Anna Maria Island Vacation Rentals

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Our top choices for Anna Maria Island vacation rentals

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (329)
"Fabulous stay! Super clean!"
United States
Sarah
The price is ¥28,357
¥35,888 total
includes taxes & fees
Dec 14 - Dec 15
Pelican Post at Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (399)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is ¥26,411
¥33,425 total
includes taxes & fees
Dec 21 - Dec 22
Haley's at The Anna Maria Island Inn

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (766)
"Great stay!"
United States
Sufyan
The price is ¥42,394
¥47,906 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bridgewalk Resort

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (57)
"Everything was great!!!!"
United States
David
The price is ¥74,374
¥84,042 total
includes taxes & fees
Dec 26 - Dec 27
Seabreeze at Anna Maria Island Inn

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!
2.0 star property
Bradenton Beach
9.4 out of 10, Exceptional, (15)
"Wonderful stay ! Our family loved it ! "
United States
Daniel
Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.2 out of 10, Wonderful, (250)
"Condo was great, clean , very comfortable. Great parking. Access to the beach was awesome. Free trollie outside to go up and down the island. Would definitely stay here again. "
United States
Susan
The price is ¥14,023
¥35,743 total
includes taxes & fees
Dec 14 - Dec 15
Anna Maria Sunsets - studio

Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Bayfront Home with Amazing Water Views! Private pool! – Breakaway
Anna Maria
9.4 out of 10, Exceptional, (43)
"House was beautiful, maybe needed a more comfortable LR furniture for parents but overall must give a 10/10"
United States
BEVERLY S.
Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveler
Palm Tree Villas

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.0 out of 10, Wonderful, (232)
"Great stay"
United States
Katelyn P.
The price is ¥15,549
¥37,582 total
includes taxes & fees
Dec 18 - Dec 19
Anna Maria Sunsets - studio

Charming cottage located close to beach - Private heated pool!

Charming cottage located close to beach - Private heated pool!
Anna Maria
9.4 out of 10, Exceptional, (104)
"Great location. "
United States
Summer J.
Charming cottage located close to beach - Private heated pool!

Private Pool & Hot Tub -Close to Bridge Street

Private Pool & Hot Tub -Close to Bridge Street
Bradenton Beach
10.0 out of 10, Exceptional, (3)
"Wonderful property that is comfortably close to beach. Everything at the property was what we needed and the downstairs area was super nice. This really is a hidden gem next to cortez beach. "
United States
Angel B.
Private Pool & Hot Tub -Close to Bridge Street

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

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
3.0 star property
Anna Maria
9.6 out of 10, Exceptional, (18)
"Had fun "
United States
Otis L.
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Tradewinds Beach Resort

Tradewinds Beach Resort
2.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (384)
"Everything was awesome "
United States
John
Tradewinds Beach Resort

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
Anna Maria
9.8 out of 10, Exceptional, (126)
"We had so much fun at our stay at AMI. There were so many beautiful beach's (not crowded) and delicious restaurants. A great place to relax and watch sunrise and sunset."
United States
Fran M.
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Beachfront! 2 Masters with Beachfront Views! Pool - Games!

Beachfront! 2 Masters with Beachfront Views! Pool - Games!
Anna Maria Island
10.0 out of 10, Exceptional, (31)
"We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!"
United States
Chad S.
Beachfront! 2 Masters with Beachfront Views! Pool - Games!

Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!
Anna Maria
10.0 out of 10, Exceptional, (42)
"Amazing stay in an amazing property. The pictures can’t do the view justice, truly amazing."
United States
Kenneth S.
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!
Anna Maria
8.6 out of 10, Excellent, (36)
"We loved staying in the Big Yellow House! The location absolutely could not be beat. The house had everything we needed and we thoroughly enjoyed our stay there. Can't wait to come back!"
United States
Kirsten K.
Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Bayfront Escape with Stunning Water Views and Steps to Bean Point

Bayfront Escape with Stunning Water Views and Steps to Bean Point
Anna Maria
9.6 out of 10, Exceptional, (14)
"Loved our time there!"
United States
Thomas L.
Bayfront Escape with Stunning Water Views and Steps to Bean Point

Anna Maria Island - 2/1

Anna Maria Island - 2/1
Bradenton Beach
9.6 out of 10, Exceptional, (185)
"Great time. Great place. "
United States
Matthew L.
The price is ¥15,425
¥47,377 total
includes taxes & fees
Dec 14 - Dec 15
Anna Maria Island - 2/1

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Anna Maria
10.0 out of 10, Exceptional, (288)
"Beautiful property in the perfect location to the beach. Dan and Goose were thoughtful and easily accessible. We had a great time! Would absolutely stay here again!"
United States
Hillary D.
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
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

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