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80 reviews
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.
Pool is heated to 84 degrees in the Winter Months Only (when temperatures outside are consistently below 84 degrees).
Spa is heated 101 year-round
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.
$500 first pet, $250 each additional 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.
Anonymous
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1 week ago
Anonymous
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June 2026
Ashley S.
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October 2025
Anna Maria, Florida 34216, United States of America
Anna Maria, Florida, United States of America50% 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 |
|---|---|---|
| Oct 17, 2026 | $1479 | Not Available |
| Oct 18, 2026 | $1504 | Not Available |
| Oct 19, 2026 | $1504 | Not Available |
| Oct 20, 2026 | $1503 | Not Available |
| Oct 21, 2026 | $1504 | Not Available |
| Oct 22, 2026 | $1472 | Not Available |
| Oct 23, 2026 | $1445 | Not Available |
| Oct 24, 2026 | $1399 | Not Available |
| Oct 25, 2026 | $1363 | Not Available |
| Oct 26, 2026 | $1326 | Not Available |
| Oct 27, 2026 | $1322 | Not Available |
| Oct 28, 2026 | $1318 | Not Available |
| Oct 29, 2026 | $950 | Available |
| Oct 30, 2026 | $950 | Available |
| Oct 31, 2026 | $1345 | Not Available |
| Nov 1, 2026 | $1327 | Not Available |
| Nov 2, 2026 | $1319 | Not Available |
| Nov 3, 2026 | $1412 | Not Available |
| Nov 4, 2026 | $1456 | Not Available |
| Nov 5, 2026 | $1489 | Not Available |
| Nov 6, 2026 | $1501 | Not Available |
| Nov 7, 2026 | $1497 | Not Available |
| Nov 8, 2026 | $1404 | Not Available |
| Nov 9, 2026 | $1000 | Available |
| Nov 10, 2026 | $1000 | Available |
| Nov 11, 2026 | $1000 | Available |
| Nov 12, 2026 | $1465 | Not Available |
| Nov 13, 2026 | $1545 | Not Available |
| Nov 14, 2026 | $1604 | Not Available |
| Nov 15, 2026 | $1000 | Available |
| Nov 16, 2026 | $1000 | Available |
| Nov 17, 2026 | $1000 | Available |
| Nov 18, 2026 | $1000 | Available |
| Nov 19, 2026 | $1000 | Available |
| Nov 20, 2026 | $1000 | Available |
| Nov 21, 2026 | $1799 | Not Available |
| Nov 22, 2026 | $1985 | Not Available |
| Nov 23, 2026 | $2033 | Not Available |
| Nov 24, 2026 | $2310 | Not Available |
| Nov 25, 2026 | $2381 | Not Available |
| Nov 26, 2026 | $2288 | Not Available |
| Nov 27, 2026 | $2273 | Not Available |
| Nov 28, 2026 | $2119 | Not Available |
| Nov 29, 2026 | $1515 | Available |
| Nov 30, 2026 | $1498 | Not Available |
| Dec 1, 2026 | $1526 | Not Available |
| Dec 2, 2026 | $1410 | Not Available |
| Dec 3, 2026 | $1429 | Not Available |
| Dec 4, 2026 | $1000 | Available |
| Dec 5, 2026 | $1000 | Not Available |
| Dec 6, 2026 | $1000 | Not Available |
| Dec 7, 2026 | $1000 | Not Available |
| Dec 8, 2026 | $1000 | Not Available |
| Dec 9, 2026 | $1000 | Not Available |
| Dec 10, 2026 | $1410 | Not Available |
| Dec 11, 2026 | $1526 | Not Available |
| Dec 12, 2026 | $1592 | Not Available |
| Dec 13, 2026 | $1463 | Not Available |
| Dec 14, 2026 | $1000 | Available |
| Dec 15, 2026 | $1000 | Available |
| Dec 16, 2026 | $1000 | Available |
| Dec 17, 2026 | $1000 | Available |
| Dec 18, 2026 | $1000 | Available |
| Dec 19, 2026 | $1945 | Not Available |
| Dec 20, 2026 | $2198 | Not Available |
| Dec 21, 2026 | $2274 | Not Available |
| Dec 22, 2026 | $2346 | Not Available |
| Dec 23, 2026 | $2587 | Not Available |
| Dec 24, 2026 | $2000 | Available |
| Dec 25, 2026 | $2000 | Not Available |
| Dec 26, 2026 | $2798 | Not Available |
| Dec 27, 2026 | $3265 | Not Available |
| Dec 28, 2026 | $3343 | Not Available |
| Dec 29, 2026 | $3351 | Not Available |
| Dec 30, 2026 | $3181 | Not Available |
| Dec 31, 2026 | $3191 | Not Available |
| Jan 1, 2027 | $3040 | Not Available |
| Jan 2, 2027 | $2875 | Not Available |
| Jan 3, 2027 | $1250 | Available |
| Jan 4, 2027 | $1250 | Available |
| Jan 5, 2027 | $1250 | Available |
| Jan 6, 2027 | $1250 | Available |
| Jan 7, 2027 | $1250 | Available |
| Jan 8, 2027 | $1350 | Available |
| Jan 9, 2027 | $1350 | Available |
| Jan 10, 2027 | $1275 | Available |
| Jan 11, 2027 | $1275 | Available |
| Jan 12, 2027 | $1275 | Available |
| Jan 13, 2027 | $1275 | Available |
| Jan 14, 2027 | $1275 | Available |
| Jan 15, 2027 | $1350 | Available |