel appliances, a new full bath with walk-in shower and new vanity, new half bath with new vanity, and a new hot/cold shower on the outside of the villa. The two bedrooms sleep 4 comfortably but there is a queen-sized

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    /30

    $8,970 Per Month

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

    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242

    Villa 1 at Aloha Kai is ideally situated on Siesta Key, a popular barrier island along Florida’s West Coast. Nestled within the family-friendly, gated resort community of Aloha Kai, it lies in the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
  • 1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
    /31

    $9,300 Per Month

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

    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

    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    /14

    $8,370 Per Month

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

    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Villa 54 at Aloha Kai is your ideal beach retreat, spacious, sun-filled, and designed for total relaxation. This corner villa features an open floor plan with abundant natural light, custom cabinetry, and thoughtful upgrades throughout. The updated kitchen includes stainless steel appliances and is fully equipped to make meal prep easy, while the in-unit washer and dryer add everyday convenience

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • 1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
    /24

    $11,105 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Apartment for Rent

    1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242

    This property is a 30 night minimum. This 2 bedroom, 2 full bath unit is located in a Gulfside Highrise, only steps from Crescent Beach. An open concept living space flows nicely from the formal dining to spectacular views of Peppertree Pond on the lanai. The living area has plenty of comfortable seating for the entire family, a 55" Smart TV, and glass door lanai access. The kitchen has been

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242
    /17

    $10,200 Per Month

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

    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242

    Welcome to Casa Blanca A-15, your beautiful beach retreat just steps from the powdery white sands of Siesta Key’s private Crescent Beach. This spacious, totally remodeled (August 2025) 2- bedroom, 2-bath villa blends coastal charm with modern comfort, offering everything you need for a relaxing getaway.Step inside and feel the open, airy flow of this sunlit villa. The master suite features an

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242
  • 1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
    /24

    $7,000 Per Month

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

    1125 W Peppertree Dr Unit 501, Sarasota, FL 34242

    2 BR -- 2 BA -- 4 Person Max -- High Rise -- Beach and Pond View1125-501 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx. 175 yards away from Crescent beach.Open kitchen floor plan with recessed lighting. Granite counters, Stainless steel fridge. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai).Condo

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
  • 1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    /26

    $9,300 Per Month

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

    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

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242
    /21

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242

    Lush tropical landscaping surrounds the screened-in porch of Villa 10 at Aloha Kai, offering endless hours of relaxation in a serene setting. This one-bedroom, one-bath villa also features a private patio for your enjoyment. The kitchen is bright, well-appointed, and equipped with everything you need for cooking and dining. The spacious bedroom provides ample closet space for your comfort. Known

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242
  • 1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
    /27

    $7,000 Per Month

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

    1125 W Peppertree Dr Unit 701, Sarasota, FL 34242

    2 BR -- 2 BA -- 4 Person Max -- High Rise -- Beach ViewThis property is a 30 night minimum.This 2 bedroom, 2 bath is in a Gulf-side High-rise unit, located approximately 175 yards from Crescent Beach.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and beautiful views of the beach through the lanai sliding glass doors. The master bathroom has a tub/shower combination

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
  • 1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
    1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
    1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
    /19

    $5,500 Per Month

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

    1255 E Peppertree Dr Unit 501, Sarasota, FL 34242

    Welcome to this beautifully remodeled Bayside Mid-rise unit. This spacious 2-bedroom, 2-bathroom condo is situated on the 5th floor, As you step inside, you'll be greeted by a tastefully decorated living area with modern furnishings and a serene coastal color palette. The open-concept design seamlessly connects the living, dining, and kitchen areas, creating a perfect space for relaxation and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
  • 1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    /31

    $7,500 Per Month

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

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242

    Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The condo is in a Gulf-side High-rise building on the 5th floor. Assigned covered parking located in the parking garage under the building.A luxurious dining area greets you as you enter, that flows through to the living room and out to the lanai. The lanai works as an extended living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
    /22

    $8,340 Per Month

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

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242

    Enjoy your beach vacation in this beautiful large 2 bedroom, 2 bathroom private villa. Located halfway between the private beach and the pool/clubhouse. This unit can sleep up to 6 comfortably. Flat screen HD TV's in the living room and in each bedroom and ceiling fans throughout. Updated with tile throughout, and fully appointed kitchen with new stainless steel appliances. Roomy master bedroom

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242
    /11

    $7,470 Per Month

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

    6154 Midnight Pass Rd Unit B03, 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 B03, Sarasota, FL 34242
  • 6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
    6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
    6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
    /29

    $10,700 Per Month

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

    6018 W Peppertree Way Unit 231B, Sarasota, FL 34242

    Paradise awaits you at Siesta Key! Experience the beauty of the #1 Beach in the USA with this gorgeous 2 bedroom 2 bath stunning beach view condo overlooking the pool. This beautiful condo is just steps from the pool and Direct Beach Access. Amenities for the complex include: 2 fitness centers, 2 heated pools, a fishing pier, 2 clubhouses, pickle-ball and tennis courts. You will enjoy hopping on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
  • 327 Avenida Milano, Sarasota, FL 34242
    327 Avenida Milano, Sarasota, FL 34242
    327 Avenida Milano, Sarasota, FL 34242
    /84

    $9,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • House for Rent

    327 Avenida Milano, Sarasota, FL 34242

    Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

    Chrissie Cummings JENNETTE PROPERTIES INC

    327 Avenida Milano, Sarasota, FL 34242
  • 1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    /27

    $12,000 Per Month

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

    1305 Siesta Bayside Dr Unit 1305B, 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

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
  • 345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
    /98

    $18,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • House for Rent

    345 Avenida Leona, Sarasota, FL 34242

    Listing reflects peak season rate. 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 bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • 6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
    /25

    $7,650 Per Month

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

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
  • 1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
    /26

    $6,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Apartment for Rent

    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

    This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai). Condo

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
  • 6039 E Peppertree Way Unit 222, Sarasota, FL 34242
    6039 E Peppertree Way Unit 222, Sarasota, FL 34242
    6039 E Peppertree Way Unit 222, Sarasota, FL 34242
    /21

    $7,800 Per Month

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

    6039 E Peppertree Way Unit 222, Sarasota, FL 34242

    This property is a 30 night minimum.This 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass.The master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head.The guest bedroom has a king bed, a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6039 E Peppertree Way Unit 222, Sarasota, FL 34242
  • 1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
    /33

    $6,000 Per Month

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

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

    Welcome to your slice of paradise in Gulf & Bay Club Bayside, a highly sought-after community located on beautiful Siesta Key, Florida. Professionally managed by Gulf Coast Vacation rentals, this first-floor 2-bedroom, 2-bathroom lakefront condo offers the perfect blend of coastal charm and resort-style living. From the moment you step inside, you’ll be greeted by a beachy, relaxed vibe that

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
  • 5151 Oakmont Place, Sarasota, FL 34242
    5151 Oakmont Place, Sarasota, FL 34242
    5151 Oakmont Place, Sarasota, FL 34242
    /44

    $2,950 Per Month

    • 3 Beds
    • 2 Baths
    • 1,953 Sq Ft
    • House for Rent

    5151 Oakmont Place, Sarasota, FL 34242

    Welcome to your dream home at 5151 Oakmont Place, nestled in the heart of the stunning Siesta Key, Sarasota, FL. This charming 3-bedroom, 2-bathroom residence offers 1,953 square feet of modern living space, designed for both comfort and style. Step inside to discover a thoughtfully laid-out floor plan that seamlessly blends contemporary design with functionality. The kitchen is a chef's delight,

    Beth Harris COMPASS FLORIDA LLC

    5151 Oakmont Place, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
    /25

    $27,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242

    When only the best will do, Villa 26 at Aloha Kai is the perfect choice. Beautifully updated with meticulous attention to detail, this beachfront villa offers an ideal retreat where you can watch shorebirds, dolphins, and breathtaking sunsets from your private porch. The kitchen is a chef’s dream, while the bathrooms provide a spa-like experience for ultimate relaxation. Located on Siesta Key, a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
    /22

    $8,370 Per Month

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

    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242

    Early risers and night owls can live in harmony at Villa 50 at Aloha Kai, where the thoughtful layout features bedrooms upstairs and a convenient bathroom downstairs. This beautifully renovated villa boasts new flooring, an updated kitchen with stainless steel appliances, granite countertops, and modern bathrooms. Whether you're enjoying a meal in the spacious dining room or dining al fresco on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
  • 446 Canal Rd Unit 5, Sarasota, FL 34242
    446 Canal Rd Unit 5, Sarasota, FL 34242
    446 Canal Rd Unit 5, Sarasota, FL 34242
    /64

    $2,450 Per Month

    • 2 Beds
    • 1 Bath
    • 680 Sq Ft
    • Condo for Rent

    446 Canal Rd Unit 5, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season weekly rate. Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything you need

    Beth Dilley ASCENDIA REAL ESTATE

    446 Canal Rd Unit 5, Sarasota, FL 34242
  • 5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    /57

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

    Listing reflects off-season rate. Available August - December 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 to unwind. Step

    Beth Dilley ASCENDIA REAL ESTATE

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
  • 1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
    1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
    1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
    /25

    $6,500 Per Month

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

    1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242

    Heaven on Siesta Key, in perfect condition, up to date, and simply beautiful. This spacious, first floor one bedroom with a bay/harbor water view from your lanai is immaculate, beautifully decorated and offers every comfort for your favorite vacation stay. The modern kitchen shines with new cabinets, lighting, paint, and kitchen work desk. Elegant bathroom with new walk in shower featuring

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
  • 1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
    1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
    1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
    /29

    $5,700 Per Month

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

    1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242

    Charming 2 bedroom/ 2 bath Condo just a short walk to the beach. Come enjoy our key-west style condo with a very rare 2 car garage. Two swimming pools, tennis court, pickleball, workout room and fishing dock round out the amenities on our lushly landscaped property. Nestled between palm trees, this ground floor condo does not have a unit above it. Impeccably clean and comfortable with a fully

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
  • 4900 Ocean Blvd Unit 501, Sarasota, FL 34242
    4900 Ocean Blvd Unit 501, Sarasota, FL 34242
    4900 Ocean Blvd Unit 501, Sarasota, FL 34242
    /89

    $4,700 Per Month

    • 3 Beds
    • 3 Baths
    • 1,867 Sq Ft
    • Condo for Rent

    4900 Ocean Blvd Unit 501, Sarasota, FL 34242

    Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the tropical

    Beth Dilley ASCENDIA REAL ESTATE

    4900 Ocean Blvd Unit 501, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242
    /13

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242

    New photos coming soon! Villa 51 at Aloha Kai is a beautifully updated retreat that offers the perfect setting for your beach getaway. Begin your day with coffee in the light and airy kitchen, then step out to enjoy it on your private front porch or back patio. The spacious living room features designer plantation shutters on the sliding doors, providing both elegance and privacy. The bedroom

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
    /19

    $7,470 Per Month

    • 1 Bed
    • 10 Baths
    • 728 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

    Casa Blanca offers this charming 1 bedroom/1 bath villa in Siesta Key on the Gulf of Mexico. Spend your vacation in Villa A01, conveniently located to the pool and just a three-minute walk to Siesta Keys Crescent Beach, voted #1 beach in the US! This beautiful beach has soft; white quartz sands, a shade area and guests are provided with private access.The villa comes fully furnished and is a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
  • 6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
    6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
    6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
    /27

    $2,800 Per Month

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

    6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

    Welcome to Sunrise Porch Lookout — your peaceful intercoastal retreat in the heart of Siesta Key. This bright and tropical second-floor condo is perfectly situated in the highly sought-after Provincial Gardens community, where Old Florida charm meets serene waterfront beauty. Overlooking the intercoastal waterway and lush park-like lawn, the screened-in wraparound porch is your front-row seat to

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242
    /11

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242

    Villa 38 at Aloha Kai offers a spacious living area that opens onto an enclosed porch—perfect for enjoying your morning coffee. Its unique design features beamed ceilings and eclectic furnishings, creating a charming beach bungalow atmosphere. The fully equipped kitchen has everything you need to prepare meals to enjoy on the patio, and a convenient walk-in shower adds to your comfort. Located on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242
  • 1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    /31

    $9,300 Per Month

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

    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

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
  • 6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
    /28

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

    Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
    /10

    $8,970 Per Month

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

    6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242

    This is a fun tropically decorated beach villa that will put a smile on your face when you walk in!! This unit can easily occupy up to 6. We have recently remodeled the kitchen and both bathrooms. The master bedroom features a king size bed with a new pillow top mattress. The master bath is new with a roman walk in shower. There is an LCD TV, DVD player and a nice closet. The second bedroom has a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /39

    $2,995 Per Month

    • 2 Beds
    • 1.5 Baths
    • 981 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    Welcome to this Siesta Key Florida fully furnished town house for rent, located on the barrier island of Siesta Key Florida #1 beach in USA, made famous for its pure quartz sugar sand. A truly tropical beach front community Sandy Cove in Siesta Key with private fishing pier, small private beach and beautiful ocean view, and only one block from Siesta Key Village. A rarely available 2 bedroom two

    Matthew fehniger JJF REALTY INC

    Unlisted Address
  • 1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
    /27

    $5,700 Per Month

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

    1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242

    Steps from beautiful Crescent Beach, this fully renovated 2 bedroom 2 full bathroom unit is located in Gulf-side High-rise on the 8th floor. Step into the extended living lanai area to experience wrap around views of the gulf. Enjoy a window bench, choice of comfy loveseats, or dine with a view of the blue waters and white sand.An updated kitchen with stainless steel appliances peeks through

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
    /15

    $8,970 Per Month

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

    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242

    Welcome to the newly renovated A04 Villa! Private entrance leads to the screened in lanai and open air space which includes the kitchen, dining area and comfortable seating to enjoy the large flat screen tv. The villa sleeps up to 6. 2 queen beds in the primary bedroom and 2 twin beds in the guest bedroom. Both bedrooms are also equipped with flat screen TVs. This large villa features 2

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242

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