Anna Maria Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Anna Maria vacation rentals

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, (17 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 CA $707
CA $990 total
includes taxes & fees
Apr 10 - Apr 11
Beach Don't Kill My Vibe by Beach Boutique 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, (16 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
The price is CA $584
CA $1,224 total
includes taxes & fees
Apr 11 - Apr 12
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
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, (32 reviews)
"Amazing place and location "
United States
Evelyn C.
The price is CA $723
CA $1,544 total
includes taxes & fees
Apr 13 - Apr 14
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
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 CA $631
CA $1,179 total
includes taxes & fees
Apr 12 - Apr 13
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Beach nearby, sun loungers

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, (23 reviews)
"Mom and I just stayed for one night and had a lovely trip. "
United States
Brittany B.
The price is CA $383
CA $890 total
includes taxes & fees
Apr 15 - Apr 16
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
A heated pool

Gulf View Retreat! Pool, Decks and 2 King Beds!

Gulf View Retreat! Pool, Decks and 2 King Beds!
Anna Maria
9.6 out of 10, Exceptional, (24 reviews)
"Right on the beach"
United States
Hussein M.
The price is CA $671
CA $1,832 total
includes taxes & fees
Apr 23 - Apr 24
Gulf View Retreat! Pool, Decks and 2 King Beds!
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
Property grounds

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (26 reviews)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is CA $618
CA $1,554 total
includes taxes & fees
Mar 27 - Mar 28
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Interior

Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!

Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!
Anna Maria
9.6 out of 10, Exceptional, (30 reviews)
"Perfect location as it was near the beach and some of our favorite shops and restaurants. The house was great for a few people and the kitchen was spacious. The backyard was nice in the evenings and we even could hear live music from Harry’s. One bathroom doesn’t have any counter space which is odd as it was just remolded but we made it work. "
United States
Jennifer G.
Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!
Pool

Kiwi Cottage~Private Heated Pool!~Shopping close!

Kiwi Cottage~Private Heated Pool!~Shopping close!
Anna Maria
The price is CA $823
CA $1,709 total
includes taxes & fees
Mar 28 - Mar 29
Kiwi Cottage~Private Heated Pool!~Shopping close!
TV, DVD player

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Anna Maria
7.8 out of 10, Good, (78 reviews)
"Great location and layout."
United States
Terri R.
The price is CA $597
CA $1,218 total
includes taxes & fees
Mar 28 - Mar 29
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Fridge, microwave, oven, stovetop

Escape to Anna Maria Island!

Escape to Anna Maria Island!
Anna Maria Island
10.0 out of 10, Exceptional, (130 reviews)
"Great place. Great host."
United States
Anastasio
The price is CA $432
CA $900 total
includes taxes & fees
Mar 26 - Mar 27
Escape to Anna Maria Island!
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
9.0 out of 10, Wonderful, (9 reviews)
" The place was great, and the location to the beach was wonderful."
United States
Norman N.
The price is CA $437
CA $1,017 total
includes taxes & fees
Apr 19 - Apr 20
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
Beach nearby

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

Mermaid’s Purse~Private Pool! 40 steps to beach!
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Perfect location and great service. Thanks for allowing us to make life long memories with our kids!"
United States
Magen S.
The price is CA $755
CA $1,776 total
includes taxes & fees
Apr 12 - Apr 13
Mermaid’s Purse~Private Pool! 40 steps to beach!
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)
"Great property!"
United States
Jessica S.
The price is CA $591
CA $1,223 total
includes taxes & fees
Apr 21 - Apr 22
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
On the beach

Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (153 reviews)
"Location was perfect, house was comfortable and well-stocked"
United States
Laura E.
The price is CA $834
CA $1,408 total
includes taxes & fees
Apr 13 - Apr 14
Do you love the beach?
Pool

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

Coast is Clear! Heated pool/spa~Close to shops
Anna Maria
Coast is Clear! Heated pool/spa~Close to shops
Outdoor dining

Private Home 1 Block to Beach with Pool and Hot Tub!

Private Home 1 Block to Beach with Pool and Hot Tub!
Anna Maria
9.8 out of 10, Exceptional, (46 reviews)
"Great location. Perfect for families and quiet at night. Kids loved the pool and the close walk to the beach. 3 close restaurant's within a block. Beds were comfortable! "
United States
Brenna S.
The price is CA $926
CA $1,993 total
includes taxes & fees
Mar 29 - Mar 30
Private Home 1 Block to Beach with Pool and Hot Tub!
Exterior

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, (34 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is CA $549
CA $1,458 total
includes taxes & fees
Apr 14 - Apr 15
Beautiful Guest House Near the Beach with Private Pool!
Interior

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
Anna Maria
9.8 out of 10, Exceptional, (12 reviews)
"Well maintained propert and enjoyed our stay."
United States
Mathew S.
The price is CA $1,647
CA $3,335 total
includes taxes & fees
Apr 22 - Apr 23
Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
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

Love Shack on the Water Most desirable location on AMI

Love Shack on the Water Most desirable location on AMI

10/10 Excellent
"Really enjoyed our stay. The location can’t be beat! Clean. Comfortable beds. Plenty of room. Everything we needed was in the unit. I highly recommend this property."
Vickie P. 7-night trip
Posted 1 day ago
Love Shack on the Water Most desirable location on AMI

Find out more about Anna Maria

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Anna Maria. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley, Dog*(See Note) Friendly!: Visitors give good reviews to this Anna Maria vacation home rental, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the private yard in this rental home to help you unwind. Other favorite homes for rent in Anna Maria are Bayfront Home with Amazing Water Views! Private pool! – Breakaway and Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi & Trolley.

How many vacation rentals are there in Anna Maria?

With 521 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.