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 Apartment 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 11+ Guests 12+ Guests 0 Pets 1 Pets 2 Pets 3 Pets Search 1-12 of 79 results Show122436 Sort byBedrooms - Low to HighBedrooms - High to LowName - a to zName - z to aDefault (random) Favorites MAP Just Beachy at Beach Castle #16 Longboat Key, FL 2 Bdrms 2 Baths 6 Guests From $283/night incl. feesnext avail Oct 25–28 · 3-night min 5.0 View Details New Property Siesta Sunset Royale #456 Siesta Key, Florida 4 Bdrms 4 Baths 12 Guests From $1,117/night incl. feesnext avail Oct 20–22 · 2-night min View Details New Property Siesta Sunset Royale #123 Siesta Key, Florida 4 Bdrms 4 Baths 12 Guests From $1,117/night incl. feesnext avail Oct 20–22 · 2-night min View Details Serenity on Sutton Longboat Key, FL 2 Bdrms 2 Baths 4 Guests From $201/night incl. feesnext avail Nov 30 – Dec 28 · 28-night min 5.0 View Details 'Bout Time Siesta Key, Florida 2 Bdrms 2 Baths 7 Guests From $207/night incl. feesnext avail Nov 15–29 · 14-night min View Details New Property Siesta Sunset Royale #12 Siesta Key, Florida 3 Bdrms 3 Baths 10 Guests From $815/night incl. feesnext avail Oct 20–22 · 2-night min View Details Fanta Sea Sarasota, Florida 3 Bdrms 2 Baths 6 Guests From $340/night incl. feesnext avail Oct 21–24 · 3-night min 5.0 View Details New Property Poolside Paradise Sarasota, Florida 3 Bdrms 3 Baths 8 Guests From $351/night incl. feesnext avail Oct 20–23 · 3-night min View Details Siesta Bayside Bliss Siesta Key, FL 1 Bdrm 2 Baths 4 Guests From $200/night incl. feesnext avail Oct 20–27 · 7-night min 5.0 View Details Featured Property Coastal Moderne Sarasota, Florida 2 Bdrms 2 Baths 6 Guests From $268/night incl. feesnext avail Oct 20–27 · 7-night min View Details 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 New Property Windward Bay Penthouse Escape Longboat Key, Florida 2 Bdrms 2 Baths 4 Guests From $187/night incl. feesnext avail Oct 20 – Nov 17 · 28-night min View Details Search while moving Prev12345LastNext
