588 Properties Available In 34242
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$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
$15,000
Single Family Home
5516 AVENIDA DEL MARE, Sarasota, FL 34242
Welcome to Surf's Up, a modern coastal beach inspired home, where you will enjoy and marvel at the crystal-clear waters ...
Listed by ASCENDIA REAL ESTATE
$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
$6,500
Condo
1350 N PORTOFINO DR #108TAR, Sarasota, FL 34242
Gorgeous Canal View Condo now available on Siesta Key for the month of April 2024 for $5,400. Rent for the remainder of...
Listed by JUDITH GUZZI & ASSOCIATES LLC
$4,200
Condo
5855 MIDNIGHT PASS RD #426, Sarasota, FL 34242
This charming beach palace is located in the gated community of Harbor Towers on Siesta Key! Located just minutes from t...
Listed by ASCENDIA REAL ESTATE
$8,500
Condo
9122 MIDNIGHT PASS RD #34, Sarasota, FL 34242
Open for April and beyond! Rent 3 months for $8000 per month, 6 months for $7000 per month or a year for $6500! Rarely a...
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 THE SARASOTA REAL ESTATE COMP.
$7,500
Condo
116 VISTA HERMOSA CIR #210C, Sarasota, FL 34242
Experience the ultimate beach retreat firsthand! This second-floor corner unit is in the welcoming Vista Hermosa (which ...
Listed by ASCENDIA REAL ESTATE
$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