Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group needs for an unforgettable island escape — from elegant interiors to effortless beach access just moments away.
Experience luxury in our five-bedroom home, meticulously designed for comfort and enjoyment. Each of the four king suites is a sanctuary, featuring a private en-suite bathroom and a TV for your entertainment. The bunk room offers a fun and flexible space with full-over-full bunk beds, perfect for kids or additional guests. A convenient half bath is located just outside the bunk room. The gourmet chef's kitchen is equipped with a 48-inch gas range, ideal for preparing delicious meals. Enjoy outdoor dining with the gas BBQ on the pool deck. Unwind on the private covered porch with a wine cooler, offering stunning Gulf sunset views. This property provides easy beach access and is a short walk to Bean Point. The pool deck is perfect for grilling, lounging, and socializing.
Cloud 9 is ideally situated on Anna Maria Island's walkable North End, offering easy access to the beach, Bean Point, and the shops and restaurants of Pine Avenue. 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.
We give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay. For direct support, contact our office phone.
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bunk Bedroom
1 twin bunk bed
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bunk Bedroom
1 twin bunk bed
Anna Maria, Florida 34216, United States of America
Anna Maria, Florida, United States of AmericaAnna Maria Island Beach Cafe offers casual dining with stunning Gulf views, featuring all-you-can-eat pancakes and seafood specials. Enjoy live music and "Island Size" drinks at the Bamboo Beach Bar.
The Ugly Grouper offers a lively dining experience with fresh seafood and American cuisine, complemented by live music and outdoor seating. Its fun atmosphere includes games and a full bar, making it a great spot for family and friends.
Sandbar Seafood + Spirits offers fresh, locally sourced seafood and vibrant farm-to-fork dishes in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying stunning Gulf Coast sunsets.
The Waterfront Restaurant offers fresh seafood and classic American dishes in a cozy, laid-back atmosphere, complemented by its stunning waterfront location. It also features a "catch and cook" option, where they prepare your freshly caught fish.
Enjoy fresh seafood and steak at Compass Hotel's Floridays, a waterfront eatery inspired by classic Florida fish houses. The hotel also offers signature Margaritaville drinks at Compass Bar & Chill, perfect for a relaxing getaway.
The Porch Restaurant offers a refined 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.
Skinny's Place is a classic beachside eatery offering juicy burgers and crispy fries in a casual, laid-back atmosphere. This island staple has been serving up Old Florida charm since 1952.
Ginny's & Jane E's Cafe offers a blend of classic and seasonal dishes in a cozy setting, complemented by a unique gift store featuring local art and beachwear. The cafe's warm ambiance reflects "Old Florida" hospitality.
Hurricane Hanks offers fresh, high-quality American and seafood dishes in a casual, laid-back atmosphere perfect for families and sports fans alike. Enjoy flavorful burgers, seafood specialties, and strong cocktails in the heart of Holmes Beach.
Rod and Reel Pier offers a relaxed dining experience with fresh seafood and stunning views of Tampa Bay. Its quaint atmosphere and historic charm make it a beloved spot for both locals and visitors.
Explore Anna Maria Island's serene waters by paddleboarding or kayaking, perfect for beginners and nature lovers alike. Enjoy the peaceful scenery and wildlife amidst the island's mangroves.
Manatee Public Beach offers a serene escape with pristine white sands and tranquil waters, perfect for those seeking relaxation and fun activities like swimming and paddleboarding. It's ideal for families and beach lovers alike.
Anna Maria Island Beach offers serene white sands and clear waters, perfect for families and couples seeking a tranquil beach experience with opportunities for snorkeling, shelling, and sunset walks. It's ideal for those looking for a peaceful and scenic getaway.
Explore De Soto National Memorial, where history meets nature. This tranquil park offers hiking, kayaking, and living history programs, perfect for nature lovers and history enthusiasts alike.
Explore Robinson Preserve's unique blend of nature and adventure, featuring hiking trails, kayaking, and mangrove forests, perfect for outdoor enthusiasts and families. This 500-acre haven offers a serene escape from crowded beaches, ideal for those seeking a tranquil yet active experience.
Fort De Soto Dog Park and Beach offers a unique experience where dogs can play off-leash and swim, making it perfect for dog owners. The park's large fenced areas and beach access provide ample space for socialization and fun.
Holmes Beach offers a serene getaway with activities like paddleboarding and boat tours, perfect for those seeking a relaxed beach experience. It's ideal for families and adventure-seekers alike, providing a mix of leisure and exploration.
Enjoy a serene beach experience at Bean Point, where tranquil surroundings and stunning coastal views make it perfect for nature seekers and those seeking solitude. It's ideal for beachcombers and surf fishing enthusiasts alike.
Palma Sola Botanical Park offers a serene escape with its diverse tropical and temperate species, perfect for nature lovers and families. The park's unique Rare Fruit Trail and beautiful gardens make it a special destination for those seeking tranquility and botanical exploration.
Explore Fort De Soto Park's historic batteries and military post, featuring the last four surviving 12-inch seacoast mortars in the continental U.S. History buffs and nature lovers alike will enjoy this unique blend of military history and scenic Gulf views.
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.
Free cancellation up to 14 days before check-in. 50% refund up to 7 days before. 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 |
|---|---|---|
| Jun 17, 2026 | $1549 | Not Available |
| Jun 18, 2026 | $2010 | Not Available |
| Jun 19, 2026 | $2812 | Not Available |
| Jun 20, 2026 | $2756 | Not Available |
| Jun 21, 2026 | $1842 | Not Available |
| Jun 22, 2026 | $1891 | Not Available |
| Jun 23, 2026 | $1731 | Not Available |
| Jun 24, 2026 | $1740 | Not Available |
| Jun 25, 2026 | $1757 | Not Available |
| Jun 26, 2026 | $2608 | Not Available |
| Jun 27, 2026 | $1800 | Available |
| Jun 28, 2026 | $1800 | Available |
| Jun 29, 2026 | $2051 | Not Available |
| Jun 30, 2026 | $1881 | Not Available |
| Jul 1, 2026 | $2321 | Not Available |
| Jul 2, 2026 | $2724 | Not Available |
| Jul 3, 2026 | $3835 | Not Available |
| Jul 4, 2026 | $4387 | Not Available |
| Jul 5, 2026 | $3735 | Not Available |
| Jul 6, 2026 | $2462 | Not Available |
| Jul 7, 2026 | $2256 | Not Available |
| Jul 8, 2026 | $2189 | Not Available |
| Jul 9, 2026 | $2195 | Not Available |
| Jul 10, 2026 | $3016 | Not Available |
| Jul 11, 2026 | $2989 | Not Available |
| Jul 12, 2026 | $2317 | Not Available |
| Jul 13, 2026 | $2306 | Not Available |
| Jul 14, 2026 | $2126 | Not Available |
| Jul 15, 2026 | $2140 | Not Available |
| Jul 16, 2026 | $2170 | Not Available |
| Jul 17, 2026 | $3025 | Not Available |
| Jul 18, 2026 | $2875 | Not Available |
| Jul 19, 2026 | $1700 | Available |
| Jul 20, 2026 | $1700 | Available |
| Jul 21, 2026 | $1700 | Available |
| Jul 22, 2026 | $1700 | Available |
| Jul 23, 2026 | $2111 | Not Available |
| Jul 24, 2026 | $2897 | Not Available |
| Jul 25, 2026 | $2888 | Not Available |
| Jul 26, 2026 | $2266 | Not Available |
| Jul 27, 2026 | $2256 | Not Available |
| Jul 28, 2026 | $2065 | Not Available |
| Jul 29, 2026 | $2049 | Not Available |
| Jul 30, 2026 | $2046 | Not Available |
| Jul 31, 2026 | $2832 | Not Available |
| Aug 1, 2026 | $2184 | Not Available |
| Aug 2, 2026 | $1541 | Not Available |
| Aug 3, 2026 | $1518 | Not Available |
| Aug 4, 2026 | $1311 | Not Available |
| Aug 5, 2026 | $1262 | Not Available |
| Aug 6, 2026 | $1217 | Not Available |
| Aug 7, 2026 | $1982 | Not Available |
| Aug 8, 2026 | $1965 | Not Available |
| Aug 9, 2026 | $1323 | Not Available |
| Aug 10, 2026 | $1281 | Not Available |
| Aug 11, 2026 | $1200 | Not Available |
| Aug 12, 2026 | $1200 | Not Available |
| Aug 13, 2026 | $1200 | Not Available |
| Aug 14, 2026 | $1779 | Not Available |
| Aug 15, 2026 | $1787 | Not Available |
| Aug 16, 2026 | $1200 | Not Available |
| Aug 17, 2026 | $1200 | Not Available |
| Aug 18, 2026 | $1200 | Not Available |
| Aug 19, 2026 | $1200 | Not Available |
| Aug 20, 2026 | $1200 | Not Available |
| Aug 21, 2026 | $1765 | Not Available |
| Aug 22, 2026 | $1787 | Not Available |
| Aug 23, 2026 | $1800 | Available |
| Aug 24, 2026 | $1800 | Available |
| Aug 25, 2026 | $1800 | Available |
| Aug 26, 2026 | $1800 | Not Available |
| Aug 27, 2026 | $1800 | Not Available |
| Aug 28, 2026 | $1800 | Not Available |
| Aug 29, 2026 | $1800 | Not Available |
| Aug 30, 2026 | $1800 | Not Available |
| Aug 31, 2026 | $1800 | Not Available |
| Sep 1, 2026 | $1800 | Not Available |
| Sep 2, 2026 | $1800 | Not Available |
| Sep 3, 2026 | $1800 | Not Available |
| Sep 4, 2026 | $1862 | Not Available |
| Sep 5, 2026 | $1837 | Not Available |
| Sep 6, 2026 | $1427 | Not Available |
| Sep 7, 2026 | $1433 | Not Available |
| Sep 8, 2026 | $1270 | Not Available |
| Sep 9, 2026 | $1200 | Not Available |
| Sep 10, 2026 | $1200 | Not Available |
| Sep 11, 2026 | $1661 | Not Available |
| Sep 12, 2026 | $1642 | Not Available |
| Sep 13, 2026 | $1200 | Not Available |
| Sep 14, 2026 | $1600 | Available |
| Sep 15, 2026 | $1600 | Available |