Holiday Rentals in Anna Maria

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Holiday Rentals in Anna Maria

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

10.0 out of 10, Exceptional, (117)
"Everything about our stay was amazing. You can tell the owners care about quality, from all the utensils in the kitchen to the living room area furniture. . We all had a blast. "
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

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

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

AMI North End Private Heated Pool. 1.2 blocks to beach!

10.0 out of 10, Exceptional, (135)
"Absolutely best experience visiting a new island. Close to beach, quiet, clean and great amenities and communication. The pool felt great and we enjoyed our stay. Thanks so much!"
AMI North End Private Heated Pool. 1.2 blocks to beach!

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

9.8 out of 10, Exceptional, (276)
"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.

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

10.0 out of 10, Exceptional, (269)
"Great Place We will be back Thank You! Dave and Kathy"
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR/1BA Anna Maria - By Island Real Es

9.6 out of 10, Exceptional, (21)
"We had a fantastic stay at Hidden Oasis. Beautiful place right on the beach!"
Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR/1BA Anna Maria - By Island Real Es

Near Bean Point!! Short stays available! Heated Pool

9.6 out of 10, Exceptional, (47)
"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

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

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (56)
"Nice property,, the location is walking distance to restaurants, and across the street from beach access. We would definitely stay at this property again!"
Adorable Beach cottage just steps Bean Point beach!

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

9.4 out of 10, Exceptional, (125)
"Amazing time. Wonderful set up, CLEAN, GREAT pool and hot tub. Great host to communicate with as well. 3 min walk to the beach. Sand toys plenty of pool towels and linens. Very accommodating, would recommend anyone to stay here! "
The price is €1,050
includes taxes & fees
1 Aug - 2 Aug
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

Stylish bayside condo with WiFi & pool - close to the beach & restaurants

9.6 out of 10, Exceptional, (91)
"Great property ,,clean and well equipped steps to the beach "
The price is €285
includes taxes & fees
28 Jul - 29 Jul
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

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

9.8 out of 10, Exceptional, (119)
"This property was amazing! Exactly like the listing! Very clean and comfortable with everything you could need! The location is also great. The best breakfast and lunch place on the island is a 2 minute walk to the corner and there are also many other restaurants within walking distance. A beautiful beach only a block away. What more could you ask for? "
Ideal Location, Stunning Villa! Close to beach, beach gear provided!

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!

Dog-friendly home with amazing backyard, pool, spa, putting green & game room

9.0 out of 10, Wonderful, (19)
"This house is on a great neighborhood on the north end of the island. The one draw back at the moment is the beach you are walking distance to is closed due to the hurricane. The back yard is cute, but you can't heat the hot tub up. "
Dog-friendly home with amazing backyard, pool, spa, putting green & game room

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

9.8 out of 10, Exceptional, (86)
"Excellent place for relaxing beach vacation"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation

9.8 out of 10, Exceptional, (24)
"Really enjoyed the stay. The bikes made a great addition."
Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation

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

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

Charming Bungalow with Fabulous Location and Private Pool!

9.8 out of 10, Exceptional, (159)
"The location is just a block from the beach and lots of unique restaurants. The pool area is great!"
The price is €741
includes taxes & fees
27 Jul - 28 Jul
Charming Bungalow with Fabulous Location and Private Pool!

Bridgeview: Bay front with sweeping views, sleeps 12!

9.8 out of 10, Exceptional, (40)
"I would definitely recommend or stay here again"
Bridgeview: Bay front with sweeping views, sleeps 12!

Charming house with private heated pool, lanai. Great location to beach & shops

10.0 out of 10, Exceptional, (160)
"Everything was great! We enjoyed the pool, screen porch, location to beach and restaurants. The owners were friendly and easy to communicate with. We will be back for 2 weeks next time. "
Charming house with private heated pool, lanai. Great location to beach & shops
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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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 Home | Pool + Spa | Games | Ocean Views.

How many holiday rentals are there in Anna Maria?

With 784 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.