Anna Maria Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Anna Maria holiday 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.
The price is HK$3,324
HK$6,973 total
includes taxes & fees
1 Mar - 2 Mar
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.
The price is HK$3,206
HK$6,804 total
includes taxes & fees
17 Feb - 18 Feb
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
The price is HK$3,713
HK$9,814 total
includes taxes & fees
10 Mar - 11 Mar
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.
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
The price is HK$2,414
HK$6,096 total
includes taxes & fees
11 Mar - 12 Mar
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.
The price is HK$3,324
HK$6,964 total
includes taxes & fees
18 Feb - 19 Feb
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.
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.
The price is HK$2,806
HK$5,641 total
includes taxes & fees
12 Mar - 13 Mar
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
2 bedrooms, iron/ironing board, travel cot, 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
The price is HK$3,557
HK$6,668 total
includes taxes & fees
4 Mar - 5 Mar
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.
The price is HK$5,933
HK$10,759 total
includes taxes & fees
21 Feb - 22 Feb
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.
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.
The price is HK$3,818
HK$5,286 total
includes taxes & fees
23 Feb - 24 Feb
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.
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
The price is HK$3,127
HK$8,654 total
includes taxes & fees
20 Feb - 21 Feb
Mermaid’s Purse~Private Pool! 40 steps to beach!
Outdoor pool, a heated 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.
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
The price is HK$5,472
HK$10,795 total
includes taxes & fees
11 Mar - 12 Mar
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
The price is HK$2,736
HK$7,631 total
includes taxes & fees
1 Mar - 2 Mar
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.
The price is HK$2,988
HK$6,771 total
includes taxes & fees
16 Mar - 17 Mar
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
The price is HK$2,345
HK$7,113 total
includes taxes & fees
17 Feb - 18 Feb
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.
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 5 days ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Find out more about Anna Maria

Search for holiday rentals in Anna Maria on Expedia! You can easily find your home rentals, villas, holiday apartments in Anna Maria using one of the methods below:

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Look no further and take a look at our great range of rental properties in Anna Maria!

Frequently asked questions

Can I find a holiday rental in Anna Maria?

Yes, there are holiday rentals close to the most popular sights in Anna Maria, or you can select 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 holiday rentals that Anna Maria has to offer?

Waterfront -Canal, Tampa Bay, Large Heated Pool, Tiki Bar, Minutes to the Beach!: This highly rated holiday home rental in Anna Maria is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Other favourite 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 holiday rentals are there in Anna Maria?

With 453 Expedia holiday rentals, you're guaranteed 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 such as Lido Beach and Tampa Bay.

What are holiday rentals like in Anna Maria?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Anna Maria. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.