Holiday Rentals in Anna Maria

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Holiday Rentals in Anna Maria

Our top choices for Anna Maria holiday rentals

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

9.4 out of 10, Exceptional, (3)
"Well maintained propert and enjoyed our stay."
The price is €1,165
includes taxes & fees
7 Sept - 8 Sept
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!

10.0 out of 10, Exceptional, (276)
"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!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (119)
"Such a beautiful property! We can't wait to go back!"
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

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

10.0 out of 10, Exceptional, (1)
"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...
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

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

The price is €1,155
includes taxes & fees
1 Sept - 2 Sept
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (59)
"Perfect home for a family getaway "
Adorable Beach cottage just steps Bean Point beach!

SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (184)
"Great location. Private beach with great sun rise view. Close to local shops and restaurants "
The price is €663
includes taxes & fees
17 Sept - 18 Sept
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

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

10.0 out of 10, Exceptional, (181)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

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

9.8 out of 10, Exceptional, (96)
"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 "
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

Near Bean Point!! Short stays available! Heated Pool

9.6 out of 10, Exceptional, (51)
"Good property with access to the beach "
Near Bean Point!! Short stays available! Heated Pool

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

9.4 out of 10, Exceptional, (38)
"Dolphins everyday. Great spot. Can’t really think of any negatives. Really a nice place."
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

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

3.0 star property
9.4 out of 10, Exceptional, (12)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

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

9.0 out of 10, Wonderful, (16)
"Easy to rent. Great location to the beach, shopping and food."
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...

Beachfront Home | Pool + Spa | Games | Ocean Views

10.0 out of 10, Exceptional, (38)
"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!"
Beachfront Home | Pool + Spa | Games | Ocean Views

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

9.8 out of 10, Exceptional, (56)
"Great place "
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...

9.0 out of 10, Wonderful, (45)
"The house was great for our family, clean and with everything that we needed available. The pool was always clean. Location was great. "
CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...

Beachfront - New Listing!

10.0 out of 10, Exceptional, (26)
"The Diamond Star has it all! The kitchen is fully stocked, and they provide everything you need for a day at the beach. There are tons of games for family! The house is immaculate, and the location is fantastic! We were able to walk to get ice cream, dinner, and breakfast effortlessly. Our family loved the pool and watching the sunsets from the decks! Nicole was a wonderful host, going above and beyond to ensure we had everything we needed! "
Beachfront - New Listing!

September Golf Cart Special

10.0 out of 10, Exceptional, (40)
"Amazing stay in an amazing property. The pictures can’t do the view justice, truly amazing."
September Golf Cart Special

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

10.0 out of 10, Exceptional, (231)
"Excellent views of the beach, ocean and sunsets! Wonderful vacation home!!! "
Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Perfect Anna Maria-20% off Aug/Sep 3 blocks to sugar sand beach. Heated pool.

10.0 out of 10, Exceptional, (114)
"This home was perfect for our family getaway to Anna Maria. It is clean, close to the beach and the pool with the view of the canal was wonderful. Margeret and Jim were quick to respond to any communication prior to our arrival as well as during our stay. Would definitely stay again! Delightful :)"
Perfect Anna Maria-20% off Aug/Sep 3 blocks to sugar sand beach. 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

Find out more about Anna Maria

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 €663 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. 

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?

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!: This highly rated holiday home rental in Anna Maria offers an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite homes for rent in Anna Maria are Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat and Adorable Beach cottage just steps Bean Point beach!.

How many holiday rentals are there in Anna Maria?

With 780 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.