7 bedrooms
•
10 beds
•
8 bathrooms
•
16 guests
•
6800 sq. ft.

Saved to wishlist
Bedroom 1
1 king bed, 2 twin beds
Bedroom 2
1 king bed
Bedroom 3
1 king bunk bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
1 full bunk bed, 1 twin bunk bed, 1 twin trundle bed
Bedroom 1
1 king bed, 2 twin beds
Bedroom 2
1 king bed
Bedroom 3
1 king bunk bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
1 full bunk bed, 1 twin bunk bed, 1 twin trundle bed
Anna Maria, FL 34216, US
Anna Maria, FL, USNestled in Holmes Beach on Anna Maria Island, The Ugly Grouper is a lively outdoor eatery boasting fresh grouper tacos, burgers, and epic frozen drinks amid live music, fun games like cornhole, and a funky 3000-pound metal fish sculpture.[1][2][3][6]
Savor woodfire-grilled seafood and fresh fish tacos at Floridays Woodfire Grill & Bar or Compass Bar & Chill, where Margaritaville's frozen concoctions flow amid marina views and a breezy tropical vibe at the gateway to Anna Maria Island.
Skinny's Place is an old-school Florida beach bar from 1952, slinging award-winning juicy burgers and frosted mug beers in a rustic, open-air spot across from Manatee Public Beach. Dive into carefree island vibes with picnic tables and nostalgic charm after a sunny day out.[1][3][4]
Savor all-you-can-eat pancakes and sausage, fresh seafood platters, and gulf-front vibes at Anna Maria Island Beach Cafe, where kids play in the sand, live music plays nightly, and island-sized drinks flow from the bamboo beach bar.[1][2][3][4]
Nestled on Anna Maria Island, Ginny's & Jane E's Cafe and Gift Store blends hearty breakfasts, fresh bakery treats like monster cinnamon rolls, and an eclectic boutique of funky local art and beach treasures in a quirky, welcoming vibe.[1][2][6]
Nestled in one of Anna Maria Island's historic founding homes, The Porch Restaurant delights with scratch-made steaks, fresh seafood, and seasonal specialties amid southern charm and a breezy covered porch. Savor top-quality flavors and specialty spritzers for an unforgettable island dining escape.
Toasted Mango Cafe delights with fresh mango-infused breakfasts like award-winning waffles, French toast slathered in homemade mango butter, and creative omelets, alongside hearty lunches of blackened chicken salads and turkey burgers. This family-friendly Florida spot offers gluten-free options and old-school hospitality in a bustling, welcoming vibe.[1][3][5][7]
Sandbar Seafood + Spirits is an iconic Anna Maria Island beachfront restaurant where you can dine with your toes in the sand while enjoying fresh Gulf-to-table seafood, locally sourced vegetables from their own farm, and unforgettable sunset views of the Gulf of Mexico.
Nestled on Chicago's lakefront in Berger Park, The Waterfront Cafe offers fresh salads, seafood rolls, and sausages amid stunning skyline views and cool breezes on its garden patio. Evenings glow with twinkling lights and live jazz, blues, or classical guitar.[1][4]
Discover Robinson Preserve's transformed wetlands with 7+ miles of trails for hiking and biking, kayak adventures through mangroves spotting dolphins and manatees, and treetop canopy play for kids. Nature lovers, families, and outdoor adventurers will love its stunning views and wildlife wonders.[1][2][3]
Discover Bean Point Beach Access, the secluded northern tip of Anna Maria Island, where powdery white sands meet turquoise waters and stunning views of the Gulf, Tampa Bay, and Sunshine Skyway Bridge unfold. Nature lovers and serenity seekers will cherish this uncrowded paradise, reachable via tree-lined paths.
Discover Holmes Beach's pristine white sands and turquoise waters at Manatee Public Beach, where families thrill in jet skiing, kayaking with dolphins, and sunset cruises amid playful sea life. Perfect for adventure seekers and relaxed beach lovers craving island magic.[1][2][5][6]
Anna Maria Island is a charming Old Florida beach destination featuring pristine sugar-white sand beaches, world-class sunsets, and abundant water activities like kayaking, paddleboarding, and dolphin-spotting tours. Perfect for families and adventure seekers alike, the island offers a peaceful yet engaging escape with historic piers, local shops, and opportunities to explore mangrove ecosystems and spot wildlife.
Unleash your dog at Fort De Soto's exclusive off-leash beach—one of Florida's best with soft white sands and turquoise waters—paired with fenced Paw Playground areas for splashing and play. Perfect for pet parents seeking a pawsome paradise amid nature trails and wildlife.
Explore the historic Batteries and Military Post at Fort De Soto Park, home to the last surviving 12-inch seacoast mortars in the U.S. and immersive exhibits of Spanish-American War life. History buffs and families will love wandering these National Register-listed ruins amid stunning Gulf views.[1][3][5]
Discover the enchanting Rare Fruit Trail at Palma Sola Botanical Park, where a frost-free microclimate lets exotic gems like dragon fruit, lychee, and star fruit thrive amid butterflies and serene lakes. Nature lovers, gardeners, and families will adore this lush, free 10-acre oasis.[1][2][3]
Discover De Soto National Memorial, a hidden gem blending 16th-century explorer history with serene nature trails, ranger-led kayak tours, and living history at Camp Uzita. History buffs, families, and outdoor adventurers will love its free, uncrowded mix of education and coastal exploration.
Unwind on Anna Maria Island Beach's pristine, sugar-white sands, where calm turquoise waters invite swimming, kayaking, and dolphin spotting amid Old Florida charm. Beach lovers, families, and outdoor enthusiasts will adore this serene paradise for unforgettable sunsets and relaxation.[1][2][5]
Discover Manatee Public Beach's pristine white sands and calm Gulf waters, complete with volleyball courts, playgrounds, picnic grills, and a snack shack for all-day fun. Families, active groups, and sun-seekers will love this amenity-packed paradise on Anna Maria Island.
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
16 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Apr 14, 2026 | $1548 | Not Available |
| Apr 15, 2026 | $1598 | Not Available |
| Apr 16, 2026 | $1898 | Not Available |
| Apr 17, 2026 | $2164 | Not Available |
| Apr 18, 2026 | $2193 | Available |
| Apr 19, 2026 | $1893 | Not Available |
| Apr 20, 2026 | $1967 | Not Available |
| Apr 21, 2026 | $1842 | Not Available |
| Apr 22, 2026 | $1966 | Not Available |
| Apr 23, 2026 | $2112 | Not Available |
| Apr 24, 2026 | $1897 | Available |
| Apr 25, 2026 | $1853 | Available |
| Apr 26, 2026 | $1521 | Available |
| Apr 27, 2026 | $1439 | Available |
| Apr 28, 2026 | $1371 | Available |
| Apr 29, 2026 | $1502 | Available |
| Apr 30, 2026 | $1616 | Available |
| May 1, 2026 | $1893 | Available |
| May 2, 2026 | $2084 | Not Available |
| May 3, 2026 | $1652 | Not Available |
| May 4, 2026 | $1605 | Not Available |
| May 5, 2026 | $1549 | Not Available |
| May 6, 2026 | $1619 | Not Available |
| May 7, 2026 | $1745 | Not Available |
| May 8, 2026 | $2074 | Not Available |
| May 9, 2026 | $2083 | Not Available |
| May 10, 2026 | $1744 | Not Available |
| May 11, 2026 | $1588 | Not Available |
| May 12, 2026 | $1545 | Not Available |
| May 13, 2026 | $1612 | Not Available |
| May 14, 2026 | $1771 | Not Available |
| May 15, 2026 | $2037 | Not Available |
| May 16, 2026 | $2100 | Not Available |
| May 17, 2026 | $1908 | Not Available |
| May 18, 2026 | $1787 | Not Available |
| May 19, 2026 | $1723 | Not Available |
| May 20, 2026 | $1815 | Not Available |
| May 21, 2026 | $2118 | Not Available |
| May 22, 2026 | $2387 | Not Available |
| May 23, 2026 | $3428 | Available |
| May 24, 2026 | $3334 | Available |
| May 25, 2026 | $3106 | Available |
| May 26, 2026 | $2417 | Available |
| May 27, 2026 | $2120 | Available |
| May 28, 2026 | $2264 | Available |
| May 29, 2026 | $2388 | Available |
| May 30, 2026 | $2299 | Not Available |
| May 31, 2026 | $2164 | Not Available |
| Jun 1, 2026 | $2061 | Not Available |
| Jun 2, 2026 | $2092 | Not Available |
| Jun 3, 2026 | $2164 | Not Available |
| Jun 4, 2026 | $2253 | Not Available |
| Jun 5, 2026 | $2344 | Not Available |
| Jun 6, 2026 | $2416 | Not Available |
| Jun 7, 2026 | $2267 | Not Available |
| Jun 8, 2026 | $2151 | Not Available |
| Jun 9, 2026 | $2172 | Not Available |
| Jun 10, 2026 | $2176 | Not Available |
| Jun 11, 2026 | $3293 | Not Available |
| Jun 12, 2026 | $3758 | Not Available |
| Jun 13, 2026 | $2364 | Not Available |
| Jun 14, 2026 | $2319 | Not Available |
| Jun 15, 2026 | $2298 | Not Available |
| Jun 16, 2026 | $2241 | Not Available |
| Jun 17, 2026 | $2298 | Not Available |
| Jun 18, 2026 | $2376 | Not Available |
| Jun 19, 2026 | $2445 | Not Available |
| Jun 20, 2026 | $3117 | Available |
| Jun 21, 2026 | $3096 | Available |
| Jun 22, 2026 | $3103 | Available |
| Jun 23, 2026 | $3095 | Available |
| Jun 24, 2026 | $3101 | Available |
| Jun 25, 2026 | $3103 | Available |
| Jun 26, 2026 | $3137 | Available |
| Jun 27, 2026 | $3473 | Available |
| Jun 28, 2026 | $3460 | Available |
| Jun 29, 2026 | $3646 | Available |
| Jun 30, 2026 | $3646 | Available |
| Jul 1, 2026 | $3646 | Available |
| Jul 2, 2026 | $3646 | Not Available |
| Jul 3, 2026 | $3642 | Not Available |
| Jul 4, 2026 | $3172 | Not Available |
| Jul 5, 2026 | $3040 | Not Available |
| Jul 6, 2026 | $2365 | Not Available |
| Jul 7, 2026 | $2615 | Available |
| Jul 8, 2026 | $2650 | Available |
| Jul 9, 2026 | $2792 | Available |
| Jul 10, 2026 | $2831 | Available |
| Jul 11, 2026 | $3021 | Not Available |
| Jul 12, 2026 | $2814 | Not Available |
| Jul 13, 2026 | $2769 | Not Available |