Vacation rentals in Anna Maria

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Top-rated vacation rentals in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Condo in Bradenton
Minutes to Anna Maria + Canal Hangout Onsite
Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.
Dec 4 – 11
$109 per night
4.93 out of 5 average rating, 58 reviews
Guest favorite
Home in Anna Maria
Private 30' Pool and Boat Dock - Rated best on AMI
* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!
Dec 19 – 26
$570 per night
4.93 out of 5 average rating, 152 reviews
Guest favorite
Home in Holmes Beach
Sea AMI
This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.
Aug 18 – 25
$284 per night
4.96 out of 5 average rating, 157 reviews

Popular amenities for Anna Maria vacation rentals

Stay near Anna Maria's top sights

Bean Point Beach67 locals recommend
The Sandbar Restaurant168 locals recommend
Rod and Reel Pier111 locals recommend
The Waterfront Restaurant99 locals recommend
The Donut Experiment66 locals recommend
Two Scoops26 locals recommend

Other great vacation rentals in Anna Maria

Guest favorite
Home in Anna Maria
ami skyview
Dec 12 – 19
$875 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Home in Anna Maria
Island in the Sun
May 13 – 20
$548 per night
4.92 out of 5 average rating, 36 reviews
Guest favorite
Home in Anna Maria
SunKissed Cottage
Aug 21 – 28
$918 per night
4.87 out of 5 average rating, 23 reviews
Guest favorite
Home in Holmes Beach
True beach front home - 3 beds/2 bath, heated pool
Jan 6 – 13
$671 per night
4.95 out of 5 average rating, 37 reviews
Guest favorite
Home in Anna Maria
Amie House Chef’s kitchen Fun pool - walk to beach
Nov 16 – 23
$944 per night
5.0 out of 5 average rating, 28 reviews
Guest favorite
Guest suite in Bradenton
King Bed Stunning Beach Retreat in great area!
Oct 2 – 9
$95 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Anna Maria
Anna Maria Chateau. Private Pool home
Aug 30 – Sep 6
$771 per night
4.96 out of 5 average rating, 23 reviews
Guest favorite
Home in Anna Maria
My Private Beach
Jan 18 – 25
$995 per night
4.96 out of 5 average rating, 52 reviews
Guest favorite
Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
Dec 5 – 12
$350 per night
4.88 out of 5 average rating, 34 reviews
Guest favorite
Condo in Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
Sep 8 – 15
$364 per night
4.99 out of 5 average rating, 89 reviews
Guest favorite
Apartment in Anna Maria
Quaint 2 BR/1B, a few houses from the beach
Sep 10 – 17
$175 per night
4.97 out of 5 average rating, 32 reviews
Guest favorite
Home in Anna Maria
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Sep 7 – 14
$678 per night
5.0 out of 5 average rating, 57 reviews

Quick stats about vacation rentals in Anna Maria

Total rentals

830 properties

Rentals with a pool

670 properties have a pool

Pet-friendly rentals

270 properties allow pets

Family-friendly rentals

770 properties are a good fit for families

Total number of reviews

10K reviews

Nightly prices starting at

$10 before taxes and fees

Frequently Asked Questions

  • How is the weather in Anna Maria?

    Anna Maria experiences a tropical climate with warm, humid summers that generally reach 90°F (32°C) and mild winters hovering around 70°F (21°C). Rainfall is most common in the summer months, while winter remains relatively dry.

  • What are some of the best things to do in Anna Maria?

    Popular activities in Anna Maria include beachcombing, exploring the local dining scene, boating, fishing, and bird watching. For those interested in culture, visiting Island Gallery West, a co-op of local artists, is often recommended.

  • What is the best time of year to visit Anna Maria?

    The most popular time to visit Anna Maria is from February to May when the weather is warm and dry. During this time, the island hosts the Anna Maria Island Art League Springfest in March and the Food and Wine on Pine event in May, attracting many visitors.

  • What are the best places to stay in Anna Maria?

    Popular areas to stay in Anna Maria include the bustling Holmes Beach area, the serene Bean Point neighborhood, or the city center near Pine Avenue for its proximity to shops and restaurants. The Bradenton Beach area is also frequently suggested for its lively atmosphere and beachfront properties.

  • What are the best places to visit in Anna Maria?

    Frequently suggested places to visit include the historic Anna Maria City Pier, Bean Point Beach for its tranquil atmosphere, and the island town of Bradenton Beach. The Anna Maria Island Historical Museum is popular for those interested in local history.

  • What are some hiking trails in Anna Maria?

    Though Anna Maria is known more for its beaches, lovers of the outdoors can take a leisurely walk along the Coquina Baywalk at Leffis Key, a trail with abundant wildlife. The Robinson Preserve in nearby Bradenton, a 15-minute drive away, also has numerous walking and biking trails.

  • What are some family activities to do in Anna Maria?

    Families often enjoy exploring the Anna Maria Island Historical Society to learn about the area's past, embarking on dolphin watching tours, or spending a day at Bayfront Park, a beachfront area with a playground and picnic spots. Another frequently suggested activity is visiting the Island Gallery West, a local artist co-op.

  • What are some of the best day trip ideas in Anna Maria?

    A day trip to the nearby city of Bradenton, just 10 miles (16 km) away, is often recommended for its rich history and vibrant arts scene. Alternatively, you could explore the De Soto National Memorial, about 7 miles (11 km) away, or venture further to Tampa, 60 miles (96 km) away, known for its exciting theme parks.

  • Are there pet-friendly vacation rentals in Anna Maria?

    Four-legged friends are welcome in Anna Maria. Choose from more than 270 vacation rentals for guests traveling with pets.

  • Do house rentals in Anna Maria have free parking?

    Absolutely! We offer over 520 house rentals with free parking in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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