Holiday Rentals Anna Maria from £637: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Anna Maria has to offer?

Charming Bungalow with Fabulous Location and Private Pool! : This highly rated holiday home rental in Anna Maria is located near the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games. Other favourite homes for rent in Anna Maria are Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear and Beachfront - New Listing! .

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Top Holiday Rentals in Anna Maria

"Beautiful home and great location. Close to the beach, food and ice cream. Will definitely stay here again. Host was really responsive. "

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

includes taxes & fees

27 Jul - 28 Jul

"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!"

"By far my favorite place I have stayed. Everything we needed was provided. Honestly could not have asked for a better hose and amenities. Restaurants were a short drive away and the beach was beautiful. Looking forward to booking again next year. "

"Beautiful property with all the little details thought of to make our stay cozy! Would definitely come back "

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

"Plenty of room for a family with a 3 minute walk to the beach! Quiet location considering how busy the island is. "

"While this property has incredible potential, it was clearly not ready to be rented at the time of our stay. The host did not even own the property at the time we booked on VRBO. Photos on the listing were renderings and photo-shopped. Falsely claimed sleeping for 16 people. Numerous safety hazards and the majority of the listed amenities were not provided. "

"Nice property,, the location is walking distance to restaurants, and across the street from beach access. We would definitely stay at this property again!"

"Excellent place for relaxing beach vacation"

"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."

"Enjoyed"

"We really enjoyed our stay!"

"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."

"I would definitely recommend or stay here again"

"Easy and close beach access. Location nearby all amenities and necessities. Did not see that the a/c units were window units, the bedroom unit is AMAZING, however the main room unit was mediocre. The Wee Cottage is adorable!!!"

"Great proximity to restaurants, bars, and the beach!"

Beach nearby, sun-loungers, beach towels

"Everything about this house was perfect for us close to the beach, quiet end of the island and the pool was perfect, will be returning again "

"Great Place We will be back Thank You! Dave and Kathy"

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

Sign in

Sign up, it's free

Find out more about Anna Maria

Everything you need to know about Anna Maria holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria holiday rentals we have selected for you start as low as £637 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 holiday 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 holiday.

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.

Recent reviews of Anna Maria properties

Charming cottage in quiet area, close to beach & bay.

5/5 Excellent

Great stay!

"We had a lovely stay at this adorable beach cottage. It is well equipped with everything you’d need for the perfect beach day. Great location being walking distance to the beach, shops, and restaurants. The home was clean and comfy. Would stay again! "

A verified traveller stayed at Charming cottage in quiet area, close to beach & bay.

Posted 3 days ago

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

5/5 Excellent

Best family vaction

"The house was perfect for a family vacation with older children/grandchildren. The grandparents and parents had their space and the children/grandchildren had their space. With a beautiful pool area to hang out together and the beautiful beach across the street!"

A verified traveller stayed at Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Posted 6 days ago

Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

5/5 Excellent

"By far my favorite place I have stayed. Everything we needed was provided. Honestly could not have asked for a better hose and amenities. Restaurants were a short drive away and the beach was beautiful. Looking forward to booking again next year. "

A verified traveller stayed at Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

Posted 2 weeks ago

Charming Bungalow with Fabulous Location and Private Pool!

5/5 Excellent

"The house was renovated very nicely. It has a warm farmhouse beachy vibe with all the amenities. My favorite of course was the backyard with a great pool. We all were very comfortable and enjoyed ourselves greatly. I could not have picked a better place than this cute bungalow with great hosts. Thank you!"

A verified traveller stayed at Charming Bungalow with Fabulous Location and Private Pool!

Posted 3 weeks ago

Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

5/5 Excellent

Great Home Very Close to the Beach!

"It was the perfect size for our family of four! It was practically on the beach for easy access to and from. We spent a lot of time in the pool which was the perfect temp and had some shade throughout the day to get a break from the sun! Easy instructions to access the property and to turn on the hot tub (which got super hot!!). The golf cart inclusion was a perk as the home is located right off of Pine St. We were able to get morning donuts and coffee and shop during the day as well as make stops for ice cream in the evening. Within walking distance to many restaurants. It was in a prime location! We very much enjoyed our stay!"

A verified traveller stayed at Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

Posted 3 weeks ago

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

4/5 Good

Fantastic location for couples or family of 4

"Outstanding location steps away from the beach. Wonderfully renovated house that is clean, tidy, and cozy. Fresh furniture, beds, linens, and fixtures. Pool is delightful with privacy fencing and temperature control. I don't think anyone could do better on Anna Maria Island if you're a couple or family of 4.This would have been a 10/10 but there were some basic things missing for a beach house. The misses are probably because it's a totally refurbished property. They can easily be fixed. There was only 1 trashcan in the house and it was in the master bath. The wifi name and password provided weren't valid. Management company never responded to text about this. There were no pool floats, not even a noodle. No umbrella for poolside table. For the beach, no cooler, no tote bag, no insulated tumblers with lids, no umbrella, no chairs, etc. Having rented many beach places over the years and flying to destinations, those are minimum expectations. Fortunately for the next guests, I left a beach umbrella & spike, chairs, and noodles to help things along the way. Hopefully the property management can fill in the other gaps. Again, this is a great stay, it just needs a little more equipment to make it perfect."

A verified traveller stayed at Colorful beach cottage w/ heated private pool & grill area - dog-friendly

Posted 1 month ago

Explore a world of travel with Expedia

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?

Charming Bungalow with Fabulous Location and Private Pool!: This highly rated holiday home rental in Anna Maria is located near the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games. Other favourite homes for rent in Anna Maria are Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear and Beachfront - New Listing!.

How many holiday rentals are there in Anna Maria?

With 777 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.

Unlock instant savings with Member Prices

Search Holiday Rentals in Anna Maria

Check prices for these dates

Top Holiday Rentals in Anna Maria

Charming cottage in quiet area, close to beach & bay.

Charming Bungalow with Fabulous Location and Private Pool!

Beachfront Home | Pool + Spa | Games | Ocean Views

Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

Beachfront - New Listing!

Charming cottage located close to beach - private heated pool

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

Adorable Beach cottage just steps Bean Point beach!

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Near Bean Point!! Short stays available! Heated Pool

⚓Mermaid Sunrise! Available for Summer! Coastal beach home w/pool 200 steps to beach!⚓

A Bay From It All: Private backyard oasis, steps to Bay, Bean Point

Casa Amiga managed by Beach Retreats FL Anna Maria Island

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

Bridgeview: Bay front with sweeping views, sleeps 12!

The Wee Cottage | House in Anna Maria

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

Find out more about Anna Maria

Recent reviews of Anna Maria properties

Charming cottage in quiet area, close to beach & bay.

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

Charming cottage located close to beach - private heated pool

Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

A Bay From It All: Private backyard oasis, steps to Bay, Bean Point

Charming Bungalow with Fabulous Location and Private Pool!

Bridgeview: Bay front with sweeping views, sleeps 12!

Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

Explore a world of travel with Expedia

Trending destinations on Expedia.co.uk

Frequently asked questions