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Top Holiday Rentals in Anna Maria

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

10.0 out of 10, Exceptional, (275)
"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!

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 £1,015
includes taxes & fees
24 Aug - 25 Aug
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

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

9.8 out of 10, Exceptional, (165)
"The location is just a block from the beach and lots of unique restaurants. The pool area is great!"
The price is £594
includes taxes & fees
18 Aug - 19 Aug
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

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 £989
includes taxes & fees
18 Aug - 19 Aug
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (58)
"Our family of 6enjoyed our stay!"
The price is £678
includes taxes & fees
19 Aug - 20 Aug
Adorable Beach cottage just steps Bean Point beach!

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

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

10.0 out of 10, Exceptional, (180)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

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

9.6 out of 10, Exceptional, (182)
"Great location. Private beach with great sun rise view. Close to local shops and restaurants "
The price is £710
includes taxes & fees
28 Aug - 29 Aug
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

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

9.4 out of 10, Exceptional, (50)
"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

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

9.6 out of 10, Exceptional, (37)
"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, (11)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

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

9.0 out of 10, Wonderful, (44)
"Second time staying in this great location one block from Rod and Reel pier at bean point. Cute place with a great little pool."
CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...

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

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

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

9.2 out of 10, Wonderful, (15)
"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...

Escape to Anna Maria Island!

10.0 out of 10, Exceptional, (118)
"Our stay was fantastic. Easy walking access to the beach, trolley and restaurants. "
Escape to Anna Maria Island!

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

10.0 out of 10, Exceptional, (1)
"This property was very clean and convenient to everything! We could Walker one street over to the beach or drive our golf cart over easily. The communication was great even when there was a small problem they came out quickly to take care of things. I would absolutely come back and stay again! "
⚓Mermaid Sunrise! Coastal beach home w/pool 200 steps to beach!⚓

Luxury beachfront home with private pool, putting green, golf cart and bikes!

9.2 out of 10, Wonderful, (64)
"This house was perfect! The pool was warm. We had dolphins and a manatee who swam by the house many times during our stay. The sunrise is amazing! Location is perfect away from the busy resorts. Would rent again! "
Luxury beachfront home with private pool, putting green, golf cart and bikes!
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?

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 Adorable Beach cottage just steps Bean Point beach! and Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!.

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.