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

Search Villas in Anna Maria Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Anna Maria Island villas

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

1. NEW!~ Beach Front/Heated Pool! Coconuts 107

NEW!~ Beach Front/Heated Pool! Coconuts 107
Holmes Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great property, location and host …worth the price. Enjoy your stay as much as we did !!"
United States
Zulett L.
The price is ￥67,068
￥111,733 total
includes taxes & fees
Nov 1 - Nov 2
NEW!~ Beach Front/Heated Pool! Coconuts 107
A single-story house with a white exterior, a dark roof, and a front door.

2. Lakefront 2BR Bradenton Rental Near IMG & Beaches

Lakefront 2BR Bradenton Rental Near IMG & Beaches
South Bradenton
8.8 out of 10, Excellent, (3 reviews)
"Very clean. No tissues or napkins🤔. Recommend pump hand soap instead of little bars. Also, 2 outdoor chaises were ripped and 1 out of 2 outdoor chairs was broken and unable to use the.."
United States
Laura
The price is ￥16,182
￥38,216 total
includes taxes & fees
Oct 28 - Oct 29
Lakefront 2BR Bradenton Rental Near IMG & Beaches
A serene lakeside setting with large trees and a white gazebo.

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

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
Bradenton
9.8 out of 10, Exceptional, (30 reviews)
"The host was welcoming, and the amenities were great. We liked staying in that part of town."
United States
Perry W.
The price is ￥20,264
￥46,702 total
includes taxes & fees
Oct 9 - Oct 10
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
A resort with a swimming pool, a covered patio, and a view of the ocean.

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

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
Bradenton
10.0 out of 10, Exceptional, (39 reviews)
"This was a great place to stay. Easy access to everything the area has to offer."
United States
Terri B.
The price is ￥20,264
￥46,386 total
includes taxes & fees
Oct 10 - Oct 11
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
A dining area with a table and chairs, a green wall with a sign, and a view of palm trees and greenery.

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

Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
Bradenton
10.0 out of 10, Exceptional, (39 reviews)
"Very nice place and quiet. Enjoyed the secluded pool and the variety of plants and flowers everywhere. The Riverwalk was nice too."
United States
Craig C.
The price is ￥20,287
￥46,281 total
includes taxes & fees
Oct 16 - Oct 17
Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
A bicycle parked outside a building with a 'Hello' mat at the entrance.

6. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (43 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is ￥14,484
￥44,188 total
includes taxes & fees
Oct 13 - Oct 14
[Beach Elements] pool view withprivate beach access
A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

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

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Sarasota
9.6 out of 10, Exceptional, (27 reviews)
"Excellent stay. Very clean and facilities were great "
United Kingdom
Jennie A.
The price is ￥23,890
￥63,564 total
includes taxes & fees
Oct 10 - Oct 11
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
A residential property with a driveway leading to a house, surrounded by well-maintained lawns and large trees with hanging moss.

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

Heated Pool • Sleeps 25 • Pickle/Bball • Theater
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Great spot to have for a team playing in IMG events."
United States
Adam D.
The price is ￥41,184
￥145,703 total
includes taxes & fees
Oct 13 - Oct 14
Heated Pool • Sleeps 25 • Pickle/Bball • Theater
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

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

SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
Sarasota
9.4 out of 10, Exceptional, (51 reviews)
"The condo is beautifully furnished and equipped with everything we needed. It was very comfortable and we would definitely stay there again."
United States
Sharon M.
The price is ￥22,752
￥78,403 total
includes taxes & fees
Oct 10 - Oct 11
SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
Property grounds

10. 3-bedroom villa in enchanting St. Petersburg with AC comfort

3-bedroom villa in enchanting St. Petersburg with AC comfort
Childs Park
The price is ￥28,061
￥73,671 total
includes taxes & fees
Oct 15 - Oct 16
3-bedroom villa in enchanting St. Petersburg with AC comfort
A residential house with a fenced front yard, a parked car, and a palm tree.

11. Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
South Village
9.6 out of 10, Exceptional, (63 reviews)
"Close to everything, beautiful beach, clean property, pictures and description very accurate. Can’t wait to come back!"
United States
Karyn C.
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

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

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota
9.6 out of 10, Exceptional, (53 reviews)
"We loved staying here!! Having the garage was a really great bonus especially if you're going to the beach a lot! Pool was super nice and very close so that was great too! I really liked all the beach towels provided as well! Really great and nice place!"
United States
Misty S.
The price is ￥25,596
￥82,880 total
includes taxes & fees
Oct 9 - Oct 10
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
A swimming pool with a clear view of the ocean, surrounded by palm trees and a white fence.

13. Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio
Sarasota
10.0 out of 10, Exceptional, (21 reviews)
"Nice place and location. I would love to stay again."
United States
Jason M.
The price is ￥35,591
￥73,728 total
includes taxes & fees
Oct 9 - Oct 10
Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio
A balcony with wicker furniture and a view of the ocean at sunset.

14. OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear

OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear
Madeira Beach
9.8 out of 10, Exceptional, (14 reviews)
"We had a great time and the house was very comfortable and clean and we loved being right on the beach"
United States
Ann N.
The price is ￥54,510
￥90,392 total
includes taxes & fees
Nov 8 - Nov 9
OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear
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

Beachside Bliss | Rooftop Gulf Views & Fun Vibes
Madeira Beach
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely fabulous!! Great location, extremely responsive and friendly hosts, and beautiful home. It was so convenient to have laundry detergent and dish soap readily available as well as plenty of garbage bags. The rooftop was beautiful and the walk to beach can't be beat. "
United States
Dr Rachael M.
The price is ￥47,282
￥158,816 total
includes taxes & fees
Nov 4 - Nov 5
Beachside Bliss | Rooftop Gulf Views & Fun Vibes
A poolside area with a fire pit, outdoor seating, and string lights.

16. Sleeps 24-Beachfront Resort-Outdoor Pool 7BR

Sleeps 24-Beachfront Resort-Outdoor Pool 7BR
Madeira Beach
9.0 out of 10, Wonderful, (2 reviews)
"Great stay and location."
United States
Erick A.
The price is ￥97,328
￥245,169 total
includes taxes & fees
Oct 12 - Oct 13
Sleeps 24-Beachfront Resort-Outdoor Pool 7BR
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

10/10 Excellent
"Excellent palce but super pricey... it has hidden fees according the staff city fees of $150 i think is to much ..."
Julio 2-night trip
Posted 13 hours ago
Seaside at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Villas information

Number of reviews
300
Accommodation
30 Villas
Lowest Price
￥38,216
Highest Price
￥245,169

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 9.8. 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 ￥38,216 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.

Explore a world of travel with Expedia