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Holiday Rentals in Anna Maria Island

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1237 rentals in Anna Maria Island.
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Gorgeous views,spectacular home!, holiday rental in Anna Maria Island

Gorgeous views,spectacular home!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House, holiday rental in Anna Maria Island

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Anna Maria The Pink Flamingo, holiday rental in Anna Maria Island

Anna Maria The Pink Flamingo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Coquina Sands, view beach from balcony, priv pool, holiday rental in Anna Maria Island

Coquina Sands, view beach from balcony, priv pool

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Great Townhouse Very Close to the Beach, Shops, and Restaurants, holiday rental in Anna Maria Island

Great Townhouse Very Close to the Beach, Shops, and Restaurants

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach Dreams 'DreamBoat Villa', holiday rental in Anna Maria Island

Beach Dreams 'DreamBoat Villa'

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise, holiday rental in Anna Maria Island

Beach, Private Fishing dock, Heated Pool, Tropical Paradise

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gulf Winds A - a completely remodeled cozy cottage - pet friendly, holiday rental in Anna Maria Island

Gulf Winds A - a completely remodeled cozy cottage - pet friendly

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Anna Maria Island, holiday rental in Anna Maria Island

Beautiful Anna Maria Island

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Palm Villa - a 3 bedroom, 3 bath home with heated pool, holiday rental in Anna Maria Island

Palm Villa - a 3 bedroom, 3 bath home with heated pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BAY FRONT HOUSE WITH PRIVATE DOCK, holiday rental in Anna Maria Island

BAY FRONT HOUSE WITH PRIVATE DOCK

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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ISLAND TOWNHOUSE - 200 Steps to the BEACH, holiday rental in Anna Maria Island

ISLAND TOWNHOUSE - 200 Steps to the BEACH

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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50 Steps to Beach�.  Hot Tub! 1bd modern cottage�, holiday rental in Anna Maria Island

50 Steps to Beach�. Hot Tub! 1bd modern cottage�

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Home at Holmes Beach is a 3/3 close to the beach, pet friendly, holiday rental in Anna Maria Island

Home at Holmes Beach is a 3/3 close to the beach, pet friendly

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Anna Maria Sunset Terrace 102, holiday rental in Anna Maria Island

Anna Maria Sunset Terrace 102

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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*Clean Beach to Bay Views!* Under100 Yards to Beach, Bay, & Parks*, holiday rental in Anna Maria Island

*Clean Beach to Bay Views!* Under100 Yards to Beach, Bay, & Parks*

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ohana Hale South   West Suite, holiday rental in Anna Maria Island

Ohana Hale South West Suite

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Casa Bliss, holiday rental in Anna Maria Island

Casa Bliss

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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FALL INTO THE SEA from the porch of these one bedroom suites at Bali Hai Beachfr, holiday rental in Anna Maria Island

FALL INTO THE SEA from the porch of these one bedroom suites at Bali Hai Beachfr

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Plumfish, located on the Hammock Bayou. Beautiful!, holiday rental in Anna Maria Island

Plumfish, located on the Hammock Bayou. Beautiful!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Aquaville A - 2/1 beauty with private pool in the heart of Anna Maria. Pets!, holiday rental in Anna Maria Island

Aquaville A - 2/1 beauty with private pool in the heart of Anna Maria. Pets!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Honeyfish, stunning views across Bimimi Bay!, holiday rental in Anna Maria Island

Honeyfish, stunning views across Bimimi Bay!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Best Little Beach House on Anna Maria Island...With a pool, holiday rental in Anna Maria Island

Best Little Beach House on Anna Maria Island...With a pool

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Suite Near The Beach, holiday rental in Anna Maria Island

Luxury Suite Near The Beach

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

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 Island

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Elevator! Luxury Home, Pool, Spa,  3 min. walk to Beach, Office and Monitor!, holiday rental in Anna Maria Island

Elevator! Luxury Home, Pool, Spa, 3 min. walk to Beach, Office and Monitor!

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba, holiday rental in Anna Maria Island

Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba

3 bedrooms
4 bathrooms
Sleeps 8
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 Island

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

2 bedrooms
2 bathrooms
Sleeps 5
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 Island

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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PRIVATE POOL, WALK TO BEACH, holiday rental in Anna Maria Island

PRIVATE POOL, WALK TO BEACH

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Fabulous One/Two Bedroom Apartments  On Anna Maria Island Special Rates 4/15-5/6, holiday rental in Anna Maria Island

Fabulous One/Two Bedroom Apartments On Anna Maria Island Special Rates 4/15-5/6

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Surfside AMI, LOADED FOR FUN! Golf Cart, Heated Pool, SUP, Kayak, Beach Gear..., holiday rental in Anna Maria Island

Surfside AMI, LOADED FOR FUN! Golf Cart, Heated Pool, SUP, Kayak, Beach Gear...

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo, holiday rental in Anna Maria Island

1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!, holiday rental in Anna Maria Island

Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n, holiday rental in Anna Maria Island

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Coquina Reef!  1 Block From Beautiful Bradenton Beach!, holiday rental in Anna Maria Island

Coquina Reef! 1 Block From Beautiful Bradenton Beach!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Anna Maria, Prive Heated Pool, Lanai, holiday rental in Anna Maria Island

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 Island

North Island Beach Escape

3 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 Island

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Anna Maria Beach Condo 1/1, holiday rental in Anna Maria Island

Anna Maria Beach Condo 1/1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach, holiday rental in Anna Maria Island

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 Island

Bungalow On The Bayou (Best Location on the Island)

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dream Lover Boat & Breakfast on Anna Maria Island, holiday rental in Anna Maria Island

Dream Lover Boat & Breakfast on Anna Maria Island

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family Fun Close to Beach, Pool Slide Spa & Elevator, holiday rental in Anna Maria Island

Family Fun Close to Beach, Pool Slide Spa & Elevator

4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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New 2019 - 90sec. to beach - all day sun - big pool - quite - clean - safe - fun, holiday rental in Anna Maria Island

New 2019 - 90sec. to beach - all day sun - big pool - quite - clean - safe - fun

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 2 bed, 2 En Suite Baths, Private Htd Pool, 0 Blocks to Beach - Just Steps, holiday rental in Anna Maria Island

Luxury 2 bed, 2 En Suite Baths, Private Htd Pool, 0 Blocks to Beach - Just Steps

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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250 Foot Steps To The Gulf Of Mexico AND a low chlorine pool!, holiday rental in Anna Maria Island

250 Foot Steps To The Gulf Of Mexico AND a low chlorine pool!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Anna Maria Island Rentals - Beach Front - 'Angels Envy', holiday rental in Anna Maria Island

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Visit  Anna Maria Island! Relax at Heliconia House, enjoy your own heated pool!, holiday rental in Anna Maria Island

Visit Anna Maria Island! Relax at Heliconia House, enjoy your own heated pool!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Anna Maria Island