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$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
$6,000
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
$5,500
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
$9,000
Single Family Home
345 AVENIDA LEONA, Sarasota, FL 34242
Paradise awaits in this UPDATED canal front home on Siesta Key. This 3-bedroom 2-bathroom POOL home features an open con...
Listed by ASCENDIA REAL ESTATE
$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
$3,900
Condo
1257 S PORTOFINO DR #38ALBA, Sarasota, FL 34242
DECEMBER SPECIAL *** $3,900! Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled wi...
Listed by SIGNATURE REALTY ASSOCIATES
$10,000
Condo
5760 MIDNIGHT PASS ROAD #208D, Sarasota, FL 34242
Do Not Miss This Rare Opportunity! We just had a last-minute cancellation in one of our premier communities on Siesta K...
Listed by ASCENDIA REAL ESTATE
$5,900
Condo
1660 SUMMERHOUSE LN #301, Sarasota, FL 34242
LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Sies...
Listed by JENNETTE PROPERTIES INC
$5,000
Condo
6157 MIDNIGHT PASS RD #D32, Sarasota, FL 34242
Variable rent based on season
Listed by INTEGRITY INVESTMENTS REALTY
$6,500
Condo
1250 N PORTOFINO DR #102MAR, Sarasota, FL 34242
Available January to May 1, 2025! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Har...
Listed by JUDITH GUZZI & ASSOCIATES LLC
$3,900
Condo
4660 OCEAN BLVD #B2, Sarasota, FL 34242
SIESTA KEY WATERFRONT UNIT AVAILABLE AS SHORT OR LONG TERM. Sea Village offers million dollar views and is situated on 5...
Listed by JENNETTE PROPERTIES, INC.
$30,000
Single Family Home
95 SANDY HOOK RD, Sarasota, FL 34242
6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" <br>Available NOW!!!...
Listed by COURTYARD MODERN
$8,500
Condo
5770 MIDNIGHT PASS RD #605, Sarasota, FL 34242
** BOOKED JANUARY THROUGH MARCH 2025 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY...
Listed by NEXTHOME EXCELLENCE
$7,500
Condo
460 BEACH RD #A1, Sarasota, FL 34242
Available OCT- DEC. 2024 and APR. 2025. Direct beach front condo on Siesta Key beach. This unit has it all for that Flor...
Listed by COLDWELL BANKER REALTY
$6,500
Condo
1250 N PORTOFINO DR #M301, Sarasota, FL 34242
Immaculate End Unit in the Marlin building, Ready for you to Enjoy through December 2025 and April 2026 through year-end...
Listed by JUDITH GUZZI & ASSOCIATES LLC
$7,000
Condo
1255 PEPPERTREE #201, Sarasota, FL 34242
Bayside highrise Building with underground parking, elevator, turnkey furnished, secured building, washer and dryer ni...
Listed by WATERSIDE REALTY LLC
$8,000
Condo
6415 MIDNIGHT PASS RD #602, Sarasota, FL 34242
***AVAILABLE December, 2025 through April, 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This...
Listed by AUDREY RAIN RENTALS, INC
$5,000
Condo
1257 S PORTOFINO DR #36, Sarasota, FL 34242
Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, t...
Listed by JENNETTE PROPERTIES, INC.
$6,400
Condo
1250 N PORTOFINO DR #107MAR, Sarasota, FL 34242
This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club...
Listed by JENNETTE PROPERTIES, INC.
$12,000
Single Family Home
5519 AZURE WAY, Sarasota, FL 34242
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the litt...
Listed by JENNETTE PROPERTIES, INC.
$1,290,000
Vacant Land
609 LOTUS LN, Sarasota, FL 34242
Presenting an extraordinary opportunity to build your dream estate on one of Siesta Key's desirable addresses—609 Lotus ...
Listed by PREMIER SOTHEBY'S INTERNATIONAL REALTY
$2,200,000
Vacant Land
940 SIESTA KEY PLACE PL, Sarasota, FL 34242
Paradise in North Siesta Key! <br>Discover one of the island's hidden gems — a rarely available 15,000+ SF waterfront pa...
Listed by COLDWELL BANKER REALTY