- USA
- Florida
- Anna Maria Island
- Summer Rental
Anna Maria Island Summer Rentals, Cottages & Cabins
Book a Place to Stay in Anna Maria Island for Your Summer Getaway
- Sarasota
- ·
- Bradenton Beach
- 1.08 mi to center
10.0
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Private Pool -
Hot Tub -
Parking -
Pool
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Private Pool
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Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.95 mi to center
9.0
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Parking
-
Pool
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Balcony/Terrace -
View
-
Parking
-
Pool
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.18 mi to center
9.4
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Parking
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Ocean View -
Balcony/Terrace
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View
-
Parking
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Ocean View
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Balcony/Terrace
-
View
- Sarasota
- ·
- Holmes Beach
- 0.75 mi to center
10.0
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Oceanfront -
Parking
-
Pool
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Ocean View
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Oceanfront
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Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Bradenton Beach
- 0.62 mi to center
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Internet -
Child Friendly -
Bedding/Linens -
Security/Safety
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Internet
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Child Friendly
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Bedding/Linens
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Security/Safety
- Sarasota
- ·
- Bradenton Beach
- 0.97 mi to center
10.0
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Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
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Ocean View
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Holmes Beach
- 0.97 mi to center
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Parking
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Pool
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Air Conditioner -
Internet
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Parking
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Pool
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Air Conditioner
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Internet
- Sarasota
- ·
- Bradenton Beach
- 0.62 mi to center
10.0
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Oceanfront
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Parking
-
Pool
-
Ocean View
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 0.95 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
-
View
-
Parking
-
Pool
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Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.25 mi to center
10.0
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Private Pool
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Parking
-
Pool
-
Ocean View
-
Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 0.83 mi to center
10.0
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Private Pool
-
Parking
-
Pool
-
Ocean View
-
Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 1.23 mi to center
10.0
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 0.86 mi to center
10.0
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Anna Maria
- 0.15 mi to center
9.8
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Parking
-
Balcony/Terrace
-
View
-
Kitchen
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
- Sarasota
- ·
- Holmes Beach
- 0.53 mi to center
9.8
-
Private Pool
-
Parking
-
Pool
-
Ocean View
-
Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Anna Maria
- 0.29 mi to center
9.8
-
Private Pool
-
Parking
-
Pool
-
Ocean View
-
Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Bradenton Beach
- 0.89 mi to center
9.8
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Sarasota
- ·
- Bradenton Beach
- 0.49 mi to center
9.8
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.31 mi to center
9.8
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Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Bradenton Beach
- 0.49 mi to center
9.8
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.32 mi to center
9.6
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Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
- Sarasota
- ·
- Bradenton Beach
- 0.61 mi to center
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Anna Maria
- 0.29 mi to center
10.0
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.28 mi to center
9.8
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
About Anna Maria Island Summer Rental on Rent Holiday
With 6293 summer rentals in or near Anna Maria Island, choosing a suitable rental home for your upcoming summer getaway on Rent Holiday is easy. Whether you are traveling with family, friends, or in a group to Anna Maria Island or areas nearby, Rent Holiday has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.
Looking for a relaxing place to stay in Anna Maria Island for a summer vacation you do not want to forget easily? Rent Holiday summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Anna Maria Island, Rent Holiday has got you covered for your next summer holiday.
Frequently Asked Questions About Anna Maria Island Summer Rental
What are the top rated Summer Rentals in Anna Maria Island?
There are a lot of options in Anna Maria Island. If you plan on staying in the Anna Maria Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Anna Maria Island:
- Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Best Little Beach House on Anna Maria Island! With a pool & steps to the beach!
- Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
- Beautiful, Gulf-Front Home on Bean Point-Halcyon House
- Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
- 1 Block From Beautiful Bradenton Beach, Restaurants, shops, and Fishing Pier!
- AMI Sunset Beach Gulf View Retreat w/Pool + Decks + WiFi + Dog-friendly
- 2 Bedroom/2 Bath Ground Level With a Heated Pool
- Dragonfly - Southern charm on the North end of Anna Maria Island
- Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.
How many summer rentals are available around Anna Maria Island, FL?
In 2026, Rentholiday offers 6293 summer rentals in or around Anna Maria Island. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Anna Maria Island?
The average price per night for a summer rental in Anna Maria Island is $609. Check the full list of summer accommodations in Anna Maria Island.
How many summer rentals are available to book in Anna Maria Island?
There are 6293 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rentholiday.
Do any summer rentals in Anna Maria Island have a private pool?
Yes, here are some popular summer holiday rentals in Anna Maria Island that have a private or indoor pool:
- Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach
- Tina's Piece of Paradise
- Tiny Tides: Adorable Cozy House!
- Fall Price Specials ~ Beachfront Paradise 110 ~ Yes, That'S Your View! ~
Check all holiday rentals with a pool in Anna Maria Island on Rentholiday.
