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Holiday Homes in Anna Maria

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257 rentals in Anna Maria.
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Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!, holiday rental in Anna Maria

Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria, holiday rental in Anna Maria

Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House, holiday rental in Anna Maria

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Dragonfly - Southern charm on the North end of Anna Maria Island, holiday rental in Anna Maria

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

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl, holiday 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
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, holiday 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
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool, holiday 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
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Anna Maria, Prive Heated Pool, Lanai, holiday rental in Anna Maria

Anna Maria, Prive Heated Pool, Lanai

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Island Beach Escape, holiday rental in Anna Maria

North Island Beach Escape

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n, holiday rental in Anna Maria

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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$200  towards a private fishing charter with Captain Josh with 2020 reservation, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalow On The Bayou  (Best Location on the Island), holiday rental in Anna Maria

Bungalow On The Bayou (Best Location on the Island)

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Anna Maria Island Rentals - Beach Front - 'Angels Envy', holiday rental in Anna Maria

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, holiday 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
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MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, holiday 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
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Tucked Away in Anna Maria, holiday rental in Anna Maria

Tucked Away in Anna Maria

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gulf front, charming home right on the beach - stunning views & dogs welcome!, holiday rental in Anna Maria

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island, holiday 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
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Grab your swimsuit!! Private heated pool is now open!!!, holiday rental in Anna Maria

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine, holiday 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
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise, holiday rental in Anna Maria

Beach, Private Fishing dock, Heated Pool, Tropical Paradise

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottage with heated pool, tropical landscaping in prime location!, holiday rental in Anna Maria

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach, holiday 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
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Jan, Feb, 1 month minimum, Contact for special rates $4K mo,  $7500. 2 mo + tax, holiday 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
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Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St., holiday 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
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Charming cottage located close to beach - private heated pool, holiday rental in Anna Maria

Charming cottage located close to beach - private heated pool

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier, holiday 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
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Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!, holiday rental in Anna Maria

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

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!, holiday rental in Anna Maria

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach, holiday 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
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*Fall Specials* New Luxury-Prof. Decorated Pool/Spa 5 Minutes walk to beach, holiday rental in Anna Maria

*Fall Specials* New Luxury-Prof. Decorated Pool/Spa 5 Minutes walk to beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury, holiday 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
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Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi, holiday 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
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Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave!  Steps to Beach and Pier!, holiday 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
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NEW Luxury Canalfront Home w/Water View, Pool/Spa, Bikes, Kayaks! 25% OFF Month!, holiday 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
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Family freindly adorable cottage steps to the beach, free trolly on island, holiday rental in Anna Maria

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious 5 bedroom, canal front luxury home with private Pool and Spa!, holiday rental in Anna Maria

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

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful, well-maintained home w/ heated private pool - walk to beach, dining, holiday rental in Anna Maria

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shirley's Way Beach House - Panoramic Gulf-Front Home on Anna Maria Island, holiday 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
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Breathtaking Views and Lasting Memories - Beachfront Fun & Relaxation, holiday rental in Anna Maria

Breathtaking Views and Lasting Memories - Beachfront Fun & Relaxation

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Hear The Surf/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd/4Ba, holiday 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
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Gorgeous views,spectacular home!, holiday rental in Anna Maria

Gorgeous views,spectacular home!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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High-end home w/heated private pool & spa, courtyard, & floor-to-ceiling windows, holiday rental in Anna Maria

High-end home w/heated private pool & spa, courtyard, & floor-to-ceiling windows

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Breezy canalfront home w/ heated pool & dock - 3 blocks to Bean Point Beach!, holiday rental in Anna Maria

Breezy canalfront home w/ heated pool & dock - 3 blocks to Bean Point Beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Canal (60 Ft) Front Anna Maria Rental House Great for Boaters, holiday rental in Anna Maria

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Water front luxury home with 7 bedrooms, Pool and Spa, views of Rod 'n Reel Pier, holiday 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
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