Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity Gulf is your private beachfront sanctuary on the coveted north end—where relaxed bohemian style meets unforgettable Gulf views.
Just completed: a stunning beachside heated pool, perfectly positioned for sun-soaked afternoons and sunset swims with the Gulf as your backdrop.
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Thoughtfully refreshed with all-new flooring and a beautifully redesigned kitchen with brand-new appliances, this home blends comfort, style, and effortless coastal living. The bright, airy interior draws your eyes straight through sliding glass doors to the turquoise waters beyond
Direct beach access just steps away
NEW heated beachfront pool + hot tub
Paddle boards, kayaks & bikes included for guest use
Complimentary 6-passenger golf cart for easy island exploring
Serendipity Gulfront provides a complimentary 6-passenger Golf Cart, perfect for exploring the island. For exploring further, the free island trolley provides convenient transportation, with a stop located right on Pine Ave. Free parking is available on the premises and on the street. The closest major airport is approximately a 1-hour drive away.
Please review and agree to the Reservation Agreement.
Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire.
Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval.
Pet Fee and Pet Waiver Required. $300 per pet
Any unauthorized pets= 25% surcharge
Traveler must provide photo ID and guest list If for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.)
Due to the extensive equipment provided at the home, there are additional documents required.
The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+
All Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.
Anna Maria, Florida 34216, US
Anna Maria, Florida, USThe Ugly Grouper offers a lively dining experience with fresh seafood, American favorites, and a vibrant atmosphere featuring live music and outdoor seating. Enjoy a relaxed meal amidst a fun, laid-back setting on Anna Maria Island.
Anna Maria Island Beach Cafe offers casual dining with stunning Gulf views, featuring all-you-can-eat pancakes and Friday fish fries. Enjoy live music and beach activities alongside delicious meals.
Sandbar Seafood + Spirits offers fresh Gulf-to-table seafood and local organic dishes in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying breathtaking sunsets over the Gulf of Mexico. Perfect for casual meals, sunset cocktails, and soaking up Old Florida charm.
The Waterfront Restaurant offers a blend of fresh seafood and upscale dining with stunning views. Its welcoming atmosphere and diverse menu make it a perfect spot for both casual and special occasions.
Compass Hotel Anna Maria Sound offers a vibrant dining experience with Floridays Woodfire Grill & Bar, serving fresh seafood in a casual waterfront setting, and Compass Bar & Chill, featuring signature Margaritaville drinks. The hotel's tropical ambiance complements its delicious cuisine.
Rod and Reel Pier offers a charming, laid-back dining experience perched over Tampa Bay, serving fresh seafood and casual fare with stunning water views and a glimpse of local fishing life. Its cozy atmosphere and historic pier setting make it a beloved spot on Anna Maria Island.
Ginny's & Jane E's Cafe offers a blend of delicious breakfast and lunch options, complemented by a unique gift store filled with local art and quirky souvenirs. This charming spot embodies the warm hospitality of "Old Florida" in a historic setting.
Skinny's Place is a classic beachside eatery offering juicy burgers and crispy fries in a casual, Old Florida setting. It's a rustic spot perfect for a laid-back meal near the beach.
The Porch Restaurant offers a sophisticated dining experience with top-quality steak, fresh fish, and seasonal entrées, set within a historic home on Anna Maria Island. Its intimate ambiance and extensive wine selection make it a sought-after destination for special occasions.
Hurricane Hanks offers a casual, island-style dining experience with a focus on fresh seafood and classic American fare. The restaurant provides a laid-back atmosphere perfect for enjoying great food and drinks in the heart of Holmes Beach.
A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Beach N Rides at 941-251-7916. Use the discount code: Serendipity at checkout to receive your special rate.
A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Coconut Rentals at 941-269-1080. Use the discount code: Serendipity at checkout to receive your special rate.
Explore Anna Maria Island's serene beaches and tranquil waters, perfect for swimming and water activities. Nature lovers and families will enjoy the island's peaceful atmosphere and diverse wildlife.
Manatee Public Beach offers a serene escape with pristine white sand, calm Gulf waters, and activities like swimming and paddleboarding. It's perfect for families and those seeking relaxation and recreation in a beautiful coastal setting.
Experience the serene beauty of Holmes Beach, where you can relax on sandy shores, enjoy water sports, and soak up the Florida sun. It's perfect for families and beach lovers seeking a tranquil getaway.
Anna Maria Island Beach offers serene white sands and clear, warm Gulf waters perfect for swimming, shelling, and dolphin watching, making it ideal for families, nature lovers, and anyone seeking a peaceful beach escape. Its tranquil vibe and stunning sunsets create unforgettable moments.
Explore Robinson Preserve, a 600-acre haven offering hiking, kayaking, and bird-watching amidst mangroves and scenic waterways. Nature lovers and outdoor enthusiasts will delight in its diverse ecosystems and panoramic views.
Fort De Soto Dog Park and Beach offers a unique experience for pet owners, allowing dogs to play and swim freely in a designated beach area. It's perfect for those seeking a fun, social outing with their furry friends.
De Soto National Memorial offers a blend of history and nature, perfect for those who enjoy hiking, kayaking, and exploring historical sites. It's ideal for families and nature enthusiasts seeking a mix of adventure and educational experiences.
Bean Point Beach is a secluded gem on Anna Maria Island, offering serene views and tranquil waters perfect for those seeking a peaceful escape. Locals and nature lovers alike enjoy its stunning sunsets and pristine sand.
Palma Sola Botanical Park offers a peaceful stroll through lush gardens featuring rare tropical fruits, vibrant butterfly habitats, and themed plant collections—perfect for nature lovers, families, and anyone seeking a serene outdoor escape.
Explore historic Fort De Soto Park, featuring the last four surviving 12-inch seacoast mortars in the continental U.S. and offering a glimpse into military history and stunning Gulf views. This site is perfect for history buffs and nature lovers alike.
50% refund up to 60 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 17, 2026 | $1200 | Not Available |
| Jul 18, 2026 | $1200 | Not Available |
| Jul 19, 2026 | $1354 | Not Available |
| Jul 20, 2026 | $1388 | Not Available |
| Jul 21, 2026 | $1303 | Not Available |
| Jul 22, 2026 | $1356 | Not Available |
| Jul 23, 2026 | $1399 | Not Available |
| Jul 24, 2026 | $1600 | Not Available |
| Jul 25, 2026 | $1600 | Not Available |
| Jul 26, 2026 | $1600 | Not Available |
| Jul 27, 2026 | $1600 | Not Available |
| Jul 28, 2026 | $1600 | Not Available |
| Jul 29, 2026 | $1100 | Available |
| Jul 30, 2026 | $1100 | Available |
| Jul 31, 2026 | $1100 | Available |
| Aug 1, 2026 | $1992 | Not Available |
| Aug 2, 2026 | $1428 | Not Available |
| Aug 3, 2026 | $1289 | Not Available |
| Aug 4, 2026 | $1193 | Not Available |
| Aug 5, 2026 | $1160 | Not Available |
| Aug 6, 2026 | $1060 | Not Available |
| Aug 7, 2026 | $1750 | Not Available |
| Aug 8, 2026 | $1100 | Available |
| Aug 9, 2026 | $1100 | Available |
| Aug 10, 2026 | $1000 | Not Available |
| Aug 11, 2026 | $1000 | Not Available |
| Aug 12, 2026 | $1000 | Not Available |
| Aug 13, 2026 | $1000 | Not Available |
| Aug 14, 2026 | $1648 | Available |
| Aug 15, 2026 | $1589 | Available |
| Aug 16, 2026 | $900 | Available |
| Aug 17, 2026 | $900 | Available |
| Aug 18, 2026 | $900 | Available |
| Aug 19, 2026 | $900 | Available |
| Aug 20, 2026 | $900 | Available |
| Aug 21, 2026 | $1569 | Available |
| Aug 22, 2026 | $1582 | Available |
| Aug 23, 2026 | $1042 | Available |
| Aug 24, 2026 | $1040 | Available |
| Aug 25, 2026 | $900 | Available |
| Aug 26, 2026 | $917 | Available |
| Aug 27, 2026 | $930 | Available |
| Aug 28, 2026 | $1643 | Available |
| Aug 29, 2026 | $1653 | Available |
| Aug 30, 2026 | $1125 | Available |
| Aug 31, 2026 | $1117 | Available |
| Sep 1, 2026 | $944 | Available |
| Sep 2, 2026 | $927 | Available |
| Sep 3, 2026 | $921 | Available |
| Sep 4, 2026 | $1756 | Available |
| Sep 5, 2026 | $1732 | Available |
| Sep 6, 2026 | $1381 | Available |
| Sep 7, 2026 | $1386 | Available |
| Sep 8, 2026 | $1250 | Available |
| Sep 9, 2026 | $869 | Available |
| Sep 10, 2026 | $800 | Not Available |
| Sep 11, 2026 | $1432 | Not Available |
| Sep 12, 2026 | $1425 | Not Available |
| Sep 13, 2026 | $919 | Available |
| Sep 14, 2026 | $883 | Available |
| Sep 15, 2026 | $800 | Available |
| Sep 16, 2026 | $800 | Available |
| Sep 17, 2026 | $800 | Available |
| Sep 18, 2026 | $1272 | Available |
| Sep 19, 2026 | $1261 | Available |
| Sep 20, 2026 | $814 | Available |
| Sep 21, 2026 | $826 | Available |
| Sep 22, 2026 | $800 | Available |
| Sep 23, 2026 | $800 | Available |
| Sep 24, 2026 | $800 | Available |
| Sep 25, 2026 | $1312 | Available |
| Sep 26, 2026 | $1317 | Available |
| Sep 27, 2026 | $875 | Available |
| Sep 28, 2026 | $880 | Available |
| Sep 29, 2026 | $800 | Available |
| Sep 30, 2026 | $800 | Available |
| Oct 1, 2026 | $800 | Available |
| Oct 2, 2026 | $1350 | Available |
| Oct 3, 2026 | $1346 | Available |
| Oct 4, 2026 | $904 | Available |
| Oct 5, 2026 | $896 | Available |
| Oct 6, 2026 | $800 | Available |
| Oct 7, 2026 | $800 | Available |
| Oct 8, 2026 | $800 | Available |
| Oct 9, 2026 | $1515 | Available |
| Oct 10, 2026 | $1511 | Available |
| Oct 11, 2026 | $1398 | Available |
| Oct 12, 2026 | $1393 | Available |
| Oct 13, 2026 | $1260 | Available |
| Oct 14, 2026 | $896 | Available |
| Oct 15, 2026 | $965 | Available |