Anna Maria Island Vacation Rentals

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Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Anna Maria Island

Exterior
Pelican Post at Anna Maria Island Inn
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (312)
"great place overall"
United States
James
$216 nightly
The price is $244
Nov 5 - Nov 6
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Exterior
Seabreeze at Anna Maria Island Inn
Seabreeze at Anna Maria Island Inn
3.0 star property
8.8 out of 10, Excellent, (47)
"The front desk was fantastic to work with. The view was breath taking "
United States
Wendy
$292 nightly
The price is $330
Oct 30 - Oct 31
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Outdoor pool, pool umbrellas, sun loungers
Bridgewalk Resort
Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (758)
"Great stay!"
United States
Sufyan
$264 nightly
The price is $299
Nov 16 - Nov 17
Total with taxes and fees
Bridgewalk Resort
Beach nearby, white sand, sun loungers, beach towels
Haley's at The Anna Maria Island Inn
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (382)
"The staff members were so nice and super helpful!! Place was so cute! "
United States
Whitley
$197 nightly
The price is $223
Oct 30 - Oct 31
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Private beach nearby, sun loungers, beach towels
Tradewinds Beach Resort
Tradewinds Beach Resort
2.5 star property
9.2 out of 10, Wonderful, (383)
"Very cute place and easy to walk to beach "
United States
Dennison
Tradewinds Beach Resort
Terrace/patio
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
9.4 out of 10, Exceptional, (43)
"Great location, great people, awsome hosts, very prompt and caring. "
United States
Alban K.
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
A heated pool
Private Pool & Hot Tub - House close to Beach & Bridge Street
Private Pool & Hot Tub - House close to Beach & Bridge Street
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 - House close to Beach & Bridge Street
On the beach
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
9.6 out of 10, Exceptional, (15)
"The location and amenities are amazing. Would definitely stay here again."
United States
Nathan B.
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
On the beach
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
9.8 out of 10, Exceptional, (122)
"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
Property grounds
Anna Maria Sunsets - studio
Anna Maria Sunsets - studio
9.0 out of 10, Wonderful, (223)
"Great stay"
United States
Katelyn P.
$216 nightly
The price is $241
Nov 2 - Nov 3
Total with taxes and fees
Anna Maria Sunsets - studio
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
9.8 out of 10, Exceptional, (68)
"Perfect home for a family getaway "
United States
Michael M.
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
A heated pool
Beachfront Home | Pool + Spa | Games | Ocean Views
Beachfront Home | Pool + Spa | Games | Ocean Views
10.0 out of 10, Exceptional, (38)
"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"
United States
Jessica W.
Beachfront Home | Pool + Spa | Games | Ocean Views
Sun loungers, beach towels
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
10.0 out of 10, Exceptional, (2)
"What a beautiful home! Location was perfect, linens towels, decoration was on point! My husband had a blast with the putting green. Loved it!"
United States
Lis W.
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
Beach nearby, white sand, beach umbrellas, beach towels
Palm Tree Villas
Palm Tree Villas
3.0 star property
9.2 out of 10, Wonderful, (172)
"It was just a beautiful stay and love to come back next year!!"
United States
Allison
$330 nightly
The price is $353
Nov 2 - Nov 3
Total with taxes and fees
Palm Tree Villas
Microwave, stovetop, dishwasher, coffee/tea maker
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
2.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful stay ! Our family loved it ! "
United States
Daniel
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
On the beach, sun loungers, beach towels
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
10.0 out of 10, Exceptional, (96)
"great condo and great location"
United States
Kegan N.
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
Exterior
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
9.2 out of 10, Wonderful, (24)
"This was the perfect house for our family vacation! It was extremely clean and a very short walk to the beach!"
United States
Sarah P.
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
Sun loungers, beach towels
Anna Maria Sunsets - studio
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, (240)
"Cozy"
United States
David
$193 nightly
The price is $215
Nov 4 - Nov 5
Total with taxes and fees
Anna Maria Sunsets - studio
Outdoor dining
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
10.0 out of 10, Exceptional, (184)
"The bungalow is cute and cozy and had everything we needed."
United States
Laurie B.
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Fridge, microwave, oven, stovetop
Tropical Paradise On The Beach Permit VRC17-000168
Tropical Paradise On The Beach Permit VRC17-000168
9.2 out of 10, Wonderful, (143)
"The property was just as advertised, and the location can’t be beat! Will definitely stay again! "
United States
Corrie L.
Tropical Paradise On The Beach Permit VRC17-000168
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

Bridgewalk Resort

Bridgewalk Resort

10/10 Excellent
"Every aspect of the unit was well thought out."
Judy 2-night trip
Posted 17 hours ago
Bridgewalk Resort

Find out more about Anna Maria Island

Everything you need to know about Anna Maria Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Anna Maria Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $223 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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