284

Newest Homes for Rent in Siesta Key, FL

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  • 60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
    /16

    $2,651

    Total Monthly Price

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

    60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242

    The advertised rate of $2,651/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 12, 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

    60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, 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
    /20

    $5,175

    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 $5,176/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

    4879 Commonwealth Dr Unit SI ID1591481P, 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
    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
  • 60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242
    /17

    $2,364

    Total Monthly Price

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

    60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242

    The advertised rate of $2,365/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

    60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242
  • 1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
    /20

    $3,996

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,001 Sq Ft
    • Condo for Rent

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242

    The advertised rate of $3,996/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 2, 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

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
  • 60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
    /15

    $2,579

    Total Monthly Price

    • Studio
    • 1 Bath
    • Condo for Rent

    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242

    The advertised rate of $2,580/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 15, 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

    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
  • 60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
    /14

    $5,292

    Total Monthly Price

    • Studio
    • 1 Bath
    • 312 Sq Ft
    • Condo for Rent

    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242

    The advertised rate of $5,292/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 2, 2027.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

    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
  • 338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
    338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
    338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
    /20

    $9,240

    Total Monthly Price

    • 3 Beds
    • 3 Baths
    • 1,732 Sq Ft
    • Condo for Rent

    338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242

    The advertised rate of $9,240/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

    338 Avenida de Paradisio Unit SI FL1-ID1590869P, 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
    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
  • 3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
    /11

    $2,500

    Total Monthly Price

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

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242

    Fully furnished, intercoastal waterfront detached garage apartment on one of the most desirable streets on far north end of Siesta Key. Could be set up as 1 or 2 bedroom. Month to month lease available, discount for longer commitments. All standard services and utilities included in rent price. Price includes one bay of a two car garage for covered parking. Unlimited pool and dock use 7a-9p

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
  • 4852 Featherbed Ln, Sarasota, FL 34242
    4852 Featherbed Ln, Sarasota, FL 34242
    4852 Featherbed Ln, Sarasota, FL 34242
    /55

    $7,000 Per Month

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

    4852 Featherbed Ln, Sarasota, FL 34242

    Welcome to your slice of paradise on Siesta Key, where island charm, relaxation, and convenience come together for the perfect beach getaway.This beautifully maintained 4-bedroom, 3-bathroom home is designed for making memories with family and friends. Spend your days lounging by the private heated saltwater pool, fire up the grill for an evening BBQ, or explore the island on the two

    Catherine Mitchell SANDRONI HOLDINGS REAL ESTATE LLC

    4852 Featherbed Ln, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    /53

    $4,000 Per Month

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

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242

    Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
  • 5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
    /24

    $5,500 Per Month

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

    5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242

    SIX+ MONTH RENTAL SPECIAL - OCTOBER 2026 THROUGH MARCH 2027, or Available for the 2027 Season. This beautifully updated 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded vacation retreat with a gorgeous view of the heated pool and ICW. Ten-minute walk or free trolley ride to the famous Siesta Key Beach. Turnkey furnished with all of the amenities you

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    5855 Midnight Pass Rd Unit 333, 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
  • 6020 Midnight Pass Rd, Sarasota, FL 34242
    6020 Midnight Pass Rd, Sarasota, FL 34242
    6020 Midnight Pass Rd, Sarasota, FL 34242
    /18

    $2,500 Per Month

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

    6020 Midnight Pass Rd, Sarasota, FL 34242

    DIRECT BEACH ACCESS! Beautifully located 1 bed/1 bath second-floor unit in the sought-after Aloha Kai community on Midnight Pass Rd, This fully furnished unit offers relaxing pool views and is move-in ready in this well-maintained beachside community. Available for 2 adults, no pets. Water and electricity included in rent. On-site parking available. Steps from the sand — perfect for tenants

    Koen Roelens ROELENS REALTY & PROPERTY MANA

    6020 Midnight Pass Rd, 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
  • 3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
    3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
    3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
    /60

    $5,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,798 Sq Ft
    • Condo for Rent

    3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242

    • UNFURNISHED • ANNUAL RENTAL ~ Rarely available in the exclusive Hamilton Club, this spacious 3-bedroom, 3.5-bath townhome offers over 4,000 square feet of space in one of Siesta Key's most desirable deep-water boating communities. A standout feature of this home is the expansive lower-level garage area, providing exceptional flexibility. In addition to the oversized two-car garage, there is a

    Tony Andrews ANDREWS & ASSOCIATES REALTY

    3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
  • 339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
    /20

    $27,156

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,711 Sq Ft
    • Condo for Rent

    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242

    The advertised rate of $27,157/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 3, 2027.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

    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
  • 5159 Oakmont Place, Sarasota, FL 34242
    5159 Oakmont Place, Sarasota, FL 34242
    5159 Oakmont Place, Sarasota, FL 34242
    /69

    $10,000 Per Month

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

    5159 Oakmont Place, Sarasota, FL 34242

    Experience the best of Siesta Key in this beautifully updated, fully furnished vacation home with a private pool, available January through March 2027 only. Beautiful resort-style living, completely renovated interiors, multiple living and dining areas, comfortably sleeps 8-10 at one of Florida's most sought-after beach destinations for the perfect coastal getaway. Inside, the open-concept layout

    Scott Nold TNG PROPERTY MANAGEMENT

    5159 Oakmont Place, 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
  • 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
  • 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
  • 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
  • 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
    /20

    $13,770

    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 $13,771/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
  • 6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
    /20

    $7,587

    Total Monthly Price

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

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242

    The advertised rate of $7,588/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

    6327 Midnight Cove Rd Unit SI ID1578382P, 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
    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
  • 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
  • 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
  • 5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
    /20

    $6,789

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,797 Sq Ft
    • Condo for Rent

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242

    The advertised rate of $6,789/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 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

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, 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
  • 1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    /87

    $7,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,467 Sq Ft
    • Condo for Rent

    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

    Waterfront Elegance at Marina Del Sol – Your Seasonal Retreat. Indulge in the ultimate Sarasota lifestyle at this stunning 3-bedroom, 2,467 sq. ft. residence in the exclusive Marina Del Sol. Thoughtfully designed and beautifully updated, this spacious condo offers the perfect balance of elegance and comfort, with three oversized porches capturing serene water views and warm coastal breezes. Step

    Olga Smith IMPERIAL PROPERTY GROUP LLC

    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
  • 1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242
    1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242
    1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242
    /20

    $5,773

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,593 Sq Ft
    • Condo for Rent

    1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242

    The advertised rate of $5,774/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

    1037 W Peppertree Dr Unit SI FL3-ID1546456P, 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
  • 6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
    /20

    $5,564

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Condo for Rent

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242

    The advertised rate of $5,564/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 18, 2027.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

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
  • 4830 Higel Ave, Sarasota, FL 34242
    4830 Higel Ave, Sarasota, FL 34242
    4830 Higel Ave, Sarasota, FL 34242
    /70

    $5,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • House for Rent

    4830 Higel Ave, Sarasota, FL 34242

    Florida charm at it’s best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the Sarasota School of Architecture. The home is on 1/3 of an acre on the Grand Canal with a dock and kidney-shaped heated pool. The new hardwood flooring and new impact windows make this home bright and inviting with volume ceiling space. The living room and kitchen offer

    toyia Youtzy JENNETTE PROPERTIES, INC.

    4830 Higel Ave, Sarasota, FL 34242
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /26

    $7,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Condo for Rent

    Unlisted Address

    FULLY FURNISHED AND INTERIOR DESIGNED 2 BEDROOM / 2 BATH UNIT now available in Harbor Towers on Siesta Key. This beautifully designed condo offers a total of 1,700 sq ft of indoor/outdoor living, including 1,152 sq ft of air-conditioned space and a spacious 540 sq ft private patio finished with travertine and turf.The unit features 9 ft ceilings, floor-to-ceiling windows, stylish

    Andres Ospina Rivera LPT REALTY, LLC

    Unlisted Address
  • 681 Avenida de Mayo, Sarasota, FL 34242
    681 Avenida de Mayo, Sarasota, FL 34242
    681 Avenida de Mayo, Sarasota, FL 34242
    /45

    $11,000 Per Month

    • 3 Beds
    • 3 Baths
    • 3,324 Sq Ft
    • House for Rent

    681 Avenida de Mayo, Sarasota, FL 34242

    Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply

    Colette Jay HORIZON REALTY INTERNATIONAL

    681 Avenida de Mayo, Sarasota, FL 34242
  • 1355 S Portofino Dr Unit 103, Sarasota, FL 34242
    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
    /73

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Condo for Rent

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242

    Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This

    Teresa Ribaudo JENNETTE PROPERTIES INC

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
  • 3939 Higel Ave, Sarasota, FL 34242
    3939 Higel Ave, Sarasota, FL 34242
    3939 Higel Ave, Sarasota, FL 34242
    /65

    $22,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,788 Sq Ft
    • House for Rent

    3939 Higel Ave, Sarasota, FL 34242

    Arrive. Unwind. Experience Siesta Key at its finest.Welcome to your private luxury retreat on Siesta Key, a modern sophisticated 4-bedroom, 4-bathroom home designed for elevated coastal living. Tucked away in one of the island’s most desirable locations, this residence offers the perfect blend of privacy, comfort, and effortless elegance.From the moment you step inside, you’re welcomed by

    Agent Photo

    Raffilena Hamilton

    GOOD LIFE REALTY LLC

    3939 Higel Ave, Sarasota, FL 34242
  • 4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    /38

    $2,800 Per Month

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

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242

    Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added

    Beth Dilley ASCENDIA REAL ESTATE

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242

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