SKY on Anna Maria

Welcome to your very own piece of luxury! Floor-to-ceiling windows, a backyard oasis, and the beach across the street. What more could you want? With two bedrooms plus a den, two bathrooms, and an elevator to the main level of the house, relaxation is accessible for everyone. While you and your party are inside the house, you can cook a delicious meal while gazing out the windows at a beautiful sky view. After dinner, grab a drink and cozy up around the stunning indoor fireplace as you take in the statement pieces that fill the home. The ambiance doesn’t stop indoors, though. 

When you walk out into the backyard, you will be transported into your own zen oasis. A lush variety of trees provide shade for you and your group as you gather around in the Adirondack chairs. And just across the street… the beach awaits. Come with as little as yourself and a towel, or bring one of the available paddleboards to explore the ocean. Itching to explore more? Grab one of the bikes and take a ride around Anna Maria Island’s 7 miles. 

SKY offers you a prime location for all that Anna Maria Island has to offer. During your stay, you can explore the pier and drive down to Pine Avenue, where award-winning restaurants and local shops wait for you. When you’re done exploring, though, you’ll have the delight of coming back home to SKY - your dream luxury retreat. 

Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

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8 Occupants 2 Bedrooms 2 Bathrooms


  • Internet
  • Wireless
  • Air conditioning
  • Kitchen
  • Gym
  • Fireplace
  • Washing Machine
  • Dryer
  • Elevator
  • 24-hour checkin
  • Hair Dryer
  • Heating
  • Smoke detector
  • Carbon Monoxide Detector
  • First aid kit
  • Fire Extinguisher
  • Essentials
  • Shampoo
  • Hangers
  • Iron
  • Laptop Friendly workspace
  • TV
  • Pets allowed
  • Free parking
  • Suitable for events
  • Balcony
  • Private living room
  • Suitable for children
  • Suitable for infants
  • Iron board
  • Linens
  • Outdoor grill
  • Toaster
  • Dishwasher
  • Microwave
  • Oven
  • Electric kettle
  • Coffee/tea maker
  • Shower
  • Tub
  • Baby crib
  • Stove
  • Refrigerator
  • Towels
  • Dining room
  • Garden or backyard
  • High chair
  • Kitchen utensils
  • Hot water
  • Private entrance
  • Extra pillows and blankets
  • Cooking basics
  • Beach essentials
  • Garage
  • Laundromat
  • Bay
  • Coin laundry
  • Health beauty spa
  • Marina
  • Museums
  • Theme parks
  • Water parks
  • Winery tours
  • Zoo
  • Toilet
  • Car not necessary
  • Childrens dinnerware
  • Pack n play travel crib
  • Dining area
  • Ice maker
  • Antiquing
  • Bird watching
  • Boating
  • Eco tourism
  • Gambling
  • Horseback riding
  • Outlet shopping
  • Paddle boating
  • Shopping
  • Water sports
  • Wildlife viewing
  • Beach
  • Beach view
  • Near ocean
  • Ocean front
  • Ocean view
  • Water view
  • Waterfront
  • Bicycle
  • Golf
  • Kayak canoe
  • Tennis
  • Water sports gear
  • Luggage dropoff allowed
  • Long term stays allowed
  • Deadbolt lock
  • Breakfast possible
  • Cleaning optional
  • Chauffeur
  • Massage
  • Private chef
  • Basketball court
  • Cycling
  • Deepsea fishing
  • Fishing
  • Fishing bay
  • Fishing fly
  • Fishing freshwater
  • Fishing surf
  • Golf
  • Hiking
  • Hunting
  • Jet skiing
  • Kayaking
  • Mountain biking
  • Parasailing
  • Pier fishing
  • Sailing
  • Scuba or snorkeling
  • Water Skiing
  • Snorkeling
  • Snorkeling diving
  • Surfing
  • Swimming
  • Tubing water
  • Wind surfing
  • Family
  • Historic
  • Romantic
  • Enhanced Cleaning Practices
  • Contactless Check-In/Out
  • Dishes & utensils for children
  • Meal delivery
  • Free WiFi
  • WiFi speed (500+ Mbps)
  • Smart TV
  • Kitchen island
  • Dining table
  • Outdoor furniture
  • Cleaning products
  • Body soap
  • Conditioner
  • Clothing storage
  • Board games
  • Ceiling fan
  • Baking sheet
  • Barbeque utensils
  • Blender
  • Coffee
  • Freezer
  • Wine glasses
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Other Details

  • Check-In: 04:00 PM
  • Check-Out: 10:00 AM
  • Additional Rules:
    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.
    >91 days before your arrival all funds refundable less $300
    <90 days no refund
    Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. $500 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 and Amenity Waiver for anyone 18 +. The use of the Street Legal Golf Cart requires a signed Golf Cart Agreement, valid driver's license and proof of auto insurance.
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  • This is a lovely property that is large enough for four adults to spend the holidays. It was a little chilly and windy when we were there, but with the bikes + golf cart we were able to all have enough space and time to not go crazy (all of us being introverts). We did cook every night while we were there, which was a little tricky as the kitchen only had one oven-safe dish that actually fit in the oven and only one sautee pan over ~6" diameter. We cooked in a lot of batches -- but it worked! Overall, this was a great, very clean place in a very convenient location. Thank you so much for letting us stay!
    10 January 2, 2023
  • Sky house is in a perfect location at the N end of Anna Maria. You can sit on the screened in porch and enjoy your coffee in the morning while you look over at the ocean which is visible directly across the street. The house is great for a group of 4 friends, we came for a girl's trip and had a wonderful time. The house had everything we needed. Well stocked kitchen, comfortable furniture and beds, nice linens and TVs in every bedroom for those who like to fall asleep to TV or wake up and watch the news. We had everything we needed for a week's stay. The golf cart and beach chairs were good quality. Beach access points are close by. We asked for 4 bicycles and we got them in perfect condition. The property manager Rick was responsive and friendly, he even took the time from his busy schedule to show us some of his other beachfront properties we may consider for a future stay. We made great memories here, and I would definitely return.
    10 April 25, 2023
  • This house was in a wonderful location, very clean and well kept, with lots of fun toys in the garage- paddle boards, kayak, golf cart! Great communication and an awesome stay!
    10 May 10, 2023
  • This property was amazing! Communication with the host was beyond 5 stars. The property was spotless and was the perfect getaway. loved the interior and the comfortable beds!
    10 June 12, 2023