Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (57)
"This house was perfect for our family of 4. Loved the open concept. The small pool was refreshing and the location was amazing - so close to the most beautiful section of the beach. We will be back! "
The price is NZ$1,535
includes taxes & fees
22 July - 23 July
Adorable Beach cottage just steps Bean Point beach!

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

10.0 out of 10, Exceptional, (178)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

10.0 out of 10, Exceptional, (86)
"We have stayed in this house a couple of times and love the location the food, shopping and the beach! The backyard oasis is perfect for lounging after a day at the beach. Frankie is fabulous to work with and keeps the property in beautiful condition. Would certainly recommend!"
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

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

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

10.0 out of 10, Exceptional, (270)
"Family of 4 stayed here comfortably for 3 nights in April. Had an excellent time on the island. And we were really impressed with the property and its location. Cool little trail, steps from the door take you straight to Bean Point."
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

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

9.8 out of 10, Exceptional, (87)
"Excellent place for relaxing beach vacation"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Escape to Anna Maria Island!

10.0 out of 10, Exceptional, (117)
"Our stay was fantastic. Easy walking access to the beach, trolley and restaurants. "
Escape to Anna Maria Island!

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

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

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

9.4 out of 10, Exceptional, (128)
"Our family had a wonderful time here for spring break. The pool was especially nice because the wading area was perfect for our 2 year old to play with water toys. And we had a very short walk to the beach at Bean Point, which was lovely. The beds were very comfortable and the kitchen was supplied with everything we needed. We rented an electric golf cart, which was easily charged at the outdoor outlet. Also, we appreciated the pack and play, the beach wagon, beach chairs, and pool toys....
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

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

9.8 out of 10, Exceptional, (278)
"This house was perfect! Close to the beach and restaurants. It had everything we needed. The fenced in backyard was great for our dog. We would definitely stay here again. "
Charming cottage in quiet area, close to beach & bay.

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

9.8 out of 10, Exceptional, (56)
"We had an amazing stay! Can’t wait to return!"
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

Ideal Location, Stunning Villa! Close to beach, beach gear provided!

9.8 out of 10, Exceptional, (121)
"Really cute place and the location was prime. "
Ideal Location, Stunning Villa! Close to beach, beach gear provided!

Near Bean Point!! Short stays available! Heated Pool

9.6 out of 10, Exceptional, (48)
"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."
Near Bean Point!! Short stays available! Heated Pool

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

9.6 out of 10, Exceptional, (180)
"My family loved staying here during our week in Anna Maria! Great location close to Pine and we loved having our own little beach. We would definitely stay again!"
The price is NZ$1,577
includes taxes & fees
29 July - 30 July
AUGUST SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

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

9.0 out of 10, Wonderful, (13)
"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...

Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!

9.8 out of 10, Exceptional, (157)
"The house is really cute and cozy as advertised. Loved to stay on there. Had everything we needed."
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!

Best location on the island. Private dock, steps to Anna Maria Beach and Pier

9.8 out of 10, Exceptional, (66)
"We'll certainly be back to this beautiful Condo! Amaizing location!"
Best location on the island. Private dock, steps to Anna Maria Beach and Pier

Aloha Fern: North End Beach House, Pool by Anna Maria Life Vacation Rentals

9.8 out of 10, Exceptional, (22)
"Had a great stay here! Clean place with plenty of kitchen hardware, 2 blocks to beach and close to everything else "
Aloha Fern: North End Beach House, Pool by Anna Maria Life Vacation Rentals

Wave n Sea - Close to the Beach with Pool - Anna Maria Island - By Island Real E

9.4 out of 10, Exceptional, (16)
"This home was absolutely beautiful! Everything was very clean, nicely taken care of, and the backyard and pool were fantastic. It was walking distance to lots of great shops and even to the beach, which was fantastic. We would definitely be back!"
Wave n Sea - Close to the Beach with Pool - Anna Maria Island - By Island Real E

Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches

9.6 out of 10, Exceptional, (85)
"It was better than we even expected, especially knowing that both Hurricane Helene and Milton had affected this property only a few short months before our stay. It was a very restful and comfortable surrounding for us. It was just a short walk to a beautiful beach. We would like to come back again."
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches
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

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?

Adorable Beach cottage just steps Bean Point 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 Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue! and 🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬.

How many holiday rentals are there in Anna Maria?

With 786 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.