Anna Maria Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Anna Maria

Love Shack on the Water Most desirable location on AMI

Anna Maria
10.0 out of 10, Exceptional, (39)
"Great spot for our last minute vacation! Beautiful views and short walk to anything up Pine Avenue and to the beaches. The place is as nice as pictured. Would definitely stay again!"
United States
Laura H.
Love Shack on the Water Most desirable location on AMI

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Anna Maria
9.8 out of 10, Exceptional, (69)
"Perfect home for a family getaway "
United States
Michael M.
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Bayfront Escape with Stunning Water Views and Steps to Bean Point

Anna Maria
9.4 out of 10, Exceptional, (12)
"Very nice property with a great view great location "
United States
Gerry C.
Bayfront Escape with Stunning Water Views and Steps to Bean Point

CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley, Dog*(See Note) Friendly!

Anna Maria
8.8 out of 10, Excellent, (51)
"Second time staying in this great location one block from Rod and Reel pier at bean point. Cute place with a great little pool."
United States
Katrina F.
CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley, Dog*(See Note) Friendly!

Charming cottage located close to beach - Private heated pool!

Anna Maria
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Summer J.
Charming cottage located close to beach - Private heated pool!

NEW! Meet Me At Sunset! 3 Homes from the Beach!

2.5 star property
Anna Maria
The price is NZ$2,919
includes taxes & fees
30 Nov - 1 Dec
NEW! Meet Me At Sunset! 3 Homes from the Beach!

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

Anna Maria
9.2 out of 10, Wonderful, (24)
"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."
United States
Travis N.
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi & Trolley

Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Anna Maria
9.4 out of 10, Exceptional, (43)
"Great location, great people, awsome hosts, very prompt and caring. "
United States
Alban K.
Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Anna Maria
9.2 out of 10, Wonderful, (56)
"We absolutely enjoyed staying here and will be back. "
United States
Allie S.
The price is NZ$737
includes taxes & fees
10 Nov - 11 Nov
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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

Anna Maria
9.8 out of 10, Exceptional, (293)
"We thoroughly enjoyed our time at this lovely home. It was located in near multiple excellent restaurants and rental stores and was within walking distance to Bean Beach. The place was clean and had all the amenities needed to make our stay perfect and memorable. "
United States
Angeline T.
Charming cottage in quiet area, close to beach & bay.

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

Anna Maria
9.6 out of 10, Exceptional, (190)
"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. "
United States
Andre P.
The price is NZ$1,425
includes taxes & fees
16 Nov - 17 Nov
NOVEMBER SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Luxury Upscale Beach Home Gulf of Mexico, Private Heated Pool/Spa. Opt. Golfcart

Anna Maria
10.0 out of 10, Exceptional, (126)
"Always enjoy stay at this location. Easy access to everything, good communication if any issues and an extremely short walk to the beach."
United States
Shawn M.
Luxury Upscale Beach Home Gulf of Mexico, Private Heated Pool/Spa. Opt. Golfcart

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

Anna Maria
9.8 out of 10, Exceptional, (104)
"Wonderful"
United States
Rokelle L.
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

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

Anna Maria
9.4 out of 10, Exceptional, (136)
"Great property! Close to the beach and the pool was fantastic! Rooms were spacious and the beds were comfortable. Kitchen was very nice as well and had everything you could want including an air fryer. House was clean and we enjoyed our stay."
United States
Hannah B.
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

Beaches and Dreams: Ultimate Luxury Beachfront Paradise

Anna Maria
10.0 out of 10, Exceptional, (18)
"Everything was great. We will book again."
United States
Chad S.
Beaches and Dreams: Ultimate Luxury Beachfront Paradise

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

3.0 star property
Anna Maria
9.6 out of 10, Exceptional, (16)
"Wonderful visit, an excellent venue for a family. Fantastic pool area, with sunshine all day. Enjoyable gulf views.Clean and inviting home."
United States
Jon M.
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt

Anna Maria
10.0 out of 10, Exceptional, (3)
"Beautiful place, host is very responsive and overall fantastic to work with. We had a great time! "
United States
Heather W.
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt

CHRISTMAS available! New Breathtaking Canal front Home on Best street in AMI!

Anna Maria
10.0 out of 10, Exceptional, (4)
"A great house,l highly recommend it "
United States
Jonas D.
CHRISTMAS available! New Breathtaking Canal front Home on Best street in AMI!

Cozy Barefoot Bungalow: Steps to Bayfront Park & Bean Point, Pet-Friendly!

Anna Maria
10.0 out of 10, Exceptional, (2)
"I can’t say enough amazing things about this home. Newly renovated, stylish, very clean, homey and comfortable. Short walk to the beach and a short drive to the shops. Stay, I promise you won’t regret it! "
United States
Tracey S.
Cozy Barefoot Bungalow: Steps to Bayfront Park & Bean Point, Pet-Friendly!

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

Anna Maria
10.0 out of 10, Exceptional, (117)
"Our first time to Anna Maria Island and it was amazing! The house was perfect for our little family."
United States
Angela H.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Anna Maria Hotel Reviews

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, 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 NZ$737 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?

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach: This highly rated holiday home rental in Anna Maria is located near the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Anna Maria are Bayfront Escape with Stunning Water Views and Steps to Bean Point and CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley, Dog*(See Note) Friendly!.

How many holiday rentals are there in Anna Maria?

With 810 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.