Anna Maria Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Anna Maria vacation rentals

Beach nearby, sun loungers

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
9.8 out of 10, Exceptional, (14 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
$801 nightly
The price is $892
Feb 16 - Feb 17
Total with taxes and fees
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Property grounds

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
8.8 out of 10, Excellent, (8 reviews)
" The place was great, and the location to the beach was wonderful."
United States
Norman N.
$782 nightly
The price is $870
Feb 16 - Feb 17
Total with taxes and fees
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
Property grounds

The Hideaway - Less than a block from beach!

The Hideaway - Less than a block from beach!
Anna Maria
$1,126 nightly
The price is $1,256
Mar 10 - Mar 11
Total with taxes and fees
The Hideaway - Less than a block from beach!
Terrace/patio

Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria! - Hip Nautic

Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria! - Hip Nautic
Anna Maria
9.8 out of 10, Exceptional, (15 reviews)
"We had a great time and the accommodations were great. "
United States
Sara B.
$1,345 nightly
The price is $1,498
Feb 15 - Feb 16
Total with taxes and fees
Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria! - Hip Nautic
Beach nearby

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.8 out of 10, Exceptional, (39 reviews)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
$699 nightly
The price is $780
Mar 11 - Mar 12
Total with taxes and fees
Beautiful Bungalow with Pool and Bay Views!
Beach nearby, sun loungers

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Anna Maria
10.0 out of 10, Exceptional, (25 reviews)
"The cottage was clean, well appointed with great proximity to the beach. Would definitely stay here again. "
United States
Melissa E.
$800 nightly
The price is $891
Feb 18 - Feb 19
Total with taxes and fees
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Outdoor pool, a heated pool

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT
Anna Maria
9.6 out of 10, Exceptional, (4 reviews)
"The house is beautiful!! Plenty of room for a family, and plenty to do!The owner was readily available through messages and the phone if we had any questions. It was an easy process, and an excellent experience!!!I highly recommend this house if you just feel like hanging out, or exploring Anna Maria, it’s a beautiful location!!And don’t forget to go down the slide!! "
United States
Patricia H.
$1,908 nightly
The price is $2,125
Mar 1 - Mar 2
Total with taxes and fees
Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT
Smart TV, Netflix, DVD player, streaming services

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, (123 reviews)
"Great place and great location........"
United States
chris w.
$647 nightly
The price is $722
Mar 12 - Mar 13
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
2 bedrooms, iron/ironing board, travel crib, free WiFi

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Anna Maria
9.8 out of 10, Exceptional, (177 reviews)
"Perfect. "
United States
Mary Suzanne
$766 nightly
The price is $853
Mar 4 - Mar 5
Total with taxes and fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Beach nearby, sun loungers, beach towels

Charming cottage with heated pool, tropical landscaping in prime location.

Charming cottage with heated pool, tropical landscaping in prime location.
Anna Maria
10.0 out of 10, Exceptional, (60 reviews)
"We had a wonderful stay at this property. Perfect condition and location. The air conditioning did stop working on Friday evening, but the host was very responsive and had it repaired by Saturday morning. I would 100% book this property again. "
United States
Shannon g.
$1,233 nightly
The price is $1,376
Feb 21 - Feb 22
Total with taxes and fees
Charming cottage with heated pool, tropical landscaping in prime location.
Beach nearby, sun loungers

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
Anna Maria
10.0 out of 10, Exceptional, (30 reviews)
"Amazing place and location "
United States
Evelyn C.
$1,011 nightly
The price is $1,126
Feb 16 - Feb 17
Total with taxes and fees
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
Property grounds

Beach Don't Kill My Vibe by Beach Boutique Rentals

Beach Don't Kill My Vibe by Beach Boutique Rentals
Anna Maria
10.0 out of 10, Exceptional, (16 reviews)
"We really enjoyed our brief stay here. Very clean. Great location. Very helpful staff/owner. Great location."
United States
Drew N.
$606 nightly
The price is $676
Feb 23 - Feb 24
Total with taxes and fees
Beach Don't Kill My Vibe by Beach Boutique Rentals
Beach nearby, sun loungers

Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!

Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Anna Maria
9.6 out of 10, Exceptional, (36 reviews)
"The cottage was cute and rooms/bathrooms were clean. It's on a nice quiet side street with a very short walk to the beach. Would definitely stay here again and would recommend to others."
United States
sherri g.
$977 nightly
The price is $1,088
Feb 16 - Feb 17
Total with taxes and fees
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Beach nearby

Mermaid’s Purse~Private Pool! 40 steps to beach!

Mermaid’s Purse~Private Pool! 40 steps to beach!
Anna Maria
$994 nightly
The price is $1,107
Feb 20 - Feb 21
Total with taxes and fees
Mermaid’s Purse~Private Pool! 40 steps to beach!
Pool

Feelin' Salty-Pool Modern Beach House w/Pool/Spa

Feelin' Salty-Pool Modern Beach House w/Pool/Spa
Anna Maria
10.0 out of 10, Exceptional, (5 reviews)
"Great pool and short walk to bay and beach!"
United States
Eric S.
$643 nightly
The price is $719
Feb 17 - Feb 18
Total with taxes and fees
Feelin' Salty-Pool Modern Beach House w/Pool/Spa
Pool

Kiwi Cottage~Private Heated Pool!~Shopping close!

Kiwi Cottage~Private Heated Pool!~Shopping close!
Anna Maria
$999 nightly
The price is $1,113
Feb 14 - Feb 15
Total with taxes and fees
Kiwi Cottage~Private Heated Pool!~Shopping close!
Pool

Coast is Clear! Heated pool/spa~Close to shops

Coast is Clear! Heated pool/spa~Close to shops
Anna Maria
$877 nightly
The price is $976
Mar 1 - Mar 2
Total with taxes and fees
Coast is Clear! Heated pool/spa~Close to shops
Terrace/patio

Dog friendly cottage - One block to the Bay!

Dog friendly cottage - One block to the Bay!
Anna Maria
9.6 out of 10, Exceptional, (11 reviews)
"Great stay. "
United States
Mandy R.
$796 nightly
The price is $889
Mar 16 - Mar 17
Total with taxes and fees
Dog friendly cottage - One block to the Bay!
Terrace/patio

Coconut Cottage~Private Heated Pool~Block to shops

Coconut Cottage~Private Heated Pool~Block to shops
Anna Maria
$937 nightly
The price is $1,044
Feb 16 - Feb 17
Total with taxes and fees
Coconut Cottage~Private Heated Pool~Block to shops
Beach nearby, sun loungers

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, (25 reviews)
"Easy walk to the beach and restaurants. Allowed us to check in early since the place was available. "
United States
Nancy E.
$610 nightly
The price is $680
Mar 12 - Mar 13
Total with taxes and fees
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
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.
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Top Anna Maria Hotel Reviews

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10/10 Excellent
"We had an absolutely wonderful experience here! From the moment we arrived, it was clear that the hosts truly care about their guests. They were incredibly responsive, welcoming, and thoughtful providing clear instructions, local recommendations, and making sure we had everything we needed for a smooth and relaxing stay.The highlight of the property was hands-down the breathtaking sunset views. Each evening felt like a private show, with gorgeous colors lighting up the sky. Whether enjoying dinner on the patio or simply relaxing with a drink, the views made every moment special.The amenities were top-notch and exactly as described clean, and well-maintained. The home was fully stocked with everything we needed, from kitchen essentials to comfortable linens and cozy seating areas. It truly felt like a home away from home.We would absolutely stay here again and highly recommend this property to anyone looking for a peaceful getaway with incredible views and attentive hosts. Thank you for such a memorable stay!"
Lindsey P. 4-night trip
Posted 2 days ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Price trends for vacation rentals in Anna Maria

Less expensive
More expensive
This month
Next month
January
February
$1,007
$886
Month
Price
January
$561
February
$1,007
March
$886
April
$672
May
$710
June
$772
July
$756
August
$619
September
$574
October
$598
November
$597
December
$597
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Anna Maria. Select dates and complete search for nightly totals inclusive of taxes and fees.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Anna Maria in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $332 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Waterfront -Canal, Tampa Bay, Large Heated Pool, Tiki Bar, Minutes to the Beach!: Visitors give good reviews to this Anna Maria vacation home rental, which is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Other favorite homes for rent in Anna Maria are Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit and Bayfront Escape with Stunning Water Views and Steps to Bean Point.

How many vacation rentals are there in Anna Maria?

With 453 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.