13 Best VRBO Anna Maria Island Rentals You’ll Love: Book ASAP!
This list contains some of the best VRBO Anna Maria Island rentals that are just what you’re looking for! Here you will find beautiful vacation rentals of all types: beachfront, pet-friendly, rentals with pools, and rentals for large groups. Let’s get started!
This post may contain affiliate links. We may earn compensation when you click on the links at no additional cost to you. This compensation is used to support our website so we can continue to bring you great content. Thank you!
VRBO Anna Maria Island
Anna Maria Island is located on the west side of Florida, just south of Tampa and west of Bradenton. The Island is divided into three different areas: Anna Maria City/Bean Point (the north end), Holmes Beach (the middle), and Bradenton Beach (the southern end). Each area offers something different, so if you’re trying to decide which one is the best fit for your family, check out our Anna Maria Island Guide For Families.
Anna Maria Island: Anna Maria City/Bean Point
Beachfront
- Charming Sea Garden Cottage is a beautiful Anna Maria Island Beachfront rentals located on the north end of the island
- 2 beds, 1.5 baths
- Sleeps 5
- Large fully-equipped kitchen
- On-site laundry
- Screened patio
- 1.23 acre garden oasis located on the Gulf of Mexico
- Semi-private outdoor shower
- Private walkway to the beach
Pet-Friendly
- The Seashell is a VRBO Anna Maria Island pet-friendly condo that is set up like a single family home
- 3 beds, 2 baths
- Sleeps 6
- Open floor plan
- Fully-equipped kitchen with breakfast area
- Private pool with outdoor furniture and grill
- On-site laundry
- One minute walk to the beach
Large Group
- Paradise Point is located across the street from Bean Point Beach and is a great Anna Maria Island rental for large families
- 5 beds, 4 baths
- Sleeps 12
- Private pool with outdoor entertaining area
- Large fully-equipped kitchen
- On-site laundry
Anna Maria Island Rentals With Pool
- Blue Heron Beach House is located on a deep water canal with access to Tampa Bay
- 3 beds, 3 baths
- Sleeps 6
- Large heated pool
- Open floor plan with large fully-equipped kitchen
- Recently renovated
Holmes Beach
Beachfront
- The Tiki is an Anna Maria Island beachfront rental located on the shores of the Gulf of Mexico
- 3 beds, 2 baths
- Sleeps 6
- Recently renovated
- Large, open deck with views of the beach
- On-site laundry
Pet-Friendly
- Honey Beach House is a quaint bungalow just steps from the beach
- 3 beds, 3 1/2 baths
- Sleeps 6
- Fully-equipped kitchen
- On-site laundry
Condo
- This Anna Maria Island condo rentals, AMI Dreaming, is located on Manatee Beach
- 2 beds, 2 baths
- Sleeps 6
- Open floor plan with fully-equipped kitchen
- Washer and Dryer
- Large heated pool
Large Group
- Beach Breeze is a short 1-2 minute walk to the beach and a great Anna Maria Island rental for large families
- 6 beds, 4 1/2 baths
- Sleeps 12
- Roof top deck
- Private heated pool with outdoor kitchen and entertaining area
- Dog-friendly for additional fee
Anna Maria Island Rentals With Pool
- Island Time is located only 3 blocks from the beach
- 3 beds, 2 baths
- Sleeps 6
- Private heated pool
- Large fully-equipped kitchen
- On-site laundry
Bradenton Beach
Beachfront
- Light & Airy Townhouse with both beach access and bay access
- 3 beds, 2 1/2 baths
- Sleeps 6
- Heated pool located right out front of the townhouse
- Open floor plan
- Fully-equipped kitchen
- On-site laundry
- Multiple decks
- This Anna Maria Island beachfront rental is minutes away from restaurants, shops, and historic Bridge Street
Pet-Friendly
- Great Bradenton Beach home with views of Sarasota Bay
- 2 beds, 2 baths
- Sleeps 6
- Open floor plan
- Heated pool and spa
- One block to the beach
Large Group
- Casa Linda is located along the Anna Maria Sound on the east side of the island
- 4 beds, 3 baths
- Sleeps 10
- Large fully-equipped kitchen
- Large pool with outdoor seating
- On-site laundry
Anna Maria Island Rentals With Pool
- Adorable “Old Florida” cottage just minutes from everything in Bradenton Beach
- 3 beds, 2 baths
- Sleeps 8
- A short walk to the beach and Anna Maria Sound
- Fully-equipped kitchen
- Large pool (with optional heating)
- Also pet-friendly
Check out some of our Anna Maria Island Adventures:
28 Comments
Elle Burne
Holmes Beach looks so gorgeous! The rentals all look like such lovely places to stay too – I’ve never been to Florida, bookmarking this for when I get there!
Trisha
Holmes Beach is one of our favorite places to stay on Anna Maria Island. I hope you get the chance to visit Florida soon!
Sharyn
What beautiful places to stay – I could see myself staying there a while in one of the beach houses.
Trisha
I have a feeling if I booked a beachfront vacation rental, I would never leave! Anna Maria Island is so beautiful!
Francesca
Amazing! That beach front house is to dream for! Very good options, thank you for sharing!
Trisha
You’re welcome! There are so many beautiful beachfront vacation rentals options on Anna Maria Island.
Karen
I would love to book all 13 of these VRBOs on Anna Marie Island. They are so charming and beautiful.
Trisha
When you’ve reached your snowfall limits in Minnesota ;), you should book a trip to Anna Maria Island! You and your husband would love it!
Shelbs Lamb
Anna Maria Island looks gorgeous! Love that you included places that have pools too – we love a good night swim!
Trisha
Us too! Since we usually visit Anna Maria Island in the winter months, a VRBO with a heated pool is a must for our family! My kids will be in the pool the entire time.
Jay Hall
This looks so relaxing. I too might never want to leave. Looks like a great place to enjoy with friends. 🍹
Trisha
The great thing about Anna Maria Island is that it appeals to visitors of all ages. There is something for everyone to take part in and there is a VRBO that will check all your boxes.
Chantelle
They are all fabulous looking! I really like Holmes Beach I think!
Trisha
Holmes Beach has a great mix of things to do for the entire family. It’s a great location on the island too.
Lisa Manderino
These are great options for Airbnb on Anna Maria Island. I really want to go, it looks gorgeous!
Trisha
I hope you get the chance to visit Anna Maria Island someday. It’s hands down one of our favorite places to go as a family.
Cindy Moore
What beautiful properties! I’d stay in any of them. Just a suggestion…I have no idea where Anna Maria Island is. You might include the state/location!
Trisha
Thank you for the feedback, Cindy! Anna Maria Island is located on the Gulf side of Florida, just south of Tampa and west of Bradenton.
When I’m writing a post and I get so excited sharing about that place, I sometimes forget that not everyone might know where it is. 😉 I hope you get the chance to visit Anna Maria Island soon.
Jordin
Just beautiful!!! I would love to stay at any of these especially during these cold winter months. I would prefer the beach front or pet friendly so I could bring my pups!
Trisha
Every winter you can usually find us in a VRBO on Anna Maria Island! It’s a beautiful place to just relax! Sometimes we bring our dog along too.
Marianne
I would love to stay at a place that has its own private pool! So many of these rentals are absolutely gorgeous!
Trisha
VRBO’s with pools are a huge hit with my kids! There are a great way to cool down from the heat and the kids can play in it all day!
Barbara
I appreciate your recommendations as we are trying to make plans!
Trisha
That’s awesome! I hope you are able to find the perfect VRBO on Anna Maria Island. Have a wonderful trip!
Julie
These are some pretty spectacular VRBO rentals on Anna Maria Island! I would have a hard time choosing.
Trisha
I think we just plan a trip to AMI and try our each VRBO. 😉 We can just tell out husbands it’s research!
Maria Khan
I like Anna Maria Island. This looks so beautiful.
Trisha
Anna Maria Island is such a beautiful area! Very family-friendly with tons to do!