When you’re in need of a break, you’ll find everything you need in the year-round sun and warmth of Florida. The decision to head to the Sunshine State may be a no-brainer but planning all the details – from where to go and the fun you’ll have to where to stay seem like a list that never ends. Cross off two of those daunting tasks by choosing Anna Maria Island in the keys, and a vacation rental with Anchor Down. Bay Dreamin’ is a 4-bedroom, 3.5-bathroom Anna Maria vacation home rental with room for up to 8 guests to enjoy the island paradise that is Anna Maria Island.

Book Bay Dreamin’ Here!


  • Central A/C
  • Master Bedroom King + Sitting Area + Full Bath
  • Private Pool & Spa
  • In-Unit Laundry
  • Putting Green

Island Rest & Relaxation

Guests looking for a fun and exciting stay on Anna Maria Island will find everything they’re looking for in a “home base” at Bay Dreamin’. Stylish furnishings and finishes with beachy touches can be found throughout the home, in bedrooms as well as living spaces for plenty of comfort.

Exterior Features

Arrive at the home and take in the beautiful two-story home surrounded by island foliage. The neutral-colored siding covers the home and is trimmed in white. A balcony on the second floor overlooks the neighborhood from a family room/den area. Once you’ve settled, step into the outdoor paradise. Take a dip in the in-ground pool or relax tired muscles after a day of adventure in the spillover spa. Enjoy the island weather under the nearby covered patio featuring outdoor living seating, a wet bar, and wall-mounted flat screen TV. The deck surrounding the pool spreads out into a covered patio with stainless steel BBQ grill and outdoor dining seating. If you want to practice your short game before heading to one of the area’s golf courses, there’s a multi-hole putting green around the corner from the pool area. Rinse off from a day at the beach with a nearby outdoor shower and use the pool bathroom in the garage. Your day at the beach is just steps away! The home is located right across the road from Bayfront Park and Tampa Bay. You can see the bay as well as the Sunshine Skyway Bridge just by stepping outside! There are games like cornhole, plus water toys to keep you busy in the pool and at the beach.

Interior Amenities

Step inside the home to a cozy foyer with beautiful beach décor. You can choose to continue up the stairs or turn into the spacious and airy great room. Look up and notice the beams on the ceiling that create a tray ceiling look. Relax in the living space that features a large wraparound couch facing a wall of windows letting in plenty of natural light. Watch a favorite movie or TV show on the 65” Smart TV. When you’re craving a meal in, turn to the fully equipped kitchen. A myriad of cupboards and drawers are packed with all the utensils and cookware you need to prepare and serve a mouth-watering meal. Spacious counters, including a kitchen island with bar seating for five, join stainless steel appliances to make mealtime a breeze.  Enjoy the meal at the nearby dining table. It’s easy to have a meal al fresco, too, with a glass door leading onto the dining patio from the kitchen. For your convenience, there is a half bath off the living area. Upstairs you’ll find a den/family room with comfortable couch and chairs surrounding a wall-mounted flat screen TV. Upstairs there is a full bath for all the upstairs queen bedrooms to use and another bathroom off the bunk room. There is also a round wood table where you can enjoy tabletop games or a snack during the show. Take in the view of the neighborhood when you step out onto the balcony facing the street.

Relax after a long day of Anna Maria Island fun. Spoil yourself in the master suite, featuring a king size bed, a sitting area with natural light spilling in, a wall-mounted flat screen TV, vaulted ceiling, and en suite bath. The bathroom boasts a separate soaking tub, walk-in shower with multiple shower heads, and double-sink vanity. The second and third bedrooms each boast a queen bed with night tables, dresser, and wall-mounted flat screen TVs. The final bedroom is perfect for kids! They’ll love the twin-over-full bunks and stay entertained for hours with the wall-mounted flat screen TV. There are two more bathrooms, each with a shower and single-sink vanity. There’s space for everyone to enjoy an Anna Maria Island vacation!

Sleeping Accommodations, Sleeps 8

2nd Level | Master Suite – King + Sitting Area + Full Bath

2nd Level | 2nd Bedroom – Queen

2nd Level | 3rd Bedroom – Queen

2nd Level | 4th Bedroom – Twin-Over-Full Bunks x1


  • Driveway

Things to Know:

  • NO Pets
  • NO Smoking
  • Self-Check In/Check Out
  • Additional Fee for Pool Heating
  • In-unit laundry
  • Wi-Fi

Contact Us

No matter when or how long you plan your getaway to Anna Maria Island, Bay Dreamin’ will give you all the excitement, fun, and relaxation you’re looking for.

Contact us today to book a memorable island stay that will have you coming back for years to come!


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Beds | Bed | Baths | Bath | Guests