304

Homes for Rent in ZIP Code 34242

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  • 1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
    /16

    $9,500 Per Month

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

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242

    Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
  • 5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
    /39

    $11,637

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,744 Sq Ft
    • Condo for Rent

    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242

    The advertised rate of $11,637/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
  • 1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
    /35

    $7,400 Per Month

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

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

    Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
  • 6727 Midnight Pass Rd Unit SI ID1578381P, Sarasota, FL 34242
    6727 Midnight Pass Rd Unit SI ID1578381P, Sarasota, FL 34242
    6727 Midnight Pass Rd Unit SI ID1578381P, Sarasota, FL 34242
    /31

    $5,358

    Total Monthly Price

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

    6727 Midnight Pass Rd Unit SI ID1578381P, Sarasota, FL 34242

    The advertised rate of $5,358/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6727 Midnight Pass Rd Unit SI ID1578381P, Sarasota, FL 34242
  • 5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
    /36

    $7,500 Per Month

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

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

    Robert Bevington SHOWTIME REALTY

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • 4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
    /33

    $5,192

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • Condo for Rent

    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242

    The advertised rate of $5,192/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
  • 6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
    /18

    $5,970 Per Month

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

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242

    This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
  • 3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
    3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
    3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
    /40

    $11,340

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Condo for Rent

    3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242

    The advertised rate of $11,340/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
  • 5216 Calle de Costa Rica, Sarasota, FL 34242
    5216 Calle de Costa Rica, Sarasota, FL 34242
    5216 Calle de Costa Rica, Sarasota, FL 34242
    /80

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • House for Rent

    5216 Calle de Costa Rica, Sarasota, FL 34242

    Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key

    Beth Dilley ASCENDIA REAL ESTATE

    5216 Calle de Costa Rica, Sarasota, FL 34242
  • 6703 Midnight Pass Rd Unit SI FL2-ID1591488P, Sarasota, FL 34242
    6703 Midnight Pass Rd Unit SI FL2-ID1591488P, Sarasota, FL 34242
    6703 Midnight Pass Rd Unit SI FL2-ID1591488P, Sarasota, FL 34242
    /23

    $3,699

    Total Monthly Price

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

    6703 Midnight Pass Rd Unit SI FL2-ID1591488P, Sarasota, FL 34242

    The advertised rate of $3,699/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6703 Midnight Pass Rd Unit SI FL2-ID1591488P, Sarasota, FL 34242
  • 5253 Avenida Del Mare, Sarasota, FL 34242
    5253 Avenida Del Mare, Sarasota, FL 34242
    5253 Avenida Del Mare, Sarasota, FL 34242
    /49

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,438 Sq Ft
    • House for Rent

    5253 Avenida Del Mare, Sarasota, FL 34242

    Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key Beach and Siesta Key Village.

    Beth Dilley ASCENDIA REAL ESTATE

    5253 Avenida Del Mare, Sarasota, FL 34242
  • 5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
    /39

    $13,773

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,206 Sq Ft
    • Condo for Rent

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242

    The advertised rate of $13,773/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
  • 1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
    /54

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

    Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
  • 8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242
    8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242
    8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242
    /24

    $3,186

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,087 Sq Ft
    • Condo for Rent

    8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242

    The advertised rate of $3,186/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242
  • 1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    /28

    $7,050 Per Month

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

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

    This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
  • 5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
    /36

    $2,395 Per Month

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Condo for Rent

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242

    SIESTA KEY LIVING!! This unfurnished 2 bed/2 bath residence has a remodeled kitchen with faux granite countertops, a new microwave, dishwasher, fans throughout, tile floors throughout, and a screened porch. Enjoy the beautifully manicured 7 acres with live oaks, palm trees, tropical flowers, and flowering shrubs. A courtyard path leads to boat docks in a sheltered marina that connects to the

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
  • 1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    /45

    $9,500 Per Month

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

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

    Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
  • 212 Pass Key Rd, Siesta Key, FL 34242
    212 Pass Key Rd, Siesta Key, FL 34242
    212 Pass Key Rd, Siesta Key, FL 34242
    /21

    $2,200 Per Month

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

    212 Pass Key Rd, Siesta Key, FL 34242

    Oceanview unit in Siesta Key

    212 Pass Key Rd, Siesta Key, FL 34242
  • 9393 Midnight Pass Rd Unit P4, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit P4, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit P4, Sarasota, FL 34242
    /69

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Condo for Rent

    9393 Midnight Pass Rd Unit P4, Sarasota, FL 34242

    Enjoy awe-inspiring sunrises and sunsets from this furnished 2-bedroom, 2-bath penthouse condo at the southernmost end of Siesta Key, offered as a 3-month, 6-month, or annual rental. This corner unit offers extra windows and water views from every room, filling the space with natural light and showcasing breathtaking sunrises over Neville Preserve on Little Sarasota Bay and spectacular sunsets

    Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

    9393 Midnight Pass Rd Unit P4, Sarasota, FL 34242
  • 797 Beach Rd Unit 305, Sarasota, FL 34242
    797 Beach Rd Unit 305, Sarasota, FL 34242
    797 Beach Rd Unit 305, Sarasota, FL 34242
    /42

    Call for Price

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

    797 Beach Rd Unit 305, Sarasota, FL 34242

    Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and

    797 Beach Rd Unit 305, Sarasota, FL 34242
  • 6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
    /30

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
  • 111 Pass Key Rd, Siesta Key, FL 34242
    111 Pass Key Rd, Siesta Key, FL 34242
    111 Pass Key Rd, Siesta Key, FL 34242
    /25

    $2,500 Per Month

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

    111 Pass Key Rd, Siesta Key, FL 34242

    Siesta Key condo on Big Pass in extremely quiet complex — yet only a 5-minute walk to Siesta Village — due to a 30-day minimum rental per HOA that keeps out the short-term renters and partiers, ensuring a year-round peaceful experience!In this tree-lined “Old Florida” seaside getaway sits an updated 1 Bed 1 Bath, first floor condo, in Sandy Cove II in beautiful Sarasota, FL. A quiet and

    111 Pass Key Rd, Siesta Key, FL 34242
  • 6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    /16

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242

    Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
  • 5157 Sandy Beach Ave, Siesta Key, FL 34242
    5157 Sandy Beach Ave, Siesta Key, FL 34242
    5157 Sandy Beach Ave, Siesta Key, FL 34242
    /20

    $5,800 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft
    • House for Rent

    5157 Sandy Beach Ave, Siesta Key, FL 34242

    ANNUAL RENTAL. Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee. 4 bedrooms and 2.5 baths brings you back inside with a large open

    5157 Sandy Beach Ave, Siesta Key, FL 34242
  • 1256 Riegels Landing Dr, Sarasota, FL 34242
    1256 Riegels Landing Dr, Sarasota, FL 34242
    1256 Riegels Landing Dr, Sarasota, FL 34242
    /40

    $6,500 Per Month

    • 3 Beds
    • 4 Baths
    • 2,168 Sq Ft
    • House for Rent

    1256 Riegels Landing Dr, Sarasota, FL 34242

    This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

    Christopher Davenport STARLINK REALTY INC

    1256 Riegels Landing Dr, Sarasota, FL 34242
  • 5855 Midnight Pass Rd, Siesta Key, FL 34242
    5855 Midnight Pass Rd, Siesta Key, FL 34242
    5855 Midnight Pass Rd, Siesta Key, FL 34242
    /22

    $2,100 Per Month

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

    5855 Midnight Pass Rd, Siesta Key, FL 34242

    Do you dream of living footsteps from Siesta Key beaches all year round? Come check out this wonderful 1-bedroom and 1 bathroom furnished condo on Siesta Key with a view of the ocean. The condo located at Harbor Towers Yacht and Racquet Club has been completely updated with a new kitchen and modern theme. Enjoy your mornings looking out at the ocean from your screened-in patio. As a tenant you

    5855 Midnight Pass Rd, Siesta Key, FL 34242
  • 8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    /76

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Condo for Rent

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242

    Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks

    Erick Shumway RE/MAX ALLIANCE GROUP

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
  • 5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    /60

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
    /16

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 672 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242

    Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
  • 6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
    /25

    $12,296 Per Month

    • 2 Beds
    • 2 Baths
    • 1,319 Sq Ft
    • House for Rent

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

    Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
  • 1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
    /41

    $7,600 Per Month

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

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

    Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
  • 1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    /72

    $5,000 Per Month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242

    Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • 1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    /31

    $7,000 Per Month

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

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

    This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
  • 1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    /30

    $4,000 Per Month

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

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available through January 15, 2027 or April 2027! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
    /16

    $8,370 Per Month

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

    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242

    Villa 45 at Aloha Kai is a light-filled coastal retreat featuring an updated kitchen that perfectly complements its bright, beachy furnishings. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king bed and two twin beds, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
    /10

    $8,340 Per Month

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

    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242

    C6 is a lovely unit, has been remodeled and is awaiting your arrival. It can accommodate up to 6. The spacious living room/dining room has all new furniture, including a large couch, two recliners, coffee, and end tables. In the dining area you will find a new dining table and chairs and a ceiling fan. There is also a wall-mounted 55” UHD Smart TV. The very large Master Bedroom has a king-size

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
  • 6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242
    6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242
    6480 Midnight Pass Rd Unit 506, 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
  • 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
    /10

    $7,500 Per Month

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

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242

    This comfortable large 2 bedrooms 2 bathrooms villa is just steps away from Casa Blanca. Steps to the the white pristine beach voted #1 and the over sized pool for a cool dip. This villa comfortably sleeps up to 4 with a king size and 2 twin beds. Shopping and restaurants within steps or ride the trolley into Siesta Key Village or south to Turtle Beach. Come relax and enjoy the gulf breezes in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
    /21

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242

    Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
  • 4660 Ocean Blvd Unit N1, Sarasota, FL 34242
    4660 Ocean Blvd Unit N1, Sarasota, FL 34242
    4660 Ocean Blvd Unit N1, Sarasota, FL 34242
    /57

    $7,900 Per Month

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

    4660 Ocean Blvd Unit N1, Sarasota, FL 34242

    Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf Coast, where pristine sands meet crystal-clear waters.This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody comfort and

    Robert Bevington SHOWTIME REALTY

    4660 Ocean Blvd Unit N1, Sarasota, FL 34242

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