4 Dreamy Anna Maria Island Rentals for the Holidays
Booking a vacation rental for the holidays through Island Dreams Realty is one of the best ways to enjoy a stress-free, truly authentic island getaway. We know the area inside and out and can offer personalized recommendations and curated vacation rentals that match your holiday style – whether you’re dreaming of beachfront mornings, cozy family gatherings, or festive sunsets over the Gulf. Stay with us this holiday season and make the most of an unforgettable escape in one of Florida’s most charming coastal towns!
Anna Maria Island Vacation Rentals for the Holiday Season
For those Traveling with their Furry Family Member
Viva La Flamingo | 3 Beds | 2 Baths | 8 Guests
Traveling with the pup in tow? Viva La Flamingo in Bradenton offers an oversized fenced-in backyard where your dog can freely run around and cherish the vacation as much as you do! The humans will love the private heated pool, spacious layout, and outdoor space. The home is just minutes away from the white sand beaches of Anna Maria Island and Bradenton’s bustling downtown area. Explore the outdoors, dog-friendly restaurants, and more during your holiday getaway.
For the Chef in the Family
Seastar | 3 Beds | 2 Baths | 6 Guests
If you prefer to cook your own meals on your Anna Maria Island vacation, Seastar’s kitchen is the perfect place to craft your gourmet homemade dishes. The kitchen comes equipped with stainless steel appliances and there is also a propane BBQ to cook steaks and your catch-of-the-day! Reminisce on the day’s adventures at the dining room table made for 8, or dine on the outdoor patio with a view of the gorgeous pool.
For those Who Prefer a Beachfront Stay
La Casa Costeria #6 | 3 Beds | 2.5 Baths | 6 Guests
Elevate your holiday stay in one of our Anna Maria Island beachfront rentals. La Casa Costeria #6 offers guests Gulf front living where you can take in spectacular sunset views on the private large balcony and be just steps from the beach. A stay at La Casa Costeria means you’ll have access to the condo complex’s heated swimming pool and hot tub.
For a Larger Family/Group Getaway
No Bad Days | 4 Beds | 2 Baths | 8 Guests
If you need a little more space than a condo or villa can give you, consider one of our Anna Maria Island or Bradenton vacation home rentals for your holiday stay. No Bad Days features 4 bedrooms, with two of the rooms are furnished with king sized beds, one with a queen sized bed, and the fourth with a bunk bed. Explore Bradenton and nearby AMI, or take advantage of the home’s amenities such as the private heated pool, hot tub, and boat dock.
Frequently Asked Questions
- What is the weather like on Anna Maria Island during the holidays?
You can expect warm weather in December on Anna Maria Island, typically in the 70s with cooler evenings. - Are restaurants and shops open on Christmas and New Year’s?
Many local businesses will be closed on Christmas and New Year’s, but there are a few that are open or have adjusted hours during the holiday season. It’s best to visit their website for up-to-date information. - Is Anna Maria Island crowded during the holiday season?
Yes – Christmas is a popular time to visit Anna Maria Island, as many look to escape the cold. - What are the best ways to get around the island?
Anna Maria Island offers a free trolley service that takes you through Anna Maria, Holmes Beach, and Bradenton Beach. People also like to rent golf carts and bicycles. - What should I pack for a winter trip to Anna Maria Island?
Pack beachwear, sunscreen, and sandals for daytime fun, along with light layers for cooler nights. Comfortable walking shoes are also great for exploring.
