A marina with boats, a bridge, and high-rise buildings.

Anna Maria Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anna Maria vacation rentals

1. Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B
Anna Maria
9.8 out of 10, Exceptional, (32 reviews)
"I was impressed with how clean this place is. Location was very close to the beach and all restaurants. Host was very responsive. Definitely will come back!!"
United States
Randa B.
Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

2. Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Anna Maria
9.8 out of 10, Exceptional, (40 reviews)
"Amazing stay! location was perfect, the unit was clean and the host was so kind/accommodating!"
United States
Kyle K.
The price is CA $220
CA $650 total
includes taxes & fees
Sep 23 - Sep 24
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

3. Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
Anna Maria
9.6 out of 10, Exceptional, (29 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
The price is CA $230
CA $678 total
includes taxes & fees
Sep 14 - Sep 15
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

4. Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (33 reviews)
"Great place to stay!Nice walk to the beach!"
United States
Rose Y.
The price is CA $225
CA $666 total
includes taxes & fees
Sep 29 - Sep 30
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

5. Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
The price is CA $102
CA $540 total
includes taxes & fees
Sep 21 - Sep 22
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

6. Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Anna Maria
9.4 out of 10, Exceptional, (30 reviews)
"Old Florida charm of cottage. Beautiful location and only steps to the beach. Staff was wonderful and room was clean."
United States
Christina R.
The price is CA $230
CA $678 total
includes taxes & fees
Sep 14 - Sep 15
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

7. Updated bayside condo with heated pool - across the street from the beach

Updated bayside condo with heated pool - across the street from the beach
Anna Maria
The price is CA $121
CA $550 total
includes taxes & fees
Sep 27 - Sep 28
Updated bayside condo with heated pool - across the street from the beach

8. Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria
9.8 out of 10, Exceptional, (56 reviews)
"Great stay. "
United States
courtneyharned
The price is CA $219
CA $627 total
includes taxes & fees
Sep 14 - Sep 15
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

9. Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Anna Maria
9.6 out of 10, Exceptional, (49 reviews)
"Yes! The cottage was nicely decorated and we had everything we needed for our 2 night stay"
United States
J I.
The price is CA $225
CA $657 total
includes taxes & fees
Sep 21 - Sep 22
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

10. Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Anna Maria
9.8 out of 10, Exceptional, (73 reviews)
"This house is in an excellent location halfway between the bay and the gulf, on a street very close to dining, shopping, etc. and yet quiet. Took only four minutes to walk to coffee shop, eight minutes to the beach and restaurants. House was perfect for our family weekend vacation. We all enjoyed the pool. Washer/dryer on site was convenient. Check in was super easy with door code. Property was clean. Everything worked out well, no issues."
United States
Teresa
The price is CA $298
CA $1,188 total
includes taxes & fees
Sep 29 - Sep 30
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

11. Emerald Shores East! Walk to Beach!

Emerald Shores East! Walk to Beach!
Anna Maria
9.0 out of 10, Wonderful, (12 reviews)
"Clean spot and a great stay. Amazing location and 10/10 service / review. "
United States
Christopher B.
The price is CA $224
CA $1,016 total
includes taxes & fees
Oct 5 - Oct 6
Emerald Shores East! Walk to Beach!

12. Dog friendly cottage - One block to the Bay!

Dog friendly cottage - One block to the Bay!
Anna Maria
9.6 out of 10, Exceptional, (15 reviews)
"Great location!"
United States
Jennifer L.
The price is CA $212
CA $788 total
includes taxes & fees
Sep 7 - Sep 8
Dog friendly cottage - One block to the Bay!

13. Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
Anna Maria
9.2 out of 10, Wonderful, (14 reviews)
"Close walk to the beach "
United States
Zev C.
The price is CA $282
CA $801 total
includes taxes & fees
Sep 14 - Sep 15
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

14. Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (160 reviews)
"We really enjoyed this location - steps away from the beach was awesome. Also walking distance from some of our favorite spots (Waterfront, Donut Experiment, North Shore, Poppo’s, Two Scoops). We will be booking this spot on our next trip to Anna Maria."
United States
Zachary Z.
Do you love the beach?

15. Beachside Duplex w/ Pool and Private Suite

Beachside Duplex w/ Pool and Private Suite
Anna Maria
9.6 out of 10, Exceptional, (5 reviews)
"Amazing relaxing time, perfect accommodations for our budget"
United States
Sandi L.
The price is CA $266
CA $1,083 total
includes taxes & fees
Sep 7 - Sep 8
Beachside Duplex w/ Pool and Private Suite

16. Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
The price is CA $325
CA $1,149 total
includes taxes & fees
Sep 11 - Sep 12
Beautiful Guest House Near the Beach with Private Pool!

17. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is CA $412
CA $902 total
includes taxes & fees
Sep 7 - Sep 8
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

18. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is CA $276
CA $1,174 total
includes taxes & fees
Sep 9 - Sep 10
Adorable Cottage with Covered Balconies and Private Pool

19. The Hideaway - Less than a block from beach!

The Hideaway - Less than a block from beach!
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great. So close to the beach a 3 min walk. We loved everything about it."
United States
JASON G.
The price is CA $356
CA $1,257 total
includes taxes & fees
Sep 29 - Sep 30
The Hideaway - Less than a block from beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Anna Maria Hotel Reviews

Find out more about Anna Maria

Everything you need to know about Anna Maria vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna Maria vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria vacation rentals we have selected for you start as low as CA $1,086 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anna Maria rentals

At Expedia, we put the best Anna Maria vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Anna Maria rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Anna Maria?

Yes, we give you a choice of vacation rentals close to top points of interest in Anna Maria, or you can go with a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Anna Maria. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best vacation rentals that Anna Maria has to offer?

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!: Visitors give good reviews to this Anna Maria vacation home rental, which is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Anna Maria are Coral Cove: Walk to the Beach! Heated pool! Prime North End! and ANNA MARIA GEM- adorable 3BR/2BA NEWLY REDONE HOUSE -JUST STEPS FROM THE BEACH.

How many vacation rentals are there in Anna Maria?

With 604 Expedia vacation rentals, you're sure to find just the right place for your Anna Maria stay.

What can I see and do in Anna Maria?

Cultural attractions include Anna Maria Island Museum and Historical Park and Island Players, whereas Anna Maria Beach and Bean Point Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places like Lido Beach and Tampa Bay.

What are vacation rentals like in Anna Maria?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Anna Maria. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips.