Anna Maria Vacation Rentals from ￥55,439: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Anna Maria

"Well maintained propert and enjoyed our stay."

￥212,255 total

includes taxes & fees

Sep 1 - Sep 2

Beach nearby, sun loungers, beach towels

"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"

"Our family of 6enjoyed our stay!"

"The location is just a block from the beach and lots of unique restaurants. The pool area is great!"

￥110,951 total

includes taxes & fees

Aug 15 - Aug 16

"The location and amenities are amazing. Would definitely stay here again."

"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"

"Exceptional property! We truly had the most amazing stay. The property is so beautiful and clean. It has a ton of charm, and the view off the entire back of the home of the emerald green bay is unmatched!Between waking up to amazing sunrises, hearing the sound of the water, while enjoying the bay breeze and watching all of the dolphins swim by, it was one of the most serene and tranquil experiences. The pool and spa are brand new and we loved having options to swim in the pool, paddle board...

"This place is wonderful!!! Just a few steps from the beach, the location is excellent! The house was extremely clean and had everything we needed! Everything was perfect and we even had an incredible barbecue. We had a great time!!! Thank you for welcoming us so well. We will definitely be back."

￥198,479 total

includes taxes & fees

Sep 2 - Sep 3

"Great location and amenities. House is deceivingly more spacious than one would expects from the street. Had a great stay! "

"Dolphins everyday. Great spot. Can’t really think of any negatives. Really a nice place."

"Great place "

"The Bungalow was spotless, I had a fantastic stay, thank you !!!"

"Great location. Private beach with great sun rise view. Close to local shops and restaurants "

￥138,490 total

includes taxes & fees

Aug 14 - Aug 15

"Our stay was fantastic. Easy walking access to the beach, trolley and restaurants. "

"Great location! Had a wonderful stay. Kids loved the pool and hot tub. Great walking distance to shops/food. "

"Easy to rent. Great location to the beach, shopping and food."

On the beach, sun loungers, beach towels

"Beautiful Home, Best Location on beach & Perfect family escape"

"We loved the house and the location! Definitely would book this house again."

"Great property and location! Nicole was amazing to work with in planning our vacation and throughout our stay!"

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Anna Maria Hotel Reviews

Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...

10/10 Excellent

"The location of this property combined with its affordability make it a no brainer. The property itself is basic and cute but it is one house from the beach and withing easy walking distance to the Pine Ave shopping and restaurants. It is perfect for the family that is looking for a place to rest, eat, and clean up between beach time and island time. We would definitely stay there again."

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

10/10 Excellent

"We went to Ana Maria Island for a quick beach getaway before school started. August in Florida is extremely hot and the ocean water is very warm. The cottage and all of its amenities offered a reprieve from the Florida Sun. The pool was the perfect temperature to cool off and enjoy outside in the summer heat. The cottage itself had every amenity that you would possibly need during your stay. The location was perfect with beach access very close by, making it easy to get to the beach for the beautiful sunsets. The golf cart was an added bonus and made it easy to get everywhere on the island. We would definitely recommend staying at this cottage and look forward to returning ourselves!"

LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

10/10 Excellent

"My family loved everything about this house! It’s much bigger inside than you would think. Very spacious and clean. I accidentally left my work cell phone there when I checked out so I reached out to the owner. He went above and beyond to help get it shipped back to me. I’ll definitely stay here again!"

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

10/10 Excellent

"Cute beach home close to Bean Pointe! This was our second time staying at this property. This home was perfect before, but has only gotten better with recent renovations after the hurricane in '24. The property is exceptionally clean and functional. You will love the pool and one of our favorite spots was the screened in lanai! The owners are incredibly responsive and they have a great team that manages their property!"

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

10/10 Excellent

"My family and I had a great stay! Plenty of room for the 9 of us. Within walking distance of the beaches, shops and restaurants. The owner was very responsive and made sure we had everything we needed!’"

AUGUST SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

10/10 Excellent

"Stayed 4 nights and overall it was fantastic! Roomy, a great patio area and the backyard is literally the beach. Private parking for 4 cars was a great benefit. And for us dog lovers, being able our precious pooch was a huge plus! Highly recommend for your next beach trip…you won’t be disappointed. "

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:

View our selection of featured holiday rentals in Anna Maria
Use the map to find apartments and other holiday homes in the Anna Maria neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Anna Maria while they last

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

Explore a world of travel with Expedia

All accommodation types in Anna Maria

Resorts in Anna Maria

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?

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!: Visitors give good reviews to this Anna Maria vacation home rental, which offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Anna Maria are Adorable Beach cottage just steps Bean Point beach! and Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!.

How many vacation rentals are there in Anna Maria?

With 783 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Anna Maria Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in Anna Maria

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

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

Adorable Beach cottage just steps Bean Point beach!

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

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Beachfront Home | Pool + Spa | Games | Ocean Views

Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

Near Bean Point!! Short stays available! Heated Pool

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

AUGUST SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Escape to Anna Maria Island!

Private Home on North End AMI. Private Heated Pool

Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Beachfront - New Listing!

Top Anna Maria Hotel Reviews

Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...

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

LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

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

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

AUGUST SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Escape to Anna Maria Island!

Find out more about Anna Maria

Explore a world of travel with Expedia

Frequently asked questions