$0
for 0 nights

Home in Anna Maria, Florida

5 bedrooms

0 beds

5 bathrooms

8 guests

1000 sq. ft.

Luxury

Elevated properties with standout design

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

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.

Where you’ll sleep

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

Amenities

Common Amenities

  • Sound system
  • Beach essentials
  • Long term stays allowed
  • Elevator
  • Wifi
  • Garage
  • Luggage drop off allowed
  • Free parking
  • Beachfront
  • Bicycle
  • Wine Cellar
  • Pet relief area
  • Balcony
  • Water slide
  • Hike trail nearby
  • Boat
  • Bay views
  • Private Chef
  • Fishing Area
  • Golf Course
  • Beach access
  • Hot water
  • Fire extinguisher
  • Air conditioning
  • Smoke detector
  • First aid kit
  • Kitchen
  • Fire place
  • Heating
  • Iron
  • Patio
  • Waterfront
  • Ocean view
  • Carbon monoxide detector
  • Hangers
  • Dedicated workspace
  • Crib
  • Garden
  • High chair
  • Extra pillows
  • Ice maker
  • Stair gate
  • Board games
  • Baking sheet
  • Mini fridge
  • Safe
  • Toys
  • Closet
  • Beach
  • Beach View
  • Children’s dinnerware
  • Cleaning Disinfection
  • Cleaning products
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fishing
  • Golf - Optional
  • High touch surfaces disinfected
  • Horseback Riding
  • Pets allowed
  • Private entrance
  • Shopping
  • Spa
  • Suitable for children (2-12 years)
  • Suitable for events
  • Suitable for infants (under 2 years)
  • Water Sports
  • Water View
  • Gym
  • Tennis court
  • Children dinnerware
  • Pack n play
  • Books
  • Basketball Court
  • Massage table
  • Heated pool
  • Laundromat nearby
  • Ironing board
  • Bedroom door lock

Pool

  • Outdoor pool
  • Hot tub

Patio

  • Outdoor seating
  • Outdoor dining area
  • Ceiling fan
  • TV
  • BBQ Area
  • BBQ Utensils
  • Paddle board
  • Kayaks
  • Cornhole

Balcony 1

  • Outdoor seating

Balcony 2

  • Outdoor seating

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Cooking basics
  • Coffee
  • Blender
  • Coffee maker
  • Dishwasher
  • Fridge
  • Kettle
  • Microwave
  • Freezer
  • Oven
  • Pots and pans
  • Spices
  • Stove
  • Tea
  • Toaster
  • Wine glasses
  • Dishes
  • Silverware

Common Area

  • Coffee maker
  • Coffee
  • Kitchenette

Bedroom 1

  • Bed linens

Ensuite Bathroom 1

  • Bath linens
  • Ensuite bathroom
  • Body soap
  • Shampoo
  • Shower gel
  • Shower
  • Conditioner
  • Toilet
  • Hair dryer
  • Bathtub

Bedroom 2

  • TV
  • Bed linens

Ensuite Bathroom 2

  • Bath linens
  • Body soap
  • Ensuite bathroom
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet

Bedroom 3

  • Bed linens
  • TV

Ensuite Bathroom 3

  • Bath linens
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Ensuite bathroom
  • Toilet

Bedroom 4

  • TV
  • Bed linens

Ensuite Bathroom 4

  • Bath linens
  • Ensuite bathroom
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet

Bunk Bedroom

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 5

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Body soap

Half Bath 1

  • Bath linens
  • Body soap
  • Half bath
  • Toilet

Half Bath 2

  • Bath linens
  • Half bath
  • Toilet
  • Body soap

Laundry Room

  • Washer
  • Dryer
  • Cleaning supplies

4.9 · 78 reviews

A

Anonymous

June 2026

We had a wonderful stay, the house is beautiful, and the views are unmatched. The layout was perfect for our group, and we enjoyed the pool and views from every deck. The kitchen was well stocked; we had everything we needed. The golf cart and bikes were a great addition; we used them daily. We will definitely be back.
A

Ashley S.

October 2025

The view; impeccable. The golf cart was such a great thing to have access too. House was clean. The company who runs this house was so responsive. We had one issue with a grill and within 24 hours we had a new one. Everything we needed we had access to. Garage was stocked with beach chairs. Just fyi…the house next door is under construction and they start banging around 7am. Makes it not so relaxing sitting poolside or sleeping past 7am. Probably another month of construction. Sunrises were so beautiful. Once construction is done, which is by no means something this house can prevent, this place would be top notch. The family had a wonderful time.
A

Ashley

October 2025

The view; impeccable. The golf cart was such a great thing to have access too. House was clean. The company who runs this house was so responsive. We had one issue with a grill and within 24 hours we had a new one. Everything we needed we had access to. Garage was stocked with beach chairs. Just fyi…the house next door is under construction and they start banging around 7am. Makes it not so relaxing sitting poolside or sleeping past 7am. Probably another month of construction. Sunrises were so beautiful. Once construction is done, which is by no means something this house can prevent, this place would be top notch. The family had a wonderful time.

Where you’ll be

Anna Maria, Florida 34216, United States of America

Anna Maria, Florida, United States of America
27.53618622-82.73771667
Timezone: America/New_York

Restaurants

Rod and Reel Pier

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.

Anna Maria Island Beach Cafe

Anna 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

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

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

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.

Compass Hotel Anna Maria Sound by Margaritaville

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 Anna Maria

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 inc.

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 and Gift Store

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

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.

Attractions

Ana Maria island

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

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

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.

De Soto National Memorial

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.

Robinson Preserve

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 / Beach

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

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.

Bean Point Beach Access

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

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.

Fort De Soto Park Batteries And Military Post

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.

Beach N Rides

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.

Coconut Rentals

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.

Things to know

Cancellation policy

50% refund up to 60 days before check-in. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Sep 2, 2026$1368Not Available
Sep 3, 2026$1368Not Available
Sep 4, 2026$1519Not Available
Sep 5, 2026$1614Not Available
Sep 6, 2026$1586Not Available
Sep 7, 2026$1368Not Available
Sep 8, 2026$1368Not Available
Sep 9, 2026$1368Not Available
Sep 10, 2026$1368Not Available
Sep 11, 2026$1380Not Available
Sep 12, 2026$1385Not Available
Sep 13, 2026$1368Not Available
Sep 14, 2026$1250Available
Sep 15, 2026$1250Available
Sep 16, 2026$1250Available
Sep 17, 2026$1250Available
Sep 18, 2026$1250Available
Sep 19, 2026$1368Not Available
Sep 20, 2026$1368Not Available
Sep 21, 2026$1368Not Available
Sep 22, 2026$1368Not Available
Sep 23, 2026$1368Not Available
Sep 24, 2026$1368Not Available
Sep 25, 2026$1368Not Available
Sep 26, 2026$1250Available
Sep 27, 2026$1250Available
Sep 28, 2026$1250Available
Sep 29, 2026$1250Available
Sep 30, 2026$1250Available
Oct 1, 2026$1250Available
Oct 2, 2026$1250Available
Oct 3, 2026$1456Not Available
Oct 4, 2026$1407Not Available
Oct 5, 2026$1440Not Available
Oct 6, 2026$1471Not Available
Oct 7, 2026$1437Not Available
Oct 8, 2026$1499Not Available
Oct 9, 2026$1593Not Available
Oct 10, 2026$1604Not Available
Oct 11, 2026$1591Not Available
Oct 12, 2026$1541Not Available
Oct 13, 2026$1540Not Available
Oct 14, 2026$1541Not Available
Oct 15, 2026$1545Not Available
Oct 16, 2026$1551Not Available
Oct 17, 2026$1517Not Available
Oct 18, 2026$1539Not Available
Oct 19, 2026$1539Not Available
Oct 20, 2026$1538Not Available
Oct 21, 2026$1540Not Available
Oct 22, 2026$1540Not Available
Oct 23, 2026$1512Available
Oct 24, 2026$1430Available
Oct 25, 2026$1391Available
Oct 26, 2026$1368Available
Oct 27, 2026$1368Available
Oct 28, 2026$1368Available
Oct 29, 2026$1368Available
Oct 30, 2026$1368Available
Oct 31, 2026$1368Not Available
Nov 1, 2026$1383Not Available
Nov 2, 2026$1374Not Available
Nov 3, 2026$1385Not Available
Nov 4, 2026$1530Not Available
Nov 5, 2026$1552Not Available
Nov 6, 2026$1558Not Available
Nov 7, 2026$1551Not Available
Nov 8, 2026$1467Not Available
Nov 9, 2026$1413Available
Nov 10, 2026$1470Available
Nov 11, 2026$1483Available
Nov 12, 2026$1540Not Available
Nov 13, 2026$1578Not Available
Nov 14, 2026$1642Not Available
Nov 15, 2026$1594Available
Nov 16, 2026$1574Available
Nov 17, 2026$1580Available
Nov 18, 2026$1477Available
Nov 19, 2026$1546Available
Nov 20, 2026$1663Available
Nov 21, 2026$1849Not Available
Nov 22, 2026$2095Not Available
Nov 23, 2026$2097Not Available
Nov 24, 2026$2286Not Available
Nov 25, 2026$2361Not Available
Nov 26, 2026$2315Not Available
Nov 27, 2026$2270Not Available
Nov 28, 2026$2162Not Available
Nov 29, 2026$1531Available
Nov 30, 2026$1516Not Available
Dec 1, 2026$1548Not Available