Anna Maria, FL

Cloud Nine on Pine

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8 guests
6 bedrooms
7 bathrooms
3000 sqft

Cloud Nine on Pine by Anna Maria Island Accommodations

  • Balcony
  • Ensuite bathroom
  • Bath linens
8 guests
6 bedrooms
7 bathrooms
3000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this property

Cloud Nine on Pine by Anna Maria Island Accommodations 303 Pine Ave, Anna Maria, FL 34216 Welcome to Cloud Nine on Pine, a six bedroom, six and a half bath luxury retreat in the heart of Anna Maria Island. This coastal home features three levels of stylish living space, a rooftop deck with 360° island views, and premium amenities that include a heated pool and spa, putting green, elevator, foosball, and ping pong. Just a four-minute walk to the Gulf’s white sand beaches and steps from Pine Avenue’s shops and dining, this vacation home is the perfect choice for families and groups looking for the ultimate Anna Maria Island getaway. Highlights • 4-minute walk to Anna Maria Beach • 6 Bedrooms / 6.5 Bathrooms • 5 King beds, 1 Full-over-Twin-over-Full bunk bed • Rooftop deck with panoramic Gulf and Bay views • Private heated pool and spa • Elevator • Putting green and cornhole • Foosball, and ping pong table • 4 parking spaces • Steps from dining and shopping on Pine Avenue Soak up the sun by the heated pool and spa, craft cocktails at the outdoor wet bar, or test your skills on the putting green. Kids and adults alike will love friendly competitions at the foosball and ping pong tables. When the day winds down, head to the rooftop deck for a front-row seat to Anna Maria’s breathtaking sunsets. With an elevator for easy access and plenty of space for everyone, this home truly has it all. The second-floor great room is designed for relaxation and entertainment, with comfortable sofas, a large TV, and private terrace views. The gourmet kitchen features upgraded appliances, quartz counters, and a spacious island with barstool seating, making it easy to prepare meals together. Dine around the large family table or enjoy a breezy meal outdoors. For added convenience, this level also includes a half bath and laundry room. Cloud Nine on Pine offers six beautifully appointed bedrooms, each with its own ensuite bathroom for added privacy and comfort. On the second floor, two king bedrooms and one triple bunk bedroom (full-over-twin-over-full) provide stylish accommodations, with the bunk room being a favorite for kids. Upstairs, the third floor features three additional king bedrooms, each with spa-inspired ensuite bathrooms, walk-in showers, and some with private balconies. In total, the home features five king bedrooms and one bunk room, making it perfect for large groups and families. Room Details Second Floor -Primary Bedroom: King bed, ensuite walk-in shower -Second Bedroom: Triple bunk (Full over Twin over Full), ensuite shower -Third Bedroom: King bed, ensuite shower/tub combo Third Floor -Fourth Bedroom: King bed, ensuite shower -Fifth Bedroom: King bed, ensuite shower -Sixth Bedroom: King bed, ensuite shower Cloud Nine on Pine puts you right in the heart of Anna Maria Island. You’re within walking distance of Pine Avenue’s boutiques, ice cream shops, and restaurants, with quick access to the AMI Trolley for exploring Holmes Beach, Bradenton Beach, and beyond. Visit the Historic City Pier, enjoy local fishing, or take part in endless water adventures; everything is just minutes away. With luxurious amenities, a prime location, and plenty of room for families and groups, Cloud Nine on Pine by Anna Maria Island Accommodations is your dream vacation home. Whether you’re lounging poolside, watching sunsets from the rooftop deck, or discovering the charm of Anna Maria Island, this home makes every moment unforgettable. Book your island escape today! - There are no pets allowed in this home. *Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Accommodations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Cloud Nine on Pine by Anna Maria Island Accommodations 303 Pine Ave, Anna Maria, FL 34216 Welcome to Cloud Nine on Pine, a six bedroom, six and a half bath luxury retreat in the heart of Anna Maria Island. This coastal home features three levels of stylish living space, a rooftop deck with 360° island views, and premium amenities that include a heated pool and spa, putting green, elevator, foosball, and ping pong. Just a four-minute walk to the Gulf’s white sand beaches and steps from Pine Avenue’s shops and dining, this vacation home is the perfect choice for families and groups looking for the ultimate Anna Maria Island getaway. Highlights • 4-minute walk to Anna Maria Beach • 6 Bedrooms / 6.5 Bathrooms • 5 King beds, 1 Full-over-Twin-over-Full bunk bed • Rooftop deck with panoramic Gulf and Bay views • Private heated pool and spa • Elevator • Putting green and cornhole • Foosball, and ping pong table • 4 parking spaces • Steps from dining and shopping on Pine Avenue Soak up the sun by the heated pool and spa, craft cocktails at the outdoor wet bar, or test your skills on the putting green. Kids and adults alike will love friendly competitions at the foosball and ping pong tables. When the day winds down, head to the rooftop deck for a front-row seat to Anna Maria’s breathtaking sunsets. With an elevator for easy access and plenty of space for everyone, this home truly has it all. The second-floor great room is designed for relaxation and entertainment, with comfortable sofas, a large TV, and private terrace views. The gourmet kitchen features upgraded appliances, quartz counters, and a spacious island with barstool seating, making it easy to prepare meals together. Dine around the large family table or enjoy a breezy meal outdoors. For added convenience, this level also includes a half bath and laundry room. Cloud Nine on Pine offers six beautifully appointed bedrooms, each with its own ensuite bathroom for added privacy and comfort. On the second floor, two king bedrooms and one triple bunk bedroom (full-over-twin-over-full) provide stylish accommodations, with the bunk room being a favorite for kids. Upstairs, the third floor features three additional king bedrooms, each with spa-inspired ensuite bathrooms, walk-in showers, and some with private balconies. In total, the home features five king bedrooms and one bunk room, making it perfect for large groups and families. Room Details Second Floor -Primary Bedroom: King bed, ensuite walk-in shower -Second Bedroom: Triple bunk (Full over Twin over Full), ensuite shower -Third Bedroom: King bed, ensuite shower/tub combo Third Floor -Fourth Bedroom: King bed, ensuite shower -Fifth Bedroom: King bed, ensuite shower -Sixth Bedroom: King bed, ensuite shower Cloud Nine on Pine puts you right in the heart of Anna Maria Island. You’re within walking distance of Pine Avenue’s boutiques, ice cream shops, and restaurants, with quick access to the AMI Trolley for exploring Holmes Beach, Bradenton Beach, and beyond. Visit the Historic City Pier, enjoy local fishing, or take part in endless water adventures; everything is just minutes away. With luxurious amenities, a prime location, and plenty of room for families and groups, Cloud Nine on Pine by Anna Maria Island Accommodations is your dream vacation home. Whether you’re lounging poolside, watching sunsets from the rooftop deck, or discovering the charm of Anna Maria Island, this home makes every moment unforgettable. Book your island escape today! - There are no pets allowed in this home. *Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Accommodations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Feb 16, 2026$695Available3
Feb 17, 2026$695Available3
Feb 18, 2026$695Available3
Feb 19, 2026$695Available3
Feb 20, 2026$695Available3
Feb 21, 2026$695Not Available3
Feb 22, 2026$695Not Available3
Feb 23, 2026$695Not Available3
Feb 24, 2026$695Not Available3
Feb 25, 2026$695Not Available2
Feb 26, 2026$695Not Available2
Feb 27, 2026$695Not Available3
Feb 28, 2026$695Not Available3
Mar 1, 2026$695Not Available3
Mar 2, 2026$695Not Available3
Mar 3, 2026$695Not Available3
Mar 4, 2026$695Not Available3
Mar 5, 2026$695Not Available3
Mar 6, 2026$695Available3
Mar 7, 2026$695Available3
Mar 8, 2026$695Available3
Mar 9, 2026$695Available3
Mar 10, 2026$695Available3
Mar 11, 2026$695Not Available3
Mar 12, 2026$695Not Available3
Mar 13, 2026$695Not Available3
Mar 14, 2026$695Not Available3
Mar 15, 2026$695Available3
Mar 16, 2026$695Available3
Mar 17, 2026$695Available3
Mar 18, 2026$695Available3
Mar 19, 2026$695Available3
Mar 20, 2026$695Available3
Mar 21, 2026$695Not Available3
Mar 22, 2026$695Not Available3
Mar 23, 2026$695Not Available3
Mar 24, 2026$695Not Available3
Mar 25, 2026$695Not Available3
Mar 26, 2026$695Not Available3
Mar 27, 2026$695Not Available3
Mar 28, 2026$695Not Available3
Mar 29, 2026$695Not Available3
Mar 30, 2026$695Not Available3
Mar 31, 2026$695Not Available3
Apr 1, 2026$695Not Available3
Apr 2, 2026$695Not Available3
Apr 3, 2026$695Not Available3
Apr 4, 2026$695Not Available3
Apr 5, 2026$695Not Available3
Apr 6, 2026$695Not Available3
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Apr 11, 2026$695Not Available3
Apr 12, 2026$695Not Available3
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Apr 14, 2026$695Not Available3
Apr 15, 2026$695Not Available3
Apr 16, 2026$695Not Available3
Apr 17, 2026$695Not Available3
Apr 18, 2026$695Available3
Apr 19, 2026$695Available3
Apr 20, 2026$695Available3
Apr 21, 2026$695Available3
Apr 22, 2026$695Available3
Apr 23, 2026$695Available3
Apr 24, 2026$695Available3
Apr 25, 2026$695Available3
Apr 26, 2026$695Available3
Apr 27, 2026$695Available3
Apr 28, 2026$695Available3
Apr 29, 2026$695Available3
Apr 30, 2026$695Not Available3
May 1, 2026$695Not Available3
May 2, 2026$695Not Available3
May 3, 2026$695Not Available2
May 4, 2026$695Not Available2
May 5, 2026$695Not Available3
May 6, 2026$695Not Available3
May 7, 2026$695Not Available3
May 8, 2026$695Not Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Not Available3
May 16, 2026$695Not Available3
May 17, 2026$695Not Available3

Top notch amenities

GUEST FAVORITES

Patio
Balcony
Ensuite bathroom
Bath linens
Bed linens
Body soap
Conditioner
Shampoo
Air conditioning

Where you'll sleep



Explore Anna Maria, FL

Immerse yourself in the serene coastal rhythm of Anna Maria, where the sun-drenched shores of Anna Maria Island Beach are just steps away. Beyond the immediate sands, a short drive leads to the lush trails and scenic kayaking routes of Robinson Preserve, while Manatee Public Beach is minutes away for classic seaside relaxation. Complete your island experience with easy access to fresh seafood at Tide Tables Restaurant and Marina

Things to know

Here are some things which you should know before booking Cloud Nine on Pine

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Prime Vacations - Anna Maria’s standard cancellation policy.