An aerial view of a coastal town with a long pier extending into turquoise waters.

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Dates

November 2026

December 2026

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Our top choices for Anna Maria Island villas

A multi-story hotel with a pool, beachside location, and a parking area.

1. Coconuts 107 ~ Gulf Front ~ Shared Pool

Holmes Beach

Zulett L.

A resort with a pool, beach access, and a view of the ocean.

2. Beachfront · Heated Pool · King Bed

Holmes Beach

￥114,758 total

includes taxes & fees

Dec 1 - Dec 2

A house with a turquoise door, a welcome sign, and a window with blinds.

3. Peaceful Villa, 3.3 mi to the Beach & Big Parking

Bradenton

Shanna Lee

￥68,116 total

includes taxes & fees

Nov 10 - Nov 11

A single-story house with a white exterior, a dark roof, and a front door.

4. Lakefront 2BR Bradenton Rental Near IMG & Beaches

South Bradenton

Laura

￥36,313 total

includes taxes & fees

Nov 18 - Nov 19

A modern single-story house with a paved driveway, a basketball hoop, and a well-maintained lawn.

5. HeatedPool • HotTub • OutdoorKitchen/Theater/Games

South Bradenton

Alisha M.

￥94,389 total

includes taxes & fees

Nov 10 - Nov 11

A serene lakeside setting with large trees and a white gazebo.

6. Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Bradenton

Kay S.

￥46,470 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with a table and chairs, a green wall with a sign, and a view of palm trees and greenery.

7. Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

Bradenton

Kara H.

￥46,470 total

includes taxes & fees

Nov 10 - Nov 11

A resort with a swimming pool, a covered patio, and a view of the ocean.

8. Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Bradenton

Terri B.

￥46,470 total

includes taxes & fees

Nov 10 - Nov 11

A bicycle parked outside a building with a 'Hello' mat at the entrance.

9. [Beach Elements] pool view withprivate beach access

Siesta Key

Natalie M.

￥46,928 total

includes taxes & fees

Nov 15 - Nov 16

A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

10. Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Sarasota

Jennie A.

￥58,332 total

includes taxes & fees

Nov 17 - Nov 18

An outdoor kitchen with a grill, cooking utensils, and a view of lush greenery.

11. Heated Pool • Sleeps 25 • Pickle/Bball • Theater

Bradenton

Adam D.

￥138,674 total

includes taxes & fees

Nov 11 - Nov 12

A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

12. SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

Sarasota

Sharon M.

￥78,348 total

includes taxes & fees

Nov 8 - Nov 9

13. 3-bedroom villa in enchanting St. Petersburg with AC comfort

Childs Park

￥69,830 total

includes taxes & fees

Nov 7 - Nov 8

14. BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

Sarasota

Misty S.

￥83,137 total

includes taxes & fees

Nov 5 - Nov 6

A balcony with a table set for breakfast, including croissants, fruit, and coffee, with a city view in the background.

15. Beachside Bliss | Rooftop Gulf Views & Fun Vibes

Madeira Beach

Dr Rachael M.

￥156,697 total

includes taxes & fees

Nov 8 - Nov 9

A balcony with wicker furniture and a view of the ocean at sunset.

16. 180° Oceanfront 3BR Condo w/ Pool

Madeira Beach

Ann N.

￥95,101 total

includes taxes & fees

Nov 8 - Nov 9

A covered outdoor seating area with a round table and chairs, surrounded by lush tropical vegetation.

17. Miramar

Siesta Key

View all properties

Learn more about Anna Maria Island

Pristine white beaches and turquoise waters beckon you to this laid-back Gulf Coast paradise. Rent a bike to explore charming Pine Avenue, then watch the sunset at Bean Point's secluded shore.

See all hotels in Anna Maria Island

Top reviews in Anna Maria Island

A balcony with a dining table set for breakfast, overlooking a swimming pool and a marina.

Waterline Villas & Marina, Autograph Collection

Holmes Beach

10/10 Excellent

LORRIE

A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.

Carlisle Inn

Pinecraft

10/10 Excellent

Rebecca

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the water.

Compass Hotel by Margaritaville Anna Maria Sound

Bradenton

10/10 Excellent

Francisco

A balcony with a view of a beach, a palm tree, and a clear sky.

Seaside at Anna Maria Island Inn

Bradenton Beach

10/10 Excellent

Daniel

A hotel with a pool, lounge chairs, and a view of the ocean.

Anna Maria Beach Resort

Holmes Beach

10/10 Excellent

Edward

A wooden balcony with a view of a beach, palm trees, and beach chairs.

Cedar Cove Resort and Cottages

Holmes Beach

10/10 Excellent

Dwag

A couple toasting with champagne glasses on a balcony with a pool view.

Hollander Boutique Hotel

Downtown St. Petersburg

10/10 Excellent

Paul

A hotel entrance with a red and yellow sign, palm trees, and a parking lot.

Home2 Suites Sarasota I-75 Bee Ridge, FL

Sarasota

10/10 Excellent

Marcus

A pool area with glass barriers, lounge chairs, and pink umbrellas.

The Saint Hotel

St. Pete Beach

10/10 Excellent

When my grandma and I first came we were greeted when we went to check in with free drinks and then room service always ensured we had water. Property has free taxi rides that work on tips. Bikes, beach chairs, beach loungers, umbrella. I think the only thing I wish the hotel had would be more food options at 82 degrees restaurant other than that the staff was super friendly and we would definitely stay here again and recommend this place to our family and friends.

Leyla

A white building with a flat roof, a door, and windows with green shutters.

Pelican Post at Anna Maria Island Inn

Bradenton Beach

10/10 Excellent

My husband and I have stayed at the pelican Post many times but this was our first visit after hurricane Helene and Milton. We were SO HAPPY to see that the hotel look just as good as it did before! The booking process was smooth and thanks to the girl who checked us in, our stay was made even better! She was very sweet and welcomed us back as returning customers! Our interaction with her was wonderful, so if you are reading this Janelle, thanks again – you’re the best! And kudos to the owners...

Maria

A rooftop lounge with white furniture, a glass balustrade, and a view of the ocean at sunset.

Ocean Club Treasure Island Hotel

Sunshine Beach

10/10 Excellent

Kimberly

A residential area with houses, a swimming pool, and a sign indicating 'Twin Palms 1115'.

Twin Palms at Siesta

Siesta Key

10/10 Excellent

The room was very comfortable and clean. Checking in was a breeze. The kitchenette is perfect for cooking and just enough space for two people. The bed was comfortable. The bathroom was very clean. Very home-like feeling. The room was a very nice stroll away from Siesta Key beach which is so lovely. There is a heated pool which was very nice when it was windy outside. All in all, it is a great place to stay for a relaxing time. Small grocery, restaurant and bar all in walking distance.

Monique

A white chair in a covered outdoor area with arched windows overlooking a garden with various plants and trees.

Crystal Bay Historic Hotel

La Vista

10/10 Excellent

This hotel definately exceeded our expectations. Even though it is an old building (built in the early 1900s), the staff is very proud of its heritage and previous famous guests. They have done an outstanding job renovating and upkeeping this place. The hotel areas and rooms were impecably clean and the ambiance was from an old high vintage high class hotel. But the most noteworthy thing was their outstanding customer service. They treated us like family from the moment we checked in up to a...

Luis

A hotel with a swimming pool, palm trees, and a parking lot.

Coral Pointe Sarasota, an Ascend Collection Hotel

Fruitville

10/10 Excellent

The hotel is beautifully decorated. Its very clean from the lobby to the room. The room was spotless, the beds were comfortable and they supply shampoo, conditioner and body wash in their bathrooms. The breakfast was very good. They offer hot food i.e. eggs, sausage, bacon, french toast or pancakes. They also have cereals, oatmeal, fruits and yogurt. The pool was another wonderful feature, clean and heated with plenty of chairs and tables. The staff was super friendly and very helpful. There are...

Ester

Hampton Inn & Suites Bradenton Downtown Historic District

Downtown Bradenton

10/10 Excellent

Shari

A Hampton Inn & Suites hotel with a modern design, featuring a parking lot and palm trees.

Hampton Inn & Suites Sarasota/Lakewood Ranch

Bradenton

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

What are the best villas in Anna Maria Island?

Anna Maria Island offers multiple villas with a total average guest review rating of 0. Organizing a visit to Bradenton Beach? Bridge 2 Bradenton Beach - 1 Bedroom Hotel Room is a highly recommended 3-star option that features a terrace and an oven. Another favorite pick is Bridge 7 Bradenton Beach - 2 Bedroom Hotel Room. It has a 3-star rating and conveniences that include a terrace and WiFi.

What are the best cheap villas in Anna Maria Island?

That depends on which corner of Anna Maria Island you're hoping to visit. If you're headed to Bradenton Beach, Bridge 4 Bradenton Beach - 1 Bedroom Hotel Room is a popular pick. This low-priced property includes a terrace and an oven. Making a stop in Holmes Beach? Bridge 4 Bradenton Beach - 1 Bedroom Hotel Room is an affordable option in this city. A terrace and WiFi are two of the conveniences at this stay. Villas start at just ￥15,865 per night, which means your vacation won't make a big dent in your finances! If you'd like to hold on to your hard-earned money and still enjoy the best of Anna Maria Island, add some fantastic free attractions to your must-do list. Anna Maria Beach and Coquina Beach are always great choices. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your villa in Anna Maria Island with Expedia?

Use Expedia to find your ideal villa in Anna Maria Island. Taking the kids on a break? Use our handy filters to search for stays with a pool or free WiFi. If you're on a budget, click on how much you'd like to spend and the star rating of the property. We'll help you find the right stay in tune with your style and taste.

How can I find cheap villas in Anna Maria Island?

An excellent way to score cheap villas in Anna Maria Island is with Expedia's handy filter tool. Fine-tune your search results by budget, star rating and amenities to find unbeatable rates in only a couple of clicks.

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Anna Maria Island Vacation Rentals
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Search Villas in Anna Maria Island

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Anna Maria Island villas

1. Coconuts 107 ~ Gulf Front ~ Shared Pool

2. Beachfront · Heated Pool · King Bed

3. Peaceful Villa, 3.3 mi to the Beach & Big Parking

4. Lakefront 2BR Bradenton Rental Near IMG & Beaches

5. HeatedPool • HotTub • OutdoorKitchen/Theater/Games

6. Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

7. Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

8. Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

9. [Beach Elements] pool view withprivate beach access

10. Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

11. Heated Pool • Sleeps 25 • Pickle/Bball • Theater

12. SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

13. 3-bedroom villa in enchanting St. Petersburg with AC comfort

14. BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

15. Beachside Bliss | Rooftop Gulf Views & Fun Vibes

16. 180° Oceanfront 3BR Condo w/ Pool

17. Miramar

Learn more about Anna Maria Island

Top reviews in Anna Maria Island

Waterline Villas & Marina, Autograph Collection

10/10 Excellent

Frequently Asked Questions

What are the best villas in Anna Maria Island?

What are the best cheap villas in Anna Maria Island?

Why book your villa in Anna Maria Island with Expedia?

How can I find cheap villas in Anna Maria Island?

Explore a world of travel with Expedia