Operated by a Wander partner
Trusted operators, vetted by Wander
🌴 Topsail Cottage | Gulf Views + Walk to Crescent Beach
💖 Why You'll Love This Home
Wake up to sea breezes and panoramic Gulf views from your private rooftop crow's nest. Topsail Cottage is a luxury beach retreat where indoor-outdoor living, four private king suites, and designer touches create the perfect coastal escape.
👨👩👧 Perfect For
Couples, multi-gen families, or small groups looking for a walkable Siesta Key location with upscale amenities and beach gear included.
🎞️ Imagine This
You arrive, step inside, and feel the soft coastal breeze drift through the open living space. Your family gathers in the sunlit kitchen, laughing over fresh drinks while dinner simmers nearby. Upstairs, the rooftop crow's nest draws you up with a glass of wine in hand—where Gulf waters glisten in every direction. Later, the kids splash in the heated pool while you prep dinner on the outdoor grill station. As the sun dips below the palm trees, you realize: this is exactly how vacation should feel.
🛌 Where You'll Sleep
📍 Explore the Area
⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection, so you arrive at a pristine, hotel-quality home every time.
🔎 Need To Know: This home is located in an HOA with a shared pool. This pool is heated from November 15th to April 15th. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.
Living Room
1 queen pullout bed
Bedroom 1
1 twin sofa, 1 king bed
Bedroom 2
1 king bed, 1 twin sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Living Room
1 queen pullout bed
Bedroom 1
1 twin sofa, 1 king bed
Bedroom 2
1 king bed, 1 twin sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Siesta Key, FL 34242, US
Siesta Key, FL, USSiesta Key Oyster Bar is a lively, beachy spot known for its fresh seafood, award-winning wings, and signature tropical drinks. With dollar bills covering the ceiling and live music filling the air, it’s the perfect place to savor island flavors and soak up the local vibe.
Walt's Fish Market Restaurant in Sarasota offers the freshest seafood caught daily, served in a laid-back, tropical setting with a lively tiki bar and live music, blending a century-old family tradition with vibrant Florida coastal charm.
Connors Steak & Seafood is an upscale steakhouse offering premium aged steaks and fresh seafood grilled over wood fires, complemented by gourmet salads and pastas in a warm, elegantly appointed dining space with rich wood interiors and exceptional service.
Captain Curt's Crab & Oyster Bar offers a relaxed Old Florida vibe with fresh, wild-caught seafood, including their award-winning clam chowder, served in a spacious indoor-outdoor setting with live music and beachside charm on Siesta Key.
St. Armands Circle is a vibrant, walkable island district with upscale shops, diverse restaurants, and lush parks, perfect for anyone who loves shopping, dining, and soaking up coastal charm.
Marie Selby Botanical Gardens Downtown Sarasota offers a stunning bayfront oasis where plant lovers and families can explore vibrant tropical conservatories, a butterfly garden, and an adventurous Children's Rainforest Garden perfect for curious kids and nature enthusiasts alike.
Lido Beach offers families a perfect blend of sun, sand, and fun, with calm waters for swimming, lively sidewalk activities, and plenty of space to build sandcastles or simply relax together.
Twin Lakes Park is a vibrant 50-acre outdoor haven perfect for families and active visitors, featuring a swimming pool with water playscape, sports fields, archery range, beach area, sand volleyball courts, and a ropes course for endless fun and adventure.
Payne Park is a vibrant Sarasota destination featuring a circus-themed playground, skate park, disc golf, tennis, and scenic trails, perfect for families, outdoor enthusiasts, and anyone looking for fun in the sun.
Bayfront Park in Miami offers a vibrant waterfront escape with scenic bay views, live music, free yoga, a lively playground, and dazzling fountain shows, perfect for families, fitness lovers, and culture seekers. Its dynamic events and open green spaces make it a must-visit downtown hub.
Step into the heart of Pinecraft, where Amish and Mennonite traditions come alive in a charming, bike-friendly village. Enjoy handmade crafts, delicious home-cooked meals, and friendly locals in a relaxed, welcoming atmosphere perfect for culture seekers and curious travelers.
Soar 1,000 feet above crystal-clear Gulf waters while spotting dolphins and manatees, or zip across the Intracoastal Waterway on a jet ski—Siesta Key Watersports delivers thrilling aerial and water adventures perfect for thrill-seekers and families alike, all backed by over 28 years of safety expertise.
Historic Spanish Point offers a unique blend of archaeology, history, and nature across 30 scenic acres, perfect for history buffs, nature lovers, and families seeking a peaceful outdoor museum experience with guided tours and waterfront views.
The Sarasota Art Museum offers a vibrant cultural hub where visitors of all ages can explore world-class art exhibitions, enjoy live jazz and themed music events, participate in creative workshops, and dine at an on-site bistro—making it perfect for art enthusiasts, families, and anyone seeking an engaging cultural experience in a beautifully restored historic building.
50% refund up to 60 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
12 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 14, 2026 | $1732 | Not Available |
| Jul 15, 2026 | $1684 | Not Available |
| Jul 16, 2026 | $1684 | Not Available |
| Jul 17, 2026 | $1748 | Not Available |
| Jul 18, 2026 | $1780 | Not Available |
| Jul 19, 2026 | $1780 | Not Available |
| Jul 20, 2026 | $1796 | Not Available |
| Jul 21, 2026 | $1796 | Not Available |
| Jul 22, 2026 | $1780 | Not Available |
| Jul 23, 2026 | $1765 | Not Available |
| Jul 24, 2026 | $1717 | Not Available |
| Jul 25, 2026 | $1717 | Not Available |
| Jul 26, 2026 | $1765 | Not Available |
| Jul 27, 2026 | $1796 | Not Available |
| Jul 28, 2026 | $1811 | Not Available |
| Jul 29, 2026 | $1827 | Not Available |
| Jul 30, 2026 | $1842 | Not Available |
| Jul 31, 2026 | $1739 | Not Available |
| Aug 1, 2026 | $1680 | Available |
| Aug 2, 2026 | $1741 | Available |
| Aug 3, 2026 | $1756 | Not Available |
| Aug 4, 2026 | $1741 | Available |
| Aug 5, 2026 | $1696 | Available |
| Aug 6, 2026 | $1711 | Available |
| Aug 7, 2026 | $1741 | Not Available |
| Aug 8, 2026 | $1680 | Not Available |
| Aug 9, 2026 | $1680 | Not Available |
| Aug 10, 2026 | $1666 | Not Available |
| Aug 11, 2026 | $1608 | Not Available |
| Aug 12, 2026 | $1608 | Not Available |
| Aug 13, 2026 | $1563 | Not Available |
| Aug 14, 2026 | $1466 | Available |
| Aug 15, 2026 | $1415 | Not Available |
| Aug 16, 2026 | $1385 | Not Available |
| Aug 17, 2026 | $1370 | Not Available |
| Aug 18, 2026 | $1383 | Not Available |
| Aug 19, 2026 | $1413 | Not Available |
| Aug 20, 2026 | $1442 | Not Available |
| Aug 21, 2026 | $1413 | Not Available |
| Aug 22, 2026 | $1356 | Available |
| Aug 23, 2026 | $1328 | Available |
| Aug 24, 2026 | $1342 | Available |
| Aug 25, 2026 | $1356 | Available |
| Aug 26, 2026 | $1370 | Available |
| Aug 27, 2026 | $1383 | Available |
| Aug 28, 2026 | $1327 | Available |
| Aug 29, 2026 | $1270 | Available |
| Aug 30, 2026 | $1270 | Available |
| Aug 31, 2026 | $1283 | Available |
| Sep 1, 2026 | $1297 | Available |
| Sep 2, 2026 | $1270 | Available |
| Sep 3, 2026 | $1242 | Available |
| Sep 4, 2026 | $1168 | Available |
| Sep 5, 2026 | $1094 | Available |
| Sep 6, 2026 | $1094 | Available |
| Sep 7, 2026 | $1106 | Available |
| Sep 8, 2026 | $1130 | Available |
| Sep 9, 2026 | $1166 | Not Available |
| Sep 10, 2026 | $1190 | Not Available |
| Sep 11, 2026 | $1130 | Not Available |
| Sep 12, 2026 | $1070 | Available |
| Sep 13, 2026 | $1094 | Available |
| Sep 14, 2026 | $1106 | Available |
| Sep 15, 2026 | $1118 | Available |
| Sep 16, 2026 | $1142 | Available |
| Sep 17, 2026 | $1142 | Available |
| Sep 18, 2026 | $1142 | Available |
| Sep 19, 2026 | $1118 | Available |
| Sep 20, 2026 | $1094 | Available |
| Sep 21, 2026 | $1106 | Available |
| Sep 22, 2026 | $1118 | Available |
| Sep 23, 2026 | $1118 | Available |
| Sep 24, 2026 | $1154 | Available |
| Sep 25, 2026 | $1190 | Not Available |
| Sep 26, 2026 | $1178 | Not Available |
| Sep 27, 2026 | $1166 | Available |
| Sep 28, 2026 | $1178 | Not Available |
| Sep 29, 2026 | $1190 | Not Available |
| Sep 30, 2026 | $1190 | Not Available |
| Oct 1, 2026 | $1190 | Not Available |
| Oct 2, 2026 | $1202 | Not Available |
| Oct 3, 2026 | $1214 | Not Available |
| Oct 4, 2026 | $1178 | Not Available |
| Oct 5, 2026 | $1154 | Available |
| Oct 6, 2026 | $1166 | Available |
| Oct 7, 2026 | $1166 | Available |
| Oct 8, 2026 | $1190 | Available |
| Oct 9, 2026 | $1226 | Available |
| Oct 10, 2026 | $1226 | Available |
| Oct 11, 2026 | $1214 | Available |
| Oct 12, 2026 | $1261 | Available |