We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Anna Maria Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
268 rentals in Anna Maria.
Sort by:
Tripadvisor Sort
NEW Luxury Canalfront Home w/Water View, Pool/Spa, Bikes, Kayaks! 25% OFF Month!, vacation rental in Anna Maria

NEW Luxury Canalfront Home w/Water View, Pool/Spa, Bikes, Kayaks! 25% OFF Month!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Naut 2 Shabby Bungalow In the Heart of Anna Maria Village, vacation rental in Anna Maria

Naut 2 Shabby Bungalow In the Heart of Anna Maria Village

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!, vacation rental in Anna Maria

Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl, vacation rental in Anna Maria

Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly, vacation rental in Anna Maria

Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Beautiful, Gulf-Front Home on Bean Point--Halcyon House, vacation rental in Anna Maria

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria

Dragonfly - Southern charm on the North end of Anna Maria Island

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria

Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n, vacation rental in Anna Maria

Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool, vacation rental in Anna Maria

Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Anna Maria rentals sent straight to your email!
North Island Beach Escape, vacation rental in Anna Maria

North Island Beach Escape

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Anna Maria, Prive Heated Pool, Lanai, vacation rental in Anna Maria

Anna Maria, Prive Heated Pool, Lanai

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach, vacation rental in Anna Maria

Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
$200  towards a private fishing charter with Captain Josh with 2020 reservation, vacation rental in Anna Maria

$200 towards a private fishing charter with Captain Josh with 2020 reservation

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Bungalow On The Bayou  (Best Location on the Island), vacation rental in Anna Maria

Bungalow On The Bayou (Best Location on the Island)

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Anna Maria Island Rentals - Beach Front - 'Angels Envy', vacation rental in Anna Maria

Anna Maria Island Rentals - Beach Front - 'Angels Envy'

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park, vacation rental in Anna Maria

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Gulf front, charming home right on the beach - stunning views & dogs welcome!, vacation rental in Anna Maria

Gulf front, charming home right on the beach - stunning views & dogs welcome!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, vacation rental in Anna Maria

MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool., vacation rental in Anna Maria

Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool.

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tucked Away in Anna Maria, vacation rental in Anna Maria

Tucked Away in Anna Maria

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, vacation rental in Anna Maria

North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming house with private heated pool, patio, and grill - steps from beach, vacation rental in Anna Maria

Charming house with private heated pool, patio, and grill - steps from beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!, vacation rental in Anna Maria

Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming cottage with heated pool, tropical landscaping in prime location!, vacation rental in Anna Maria

Charming cottage with heated pool, tropical landscaping in prime location!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location, vacation rental in Anna Maria

Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine, vacation rental in Anna Maria

Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island, vacation rental in Anna Maria

Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming cottage located close to beach - private heated pool, vacation rental in Anna Maria

Charming cottage located close to beach - private heated pool

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beach, Private Fishing dock, Heated Pool, Tropical Paradise, vacation rental in Anna Maria

Beach, Private Fishing dock, Heated Pool, Tropical Paradise

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Jan, Feb, 1 month minimum, Contact for special rates $4K mo,  $7500. 2 mo + tax, vacation rental in Anna Maria

Jan, Feb, 1 month minimum, Contact for special rates $4K mo, $7500. 2 mo + tax

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Grab your swimsuit!! Private heated pool is now open!!!, vacation rental in Anna Maria

Grab your swimsuit!! Private heated pool is now open!!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach, vacation rental in Anna Maria

Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach, vacation rental in Anna Maria

Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi, vacation rental in Anna Maria

Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave!  Steps to Beach and Pier!, vacation rental in Anna Maria

Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier, vacation rental in Anna Maria

Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St., vacation rental in Anna Maria

Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Family freindly adorable cottage steps to the beach, free trolly on island, vacation rental in Anna Maria

Family freindly adorable cottage steps to the beach, free trolly on island

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!, vacation rental in Anna Maria

Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!, vacation rental in Anna Maria

Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury, vacation rental in Anna Maria

Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Canal (60 Ft) Front Anna Maria Rental House Great for Boaters, vacation rental in Anna Maria

Canal (60 Ft) Front Anna Maria Rental House Great for Boaters

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Gorgeous views,spectacular home!, vacation rental in Anna Maria

Gorgeous views,spectacular home!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
Shirley's Way Beach House - Panoramic Gulf-Front Home on Anna Maria Island, vacation rental in Anna Maria

Shirley's Way Beach House - Panoramic Gulf-Front Home on Anna Maria Island

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Water front luxury home with 7 bedrooms, Pool and Spa, views of Rod 'n Reel Pier, vacation rental in Anna Maria

Water front luxury home with 7 bedrooms, Pool and Spa, views of Rod 'n Reel Pier

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spacious 5 bedroom, canal front luxury home with private Pool and Spa!, vacation rental in Anna Maria

Spacious 5 bedroom, canal front luxury home with private Pool and Spa!

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful, well-maintained home w/ heated private pool - walk to beach, dining, vacation rental in Anna Maria

Beautiful, well-maintained home w/ heated private pool - walk to beach, dining

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Hear The Surf/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd/4Ba, vacation rental in Anna Maria

Hear The Surf/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd/4Ba

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Vibrant Beach House – Heated Private Pool and Steps to the Beach, vacation rental in Anna Maria

Vibrant Beach House – Heated Private Pool and Steps to the Beach

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Previous
Frequently Asked Questions about Anna Maria