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Fully Furnished Homes for Rent in Siesta Key, FL

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  • 6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    /29

    $1,943

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,108 Sq Ft
    • Condo for Rent

    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242

    The advertised rate of $1,943/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, 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
  • 6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
    /29

    $1,943

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,108 Sq Ft
    • Condo for Rent

    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242

    The advertised rate of $1,943/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    6040 E Peppertree Way Unit SI FL2-ID1591458P, 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
  • 1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    /28

    $5,867

    Total Monthly Price

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

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

    The advertised rate of $5,867/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 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

    1400 Cove II Place Unit SI FL2-ID1578373P, 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
  • 5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    /17

    $5,368

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242

    The advertised rate of $5,369/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 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

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, 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
  • 324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    /35

    $7,404

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Condo for Rent

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242

    The advertised rate of $7,404/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 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

    324 Avenida Madera Unit SI ID1578359P, 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
  • 5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
    /17

    $5,368

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242

    The advertised rate of $5,369/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 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

    5760 Midnight Pass Rd Unit SI ID1545688P, 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
  • 349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    /26

    $7,783

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242

    The advertised rate of $7,783/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, 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
  • 324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
    /35

    $7,404

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Condo for Rent

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242

    The advertised rate of $7,404/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 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

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, 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
  • 5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242
    5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242
    5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242
    /33

    $4,028

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,054 Sq Ft
    • Condo for Rent

    5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242

    The advertised rate of $4,028/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, 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
  • 1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    /34

    $11,685

    Total Monthly Price

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

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242

    The advertised rate of $11,685/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 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

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, 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
  • 349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
    /26

    $7,783

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242

    The advertised rate of $7,783/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, 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
  • 1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
    /34

    $11,685

    Total Monthly Price

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

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242

    The advertised rate of $11,685/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 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

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, 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
  • 1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
    /28

    $5,867

    Total Monthly Price

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

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

    The advertised rate of $5,867/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 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

    1400 Cove II Place Unit SI FL2-ID1578373P, 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
  • 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 29, 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
  • 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
  • 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 29, 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
  • 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
  • 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
  • 6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
    /14

    $8,970 Per Month

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

    6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242

    Find your Happy Place here in this LARGE 2 bedroom/2 bathroom, private entrance villa. There is new granite in the kitchen which is fully equipped. The master bedroom is furnished with a king size bed. The master vanity for the ladies comes with a hairdryer. The master bath features a walk-in shower with new tile and granite, all new from top to bottom. The second bedroom provides two double

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B02, 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 63, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242
    /26

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat! This inviting 1-bedroom, 1-bathroom condo is the perfect gateway to both relaxation and adventure. Prepare delicious meals in the fully equipped kitchen and enjoy them in the cozy nearby dining area. Convenience is a priority with your own private carport just steps from the door. At Casa Mar, indulge in resort-style amenities

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 63, 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
  • 1215 S Portofino Dr Unit 202, Sarasota, FL 34242
    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
    /37

    $6,500 Per Month

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

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a quick,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
  • 6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
    /9

    $6,930 Per Month

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

    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242

    Villa A18 is updated and upgraded with all the amenities to enjoy your home away from home vacation stay! Just steps to the beach voted #1 twice by Dr. Beach. This villa allows up to 6 occupants. You can also enjoy the Florida sunshine just steps away from one of the largest pools located on Siesta Key! Located on the free trolley line you can take a ride into Siesta Key village or south to

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
  • 6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
    /24

    $6,300 Per Month

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

    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242

    Starting at $210/night! Escape to coastal comfort in this charming 2-bedroom villa just steps from the beach. This beautifully furnished retreat boasts a bright and airy living space with vaulted ceilings, exposed wood beams, and abundant natural light. The open-concept living area features cozy seating, a large flat-screen TV, and stylish coastal décor that perfectly blends comfort with

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
  • 1700 Cove II Place Unit 310, Sarasota, FL 34242
    1700 Cove II Place Unit 310, Sarasota, FL 34242
    1700 Cove II Place Unit 310, Sarasota, FL 34242
    /78

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft
    • Condo for Rent

    1700 Cove II Place Unit 310, Sarasota, FL 34242

    Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Key plus taxes and fees. Live your Dream on Siesta Key for the Summer...Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the

    Robert Bevington SHOWTIME REALTY

    1700 Cove II Place Unit 310, Sarasota, FL 34242
  • 1125 W Peppertree Dr Unit 102, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 102, Sarasota, FL 34242
    1125 W Peppertree Dr Unit 102, Sarasota, FL 34242
    /37

    $10,000 Per Month

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

    1125 W Peppertree Dr Unit 102, Sarasota, FL 34242

    A 3 month stay is preferred but will accept a 2 month stay, possible 1 month. Call the office for details.Luxuriously remodeled 2 bedroom 2 full bath unit on the first floor in a gulf side high-rise building.The unit has updated wood tiles throughout, ceiling fans in each room, recessed and updated lighting.The kitchen is fully updated with stainless steel appliances, gorgeous counter

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 102, Sarasota, FL 34242

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