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473 Properties Available
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$9,350
Condo
Sarasota, FL 34242
Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Clu...
Listed by GULF COAST REALTY & MANAGEMENT
$9,300
Condo
1226 SIESTA BAYSIDE DR #1226-C, Sarasota, FL 34242
Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom...
Listed by GULF COAST REALTY & MANAGEMENT
$9,300
Condo
1241 SIESTA BAYSIDE DR #1241-A, Sarasota, FL 34242
Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dr...
Listed by GULF COAST REALTY & MANAGEMENT
$9,300
Condo
1269 SIESTA BAYSIDE DR #1269-C, Sarasota, FL 34242
Deeded Walking Access Directly to the Beach! <br> <br>New on the rental program - Beautifully updated 2-bedroom near the...
Listed by GULF COAST REALTY & MANAGEMENT
$9,300
Condo
1272 SIESTA BAYSIDE DR #1272-C, Sarasota, FL 34242
Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute...
Listed by GULF COAST REALTY & MANAGEMENT
$7,000
Condo
1360 SIESTA BAYSIDE DR #1360-D, Sarasota, FL 34242
This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retre...
Listed by GULF COAST REALTY & MANAGEMENT
$6,900
Condo
1200 SIESTA BAYSIDE DR #1200-G, Sarasota, FL 34242
Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key ...
Listed by GULF COAST REALTY & MANAGEMENT
$3,800
Condo
8911 MIDNIGHT PASS RD #514, Sarasota, FL 34242
AVAILABLE FOR SEASON 2026 $8,500/MONTH AND OFF-SEASON MONTHS 2025 AT $3,800/MONTH. UTILITIES INCLUDED. SIESTA KEY SPECTA...
Listed by JENNETTE PROPERTIES INC
$750,000
Condo
1104 S MOONMIST CT #M-10, Sarasota, FL 34242
Absolutely beautiful Villa in condominium complex, Villas are stand-alone homes with their own private yard, there are v...
Listed by BEYCOME OF FLORIDA LLC
$599,000
Condo
1046 W PEPPERTREE LN #115B, Sarasota, FL 34242
Gulfside Downstairs Garden Unit, what a wonderful location to beach and a great view overlooking one of the interior lak...
Listed by WATERSIDE REALTY LLC
$6,500
Condo
1350 N PORTOFINO DR #108TAR, Sarasota, FL 34242
Gorgeous Canal View Condo now available on Siesta Key as an annual rental. Rent for the remainder of 2025 through the W...
Listed by JUDITH GUZZI & ASSOCIATES LLC
$5,000
Condo
9122 MIDNIGHT PASS RD #34, Sarasota, FL 34242
Available May 1, 2026 for an annual lease! Rarely available 3 bed, 3 bath, plus office/work-space condo in sought-after ...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$10,000
Condo
915 SEASIDE DR #312, Weeks 32-33, Sarasota, FL 34242
Fractional Ownership. Introducing the ultimate beach ownership at The Residences on Siesta Key Beach, Hyatt Vacation Cl...
Listed by DOUGLAS ELLIMAN
$14,999
Condo
9008 MIDNIGHT PASS RD #4, Sarasota, FL 34242
THE SEA BREEZE: Exclusive seasonal rental for the discerning taste. This beautiful 3 bedroom, 3 1/2 bath residence has m...
Listed by WATERSIDE REALTY LLC
$4,000
Condo
8770 MIDNIGHT PASS RD #402B, Sarasota, FL 34242
Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location feat...
Listed by RE/MAX ALLIANCE GROUP
$3,750
Condo
8770 MIDNIGHT PASS RD #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. ...
Listed by RE/MAX ALLIANCE GROUP
$18,000
Single Family Home
345 AVENIDA LEONA, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. We...
Listed by ASCENDIA REAL ESTATE
$445,000
Condo
9011 MIDNIGHT PASS RD #228, Sarasota, FL 34242
If you love water views, this is your place! Imagine enjoying the sunrise over Little Sarasota Bay every morning from yo...
Listed by MICHAEL SAUNDERS & COMPANY
$12,000
Condo
20 WHISPERING SANDS DR #903, Sarasota, FL 34242
Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$26,319
Condo
915 SEASIDE DR #512, Sarasota, FL 34242
Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach...
Listed by GULF COAST REALTY & MANAGEMENT
$25,048
Single Family Home
1140 SEASIDE DR #101, Sarasota, FL 34242
Serenity at its finest! If luxury is calling, come indulge at the Beach House Residences for your ultimate beach vacatio...
Listed by GULF COAST REALTY & MANAGEMENT
$4,500
Condo
1257 S PORTOFINO DR #38ALBA, Sarasota, FL 34242
Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new sta...
Listed by SIGNATURE REALTY ASSOCIATES
$5,000
Condo
5760 MIDNIGHT PASS ROAD #208D, Sarasota, FL 34242
Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfron...
Listed by ASCENDIA REAL ESTATE
$5,000
Condo
6157 MIDNIGHT PASS RD #D32, Sarasota, FL 34242
Variable rent based on season
Listed by INTEGRITY INVESTMENTS REALTY
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