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Anna Maria Island Villas

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1185 rentals in Anna Maria Island.
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This is the one! 9 bd, Waterslide, Pool, Spa, Rooftop Deck - Island Sol!, holiday rental in Anna Maria Island

This is the one! 9 bd, Waterslide, Pool, Spa, Rooftop Deck - Island Sol!

9 bedrooms
7 bathrooms
Sleeps 22
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 Island

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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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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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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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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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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Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453, holiday rental in Anna Maria Island

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach Haven #204 of Holmes Beach FL, holiday rental in Anna Maria Island

Beach Haven #204 of Holmes Beach FL

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Roof Top deck plus outside bar and 1 min to the beach!, holiday rental in Anna Maria Island

Roof Top deck plus outside bar and 1 min to the beach!

6 bedrooms
5 bathrooms
Sleeps 12
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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Sunrise Serenity - Spacious 3/2.5 town home with community heated pool, holiday rental in Anna Maria Island

Sunrise Serenity - Spacious 3/2.5 town home with community heated pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bermuda Bay Townhome(19) miles of white sand beach, holiday rental in Anna Maria Island

Bermuda Bay Townhome(19) miles of white sand beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunflower condo with two pools - one is directly on the beach! Elevator, holiday rental in Anna Maria Island

Sunflower condo with two pools - one is directly on the beach! Elevator

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RUNAWAY BAY #230 - 2 BED/2 BATH CONDO  - STEPS TO BRADENTON BEACH ON ANNA MARIA, holiday rental in Anna Maria Island

RUNAWAY BAY #230 - 2 BED/2 BATH CONDO - STEPS TO BRADENTON BEACH ON ANNA MARIA

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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8 bd luxury home with private pool + spa! Close to the beach, great location!, holiday rental in Anna Maria Island

8 bd luxury home with private pool + spa! Close to the beach, great location!

8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Blue Bayou, holiday rental in Anna Maria Island

Blue Bayou

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Living in Paradise' at 380 Aruba Circle #403 New Penthouse Condo great views, holiday rental in Anna Maria Island

'Living in Paradise' at 380 Aruba Circle #403 New Penthouse Condo great views

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!, holiday rental in Anna Maria Island

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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HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!, holiday rental in Anna Maria Island

HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!

4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Lime Kiss A! 3 Bedroom, 2 Bathroom Home Just Across The Street From The Beach, holiday rental in Anna Maria Island

Lime Kiss A! 3 Bedroom, 2 Bathroom Home Just Across The Street From The Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Island House - Funboard, holiday rental in Anna Maria Island

Island House - Funboard

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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'Sea Gem' Beautifully remodeled Steps to beach & our bay fishing dock Mint CLEAN, holiday rental in Anna Maria Island

'Sea Gem' Beautifully remodeled Steps to beach & our bay fishing dock Mint CLEAN

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly built home w/ heated private pool only a few blocks away from Gulf beaches, holiday rental in Anna Maria Island

Newly built home w/ heated private pool only a few blocks away from Gulf beaches

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New, fun, close to the beach! Great Villa at the Islands West Resort!, holiday rental in Anna Maria Island

New, fun, close to the beach! Great Villa at the Islands West Resort!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ohana Hale Beachside  Suite D 2 Bedroom with Gulf View, holiday rental in Anna Maria Island

Ohana Hale Beachside Suite D 2 Bedroom with Gulf View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Angie's Place! 2br/2ba, heated pool and a view of the Gulf!, holiday rental in Anna Maria Island

Angie's Place! 2br/2ba, heated pool and a view of the Gulf!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mintfish, beautiful views across Bimini Bay! 4-Bed, holiday rental in Anna Maria Island

Mintfish, beautiful views across Bimini Bay! 4-Bed

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Seaside Bungalow - Beautiful Gulf of Mexico beach and heated pool, holiday rental in Anna Maria Island

Seaside Bungalow - Beautiful Gulf of Mexico beach and heated pool

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Unobstructed Gulf view, steps to beach! Walk to popular Bridge Street Condo #4, holiday rental in Anna Maria Island

Unobstructed Gulf view, steps to beach! Walk to popular Bridge Street Condo #4

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home w/ Dock, Pool, Kayaks: Walk to Palma Sola Bay, holiday rental in Anna Maria Island

Home w/ Dock, Pool, Kayaks: Walk to Palma Sola Bay

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Dreams ' Sweet Dreams Villa', holiday rental in Anna Maria Island

Beach Dreams ' Sweet Dreams Villa'

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Great house, Amazing outdoor space! Close to Beach- Private pool/spa, holiday rental in Anna Maria Island

Great house, Amazing outdoor space! Close to Beach- Private pool/spa

5 bedrooms
4 bathrooms
Sleeps 10
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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Modern Beach Cottage with Heated Pool  Close to Beach, holiday rental in Anna Maria Island

Modern Beach Cottage with Heated Pool Close to Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gulf View Cottage boasts unsurpassed views and that old Florida charm! Come see!, holiday rental in Anna Maria Island

Gulf View Cottage boasts unsurpassed views and that old Florida charm! Come see!

2 bedrooms
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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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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MUST...BUILD...SANDCASTLES!...... Tons of room in these 2 bedroom suites at Bali, holiday rental in Anna Maria Island

MUST...BUILD...SANDCASTLES!...... Tons of room in these 2 bedroom suites at Bali

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Poolside Ocean View Beach Front Apartment, holiday rental in Anna Maria Island

Poolside Ocean View Beach Front Apartment

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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PLAYA ESMERALDA/INNATTHEBEACH SUITES #1, holiday rental in Anna Maria Island

PLAYA ESMERALDA/INNATTHEBEACH SUITES #1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gulf view condo w/ WiFi, AC, full kitchen, furnished balcony, & more!, holiday rental in Anna Maria Island

Gulf view condo w/ WiFi, AC, full kitchen, furnished balcony, & more!

1 bedroom
1 bathroom
Sleeps 4
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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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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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 6
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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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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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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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 12
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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