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Holiday Homes in Anna Maria

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345 rentals in Anna Maria.
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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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Beach block/4 Bed 4.5 Bath/Private Heated Pool/Spa/Cabana/SUP/Kayaks/Bicycles, holiday rental in Anna Maria

Beach block/4 Bed 4.5 Bath/Private Heated Pool/Spa/Cabana/SUP/Kayaks/Bicycles

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful AMIBeachClub north end elevated pool home. Minutes walk to the Gulf., holiday rental in Anna Maria

Beautiful AMIBeachClub north end elevated pool home. Minutes walk to the Gulf.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Naut 2 Shabby Bungalow In the Heart of Anna Maria Village, holiday rental in Anna Maria

Naut 2 Shabby Bungalow In the Heart of Anna Maria Village

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!, holiday 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
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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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Comfortable pet-friendly duplex, two block from the Gulf and near trolly stop, holiday rental in Anna Maria

Comfortable pet-friendly duplex, two block from the Gulf and near trolly stop

4 bedrooms
4 bathrooms
Sleeps 8
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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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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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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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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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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$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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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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Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool., holiday 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
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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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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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Charming house with private heated pool, patio, and grill - steps from beach, holiday 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
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Bay Breeze Cottages #1 (The Mahi-Mahi), holiday rental in Anna Maria

Bay Breeze Cottages #1 (The Mahi-Mahi)

1 bedroom
1 bathroom
Sleeps 4
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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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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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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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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Bay Breeze Cottages #3, holiday rental in Anna Maria

Bay Breeze Cottages #3

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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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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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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Stunning luxury beachfront house with pool and spa, holiday rental in Anna Maria

Stunning luxury beachfront house with pool and spa

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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Luxury canal-front home w/ stunning heated pool - minutes to beach & Pine Avenue, holiday rental in Anna Maria

Luxury canal-front home w/ stunning heated pool - minutes to beach & Pine Avenue

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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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
More info
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Don't miss this elegant beachfront home, gorgeous views and private pool! Love t, holiday rental in Anna Maria

Don't miss this elegant beachfront home, gorgeous views and private pool! Love t

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
More info
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North End of AMI- Ground Level Family Friendly updated home, holiday rental in Anna Maria

North End of AMI- Ground Level Family Friendly updated home

3 bedrooms
2 bathrooms
Sleeps 6
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
More info
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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
More info
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Bay Breeze Cottages #2, holiday rental in Anna Maria

Bay Breeze Cottages #2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Blue Heron Cottage - Anna Maria Island, holiday rental in Anna Maria

Blue Heron Cottage - Anna Maria Island

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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