Anna Maria Island Cottage Rentals & Holiday Homes
Find the best cottages in Anna Maria Island - We found 237 exact matches
About Anna Maria Island Luxury Rental on Orlando Vacation Rentals
Searching for cottages to rent near Anna Maria Island? Orlando Vacation Rentals features more than 237 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Anna Maria Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Orlando Vacation Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Anna Maria Island.
Are you planning to travel to the lakeside, beach, or mountain area? Orlando Vacation Rentals’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Orlando Vacation Rentals boasts of 237 holiday cottages and places to stay in Anna Maria Island. The site provides unique Airbnb, VRBO, Orlando Vacation Rentals-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Anna Maria Island Cottage Rentals
What are the top rated Cottage Rentals in Anna Maria Island?
There are a lot of options in Anna Maria Island. If you plan on staying in the Anna Maria Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Anna Maria Island:
- Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
- Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
- Coastal Charm Meets Cottage Chic! Sparkling Pool/Spa *4 Doors To The Beach*
- Turtle Cottage - Anna Maria Island
- Beach across the road, pool a few steps out the door of this charming cottage.
- Blue Heron Cottage - Anna Maria Island
- END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!
- Newly Renovated – Fresh, Modern Cottage Private Pool Just Steps from the Gulf!
- Relaxed Quiet Private Get Away
- Welcome to Beach Basket – Your Seaside Retreat!"
How much does it cost to rent a cottage in Anna Maria Island?
The average cost for a cottage rental in Anna Maria Island is $494 per night. Orlando Vacationrentals has a wide list of great cottages near Anna Maria Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Anna Maria Island that allow pets?
Yes, here are the top cottage rentals in Anna Maria Island that allow you to bring your pet:
- Charming cottage in quiet area, close to beach & bay.
- Coconut Cottage #4 by AMI Locals
- Tropical Landscaped Beach Cottage with Heated Jetted Pool
- GREAT COTTAGE w/Heated Pool, Dog- See Note - Allowed, FREE WiFi/Trolley, Steps to Beach, Dining.
See all pet-friendly vacation rentals in Anna Maria Island on Orlando Vacationrentals
Do you have any rental cottages in Anna Maria Island that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Anna Maria Island to find one that works for you.
Are there quality cottages in Anna Maria Island that have indoor swimming pools?
As of 2026, the data from Orlando Vacationrentals shows that there are Over 237 private swimming pools or cottages with indoor pools in the Anna Maria Island area along with other great amenities.
