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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Anna Maria Island villas

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

1. Beachfront · Heated Pool · King Bed

Beachfront · Heated Pool · King Bed
Holmes Beach
The price is ￥53,764
￥103,169 total
includes taxes & fees
Oct 28 - Oct 29
Beachfront · Heated Pool · King Bed
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 ￥15,280
￥37,314 total
includes taxes & fees
Oct 5 - Oct 6
Lakefront 2BR Bradenton Rental Near IMG & Beaches
A resort with a swimming pool, a covered patio, and a view of the ocean.

3. 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 ￥20,244
￥45,449 total
includes taxes & fees
Oct 9 - Oct 10
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.

4. 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 ￥20,244
￥45,765 total
includes taxes & fees
Oct 5 - Oct 6
Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
A serene lakeside setting with large trees and a white gazebo.

5. 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 ￥20,244
￥45,449 total
includes taxes & fees
Oct 6 - Oct 7
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

6. 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 ￥22,730
￥78,801 total
includes taxes & fees
Oct 5 - Oct 6
SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
A bicycle parked outside a building with a 'Hello' mat at the entrance.

7. [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 ￥11,869
￥40,921 total
includes taxes & fees
Oct 8 - Oct 9
[Beach Elements] pool view withprivate beach access
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 ￥43,567
￥148,820 total
includes taxes & fees
Oct 5 - Oct 6
Heated Pool • Sleeps 25 • Pickle/Bball • Theater
A two-story house with a swimming pool, a fenced backyard, and a front porch.

9. Downtown Gulfport Cooled Pool

Downtown Gulfport Cooled Pool
Gulfport
10.0 out of 10, Exceptional, (2 reviews)
"Nice pool"
United States
Nanci B.
Downtown Gulfport Cooled Pool
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

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 ￥23,867
￥63,345 total
includes taxes & fees
Oct 5 - Oct 6
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

11. 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 ￥25,572
￥82,329 total
includes taxes & fees
Oct 5 - Oct 6
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
A residential house with a fenced front yard, a parked car, and a palm tree.

12. 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.
The price is ￥15,627
￥47,524 total
includes taxes & fees
Oct 13 - Oct 14
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Property grounds

13. 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 ￥28,034
￥72,811 total
includes taxes & fees
Oct 15 - Oct 16
3-bedroom villa in enchanting St. Petersburg with AC comfort
A residential house with a well-maintained lawn, a pathway leading to the front door, and a small garden area with various plants.

14. Royal Blue Downtown-Gulfport-CooledPool

Royal Blue Downtown-Gulfport-CooledPool
Gulfport
10.0 out of 10, Exceptional, (5 reviews)
"Very nice private pool"
United States
Nanci B.
Royal Blue Downtown-Gulfport-CooledPool
A balcony with a white sofa and a view of the sea and buildings.

15. Luxury Beach Home N/POOL

Luxury Beach Home N/POOL
Madeira Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great location, super attentive host, and overall perfect place to stay! "
United States
Rachel K.
Luxury Beach Home N/POOL
A balcony with a table set for breakfast, including croissants, fruit, and coffee, with a city view in the background.

16. 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 ￥47,237
￥158,665 total
includes taxes & fees
Nov 3 - Nov 4
Beachside Bliss | Rooftop Gulf Views & Fun Vibes
A balcony with wicker furniture and a view of the ocean at sunset.

17. 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 ￥54,411
￥93,883 total
includes taxes & fees
Oct 18 - Oct 19
OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear
A modern single-story house with a paved driveway, a basketball hoop, and a well-maintained lawn.

18. HeatedPool • HotTub • OutdoorKitchen/Theater/Games

HeatedPool • HotTub • OutdoorKitchen/Theater/Games
South Bradenton
HeatedPool • HotTub • OutdoorKitchen/Theater/Games
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 Island Hotel Reviews

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

10/10 Excellent
"So clean and anything at all that we needed the staff was more than willing to do great experience"
MaryEllen 5-night trip
Posted less than an hour ago
Cedar Cove Resort and Cottages

Find out more about Anna Maria Island

Anna Maria Island Villas information

Number of reviews
281
Accommodation
30 Villas
Lowest Price
￥37,314
Highest Price
￥158,665

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 ￥37,314 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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