5 bedrooms
•
5 beds
•
5 bathrooms
•
15 guests
•
2370 sq. ft.

Saved to wishlist
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
2 full beds
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
2 full beds
Siesta Key, FL 34242, US
Siesta Key, FL, USDry Dock Waterfront Grill is a casual waterfront dining destination on Longboat Key featuring award-winning fresh seafood, particularly its renowned grouper sandwich, with panoramic views of Sarasota Bay and both indoor and outdoor patio seating perfect for sunset dining.
Discover the freshest Gulf seafood at Crab & Fin on St. Armands Circle, a Sarasota gem since 1978 offering unique catches like Golden Tilefish and Alaskan King Crab in a welcoming island vibe.[1][6]
Discover Detwiler's Farm Market, a family-owned gem bursting with fresh produce, premium seafood, hand-cut meats, Amish-style deli delights, and farmhouse bakery treats topped off with old-fashioned ice cream. It's more than a market—it's a bustling hometown adventure that hooks you from the first visit.
Marina Jack is a premier waterfront restaurant on Sarasota Bay offering three distinct dining experiences, from the casual Blue Sunshine Patio with live music to the sophisticated Dining Room featuring award-winning wines and fresh seafood, steaks, and pasta with stunning bay views.
Connors Steak & Seafood is an upscale steakhouse specializing in premium aged steaks and fresh seafood, complemented by gourmet salads and pastas, all prepared over mesquite wood grills. With warm wood interiors, attentive service, and an inviting atmosphere, it delivers a superior dining experience perfect for both casual lunch and special occasions.
Captain Curt's Crab & Oyster Bar is a family-friendly Old Florida seafood restaurant on Siesta Key famous for its award-winning clam chowder, fresh oysters, and casual nautical atmosphere with live music and both indoor and outdoor dining.
Walt's Fish Market Restaurant is a beloved Sarasota seafood destination serving the freshest local catch since 1918, featuring fish literally caught the day you buy it, paired with a vibrant tiki bar offering live music and handcrafted cocktails in a laid-back tropical atmosphere.
Step into Florida's oldest restaurant, the Columbia in Ybor City, where five generations of family tradition deliver world-class Spanish-Cuban cuisine amid 15 vibrant dining rooms and live flamenco shows.[1][3]
Siesta Key Oyster Bar is a laid-back beachside hotspot in Siesta Key Village featuring fresh oysters, award-winning seafood, and creative cocktails in a fun Key West-style atmosphere complete with live music nightly and dollar bills decorating the walls and ceiling.
Owen's Fish Camp is a historic Sarasota seafood restaurant nestled under a century-old banyan tree, serving fresh Gulf fish and Southern classics in a casual, laid-back atmosphere with live music and a lively bar scene.
Experience the enchanting wit and romance of Lehár's The Merry Widow at the historic Sarasota Opera House, a century-old gem hosting its vibrant 2026 Winter Festival. Opera lovers and classic music fans will adore this sparkling performance in an elegantly restored venue.[1][3][4]
Discover a unique slice of Amish culture in sunny Florida at Pinecraft, where you can explore handcrafted goods, savor famous homemade pies and comfort food, and watch locals play shuffleboard and volleyball in this charming snowbird community that attracts thousands of visitors each season.
Discover St. Armands Circle, a circus-inspired island gem in Sarasota Bay boasting over 130 upscale shops, galleries, and eateries around a lush central park with statues and coastal vibes. Shopaholics, foodies, and history buffs will love its elegant European charm and walkable allure.[1][2][3]
Bayfront Park is a vibrant 32-acre waterfront escape in downtown Miami offering stunning Biscayne Bay views, unique public art installations, performance venues, and activities like flying trapeze classes and yoga—perfect for families, culture enthusiasts, and anyone seeking outdoor recreation with skyline charm.
Payne Park is a versatile 29-acre downtown Sarasota destination perfect for families and outdoor enthusiasts, featuring a circus-themed playground, skate park, tennis center, disc golf course, and scenic walking trails alongside peaceful green spaces and ponds.
Sway to live music and learn themed dance moves like jazz or salsa under the stars at Sarasota Art Museum's After Hours, blending fine art exploration with vibrant nightlife. Music lovers, dancers, and art enthusiasts will adore this monthly groove in extended gallery hours.[1][2]
Siesta Key Watersports offers thrilling parasailing, jet ski rentals, and guided dolphin tours perfect for adventure seekers of all experience levels. With over 28 years of safety expertise and USCG-certified captains, it's ideal for families and groups wanting unforgettable Gulf experiences.
Visit this iconic 26-foot sculpture depicting the famous Times Square V-J Day kiss, a powerful symbol of World War II's end that has become Sarasota's most photographed waterfront landmark. History buffs and art enthusiasts alike will appreciate this thought-provoking piece that sparks conversation about memory, celebration, and artistic interpretation.
Explore 15 acres of world-renowned botanical gardens featuring over 6,000 orchids, lush tropical conservatories, and stunning Sarasota Bay views—perfect for nature lovers, families, and anyone seeking a peaceful escape in the heart of downtown Sarasota.
Lido Beach is a pristine Gulf-front destination perfect for families seeking relaxation and adventure, offering everything from building sandcastles and swimming to paddleboarding through enchanting mangrove tunnels where you can spot dolphins, manatees, and diverse wildlife in their natural habitat.
Cancel within 24 hours for a full refund.
Pets not allowed
No smoking - fees will apply
Events require approval
Check-in after 4:00 pm
Check-out before 10:00 am
15 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Apr 15, 2026 | $773 | Available |
| Apr 16, 2026 | $773 | Not Available |
| Apr 17, 2026 | $988 | Not Available |
| Apr 18, 2026 | $975 | Not Available |
| Apr 19, 2026 | $773 | Not Available |
| Apr 20, 2026 | $773 | Available |
| Apr 21, 2026 | $773 | Available |
| Apr 22, 2026 | $786 | Not Available |
| Apr 23, 2026 | $965 | Not Available |
| Apr 24, 2026 | $1157 | Not Available |
| Apr 25, 2026 | $1171 | Not Available |
| Apr 26, 2026 | $795 | Not Available |
| Apr 27, 2026 | $773 | Available |
| Apr 28, 2026 | $773 | Available |
| Apr 29, 2026 | $862 | Not Available |
| Apr 30, 2026 | $930 | Not Available |
| May 1, 2026 | $1037 | Not Available |
| May 2, 2026 | $1031 | Not Available |
| May 3, 2026 | $783 | Available |
| May 4, 2026 | $773 | Available |
| May 5, 2026 | $1057 | Available |
| May 6, 2026 | $1059 | Not Available |
| May 7, 2026 | $1087 | Not Available |
| May 8, 2026 | $985 | Not Available |
| May 9, 2026 | $942 | Available |
| May 10, 2026 | $773 | Not Available |
| May 11, 2026 | $773 | Not Available |
| May 12, 2026 | $773 | Not Available |
| May 13, 2026 | $773 | Not Available |
| May 14, 2026 | $947 | Not Available |
| May 15, 2026 | $1011 | Not Available |
| May 16, 2026 | $1017 | Not Available |
| May 17, 2026 | $926 | Not Available |
| May 18, 2026 | $858 | Not Available |
| May 19, 2026 | $838 | Not Available |
| May 20, 2026 | $874 | Not Available |
| May 21, 2026 | $1007 | Not Available |
| May 22, 2026 | $1247 | Not Available |
| May 23, 2026 | $1240 | Available |
| May 24, 2026 | $1231 | Not Available |
| May 25, 2026 | $1022 | Not Available |
| May 26, 2026 | $999 | Not Available |
| May 27, 2026 | $773 | Not Available |
| May 28, 2026 | $848 | Not Available |
| May 29, 2026 | $894 | Not Available |
| May 30, 2026 | $1045 | Not Available |
| May 31, 2026 | $942 | Available |
| Jun 1, 2026 | $1034 | Not Available |
| Jun 2, 2026 | $975 | Not Available |
| Jun 3, 2026 | $1108 | Not Available |
| Jun 4, 2026 | $1190 | Not Available |
| Jun 5, 2026 | $1622 | Not Available |
| Jun 6, 2026 | $1360 | Available |
| Jun 7, 2026 | $1273 | Available |
| Jun 8, 2026 | $1064 | Available |
| Jun 9, 2026 | $1210 | Available |
| Jun 10, 2026 | $1216 | Available |
| Jun 11, 2026 | $1232 | Available |
| Jun 12, 2026 | $1442 | Available |
| Jun 13, 2026 | $1885 | Not Available |
| Jun 14, 2026 | $1330 | Not Available |
| Jun 15, 2026 | $1231 | Not Available |
| Jun 16, 2026 | $1265 | Not Available |
| Jun 17, 2026 | $1291 | Not Available |
| Jun 18, 2026 | $1376 | Not Available |
| Jun 19, 2026 | $1484 | Not Available |
| Jun 20, 2026 | $1436 | Not Available |
| Jun 21, 2026 | $1238 | Not Available |
| Jun 22, 2026 | $1147 | Not Available |
| Jun 23, 2026 | $1161 | Not Available |
| Jun 24, 2026 | $1439 | Not Available |
| Jun 25, 2026 | $1439 | Not Available |
| Jun 26, 2026 | $1586 | Not Available |
| Jun 27, 2026 | $1422 | Available |
| Jun 28, 2026 | $1190 | Available |
| Jun 29, 2026 | $1190 | Available |
| Jun 30, 2026 | $1190 | Available |
| Jul 1, 2026 | $1671 | Available |
| Jul 2, 2026 | $2029 | Available |
| Jul 3, 2026 | $2029 | Available |
| Jul 4, 2026 | $2050 | Available |
| Jul 5, 2026 | $1411 | Available |
| Jul 6, 2026 | $1238 | Available |
| Jul 7, 2026 | $1238 | Available |
| Jul 8, 2026 | $1238 | Available |
| Jul 9, 2026 | $1238 | Available |
| Jul 10, 2026 | $1389 | Available |
| Jul 11, 2026 | $1344 | Not Available |
| Jul 12, 2026 | $1161 | Not Available |
| Jul 13, 2026 | $1161 | Not Available |
| Jul 14, 2026 | $1160 | Not Available |