Search Results Filters Filters Bedrooms 0 + 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + Bathrooms 0 + 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + Clear Filters Amenities Beach Access Beachfront Concierge - Available Laptop Friendly Workspace Pool Tennis Court - Community View - Beach View - Water Washer - Private Wifi Pet Friendly Type Condo House Studio Townhouse Villa Apply Filters Where SkyRun Sarasota Florida Greater Sarasota Area Downtown Sarasota Lido Key Longboat Key Beach Castle Parking Sarasota Metro Area Siesta Key - People 2+ Guests 3+ Guests 4+ Guests 5+ Guests 6+ Guests 7+ Guests 8+ Guests 9+ Guests 10+ Guests 0 Pets 1 Pets 2 Pets 3 Pets Search 1-11 of 65 results Show122436 Sort byBedrooms - Low to HighBedrooms - High to LowName - a to zName - z to aDefault (random) Favorites MAP Featured Property Uptown Oasis Sarasota, FL 3 Bdrms 3 Baths 8 Guests From $731/night incl. feesnext avail Jan 30 – Feb 6, 2027 · 7-night min View Details Serenity on Sutton Longboat Key, FL 2 Bdrms 2 Baths 4 Guests From $212/night incl. feesnext avail Nov 30 – Dec 28 · 28-night min 5.0 View Details Featured Property It's a Shore Thing at Beach Castle #14 Longboat Key, FL 1 Bdrm 1 Baths 4 Guests From $280/night incl. feesnext avail Sep 26–28 · 2-night min 4.8 View Details Just Beachy at Beach Castle #16 Longboat Key, FL 2 Bdrms 2 Baths 6 Guests From $283/night incl. feesnext avail Sep 26–29 · 3-night min 5.0 View Details Buttonwood Bliss Longboat Key, FL 2 Bdrms 2 Baths 4 Guests From $209/night incl. feesnext avail Sep 28 – Oct 12 · 14-night min 5.0 View Details Featured Property The Windward House Siesta Key, FL 3 Bdrms 2 Baths 6 Guests From $547/night incl. feesnext avail Oct 4–8 · 4-night min 5.0 View Details Sea La Vie Siesta Key, FL 3 Bdrms 2 Baths 9 Guests 5.0 View Details Bayside Hideaway at Beach Castle #27 Longboat Key, FL 3 Bdrms 3 Baths 8 Guests From $608/night incl. feesnext avail Sep 26–28 · 2-night min View Details New Property Papaya Place Sarasota, Florida 2 Bdrms 2 Baths 6 Guests From $278/night incl. feesnext avail Sep 30 – Oct 7 · 7-night min View Details Uptown Luxury on Audubon Sarasota, FL 4 Bdrms 3 Baths 10 Guests From $512/night incl. feesnext avail Sep 27 – Oct 2 · 5-night min 5.0 View Details Featured Property Siesta Treasure #4 Siesta Key, Florida 2 Bdrms 1 Baths 4 Guests From $358/night incl. feesnext avail Sep 25–28 · 3-night min View Details Search while moving Prev12345LastNext
