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Anna Maria Island Vacation Rentals

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1227 rentals in Anna Maria Island.
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Naut 2 Shabby Bungalow In the Heart of Anna Maria Village, vacation rental in Anna Maria Island

Naut 2 Shabby Bungalow In the Heart of Anna Maria Village

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW Luxury Canalfront Home w/Water View, Pool/Spa, Bikes, Kayaks! 25% OFF Month!, vacation 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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Great house, Amazing outdoor space! Close to Beach- Private pool/spa, vacation 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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Beach Dreams 'DreamBoat Villa', vacation rental in Anna Maria Island

Beach Dreams 'DreamBoat Villa'

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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RUNAWAY BAY #230 - 2 BED/2 BATH CONDO  - STEPS TO BRADENTON BEACH ON ANNA MARIA, vacation 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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Anna Maria The Pink Flamingo, vacation rental in Anna Maria Island

Anna Maria The Pink Flamingo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gulf Beach Place - Just a few steps from the Beach, vacation rental in Anna Maria Island

Gulf Beach Place - Just a few steps from the Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!, vacation rental in Anna Maria Island

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba, vacation 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, vacation 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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MUST...BUILD...SANDCASTLES!...... Tons of room in these 2 bedroom suites at Bali, vacation 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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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl, vacation 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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Sunrise Serenity - Spacious 3/2.5 town home with community heated pool, vacation 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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Ohana Hale Beachside  Suite D 2 Bedroom with Gulf View, vacation 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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Sunflower condo with two pools - one is directly on the beach! Elevator, vacation 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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Bermuda Bay Townhome(19) miles of white sand beach, vacation 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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Tip of the Island! 3BR, Heated Pool, Canal/Dock, Walk to Beaches & Dining, vacation rental in Anna Maria Island

Tip of the Island! 3BR, Heated Pool, Canal/Dock, Walk to Beaches & Dining

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Songbird Cottage The night full of tranquility on a quiet block., vacation rental in Anna Maria Island

Songbird Cottage The night full of tranquility on a quiet block.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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On the Beach Paradise d, vacation rental in Anna Maria Island

On the Beach Paradise d

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!, vacation rental in Anna Maria Island

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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'Living in Paradise' at 380 Aruba Circle #403 New Penthouse Condo great views, vacation 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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Island House - Funboard, vacation rental in Anna Maria Island

Island House - Funboard

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Blue Bayou, vacation rental in Anna Maria Island

Blue Bayou

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Villas #2 or #4 are cozy couple's getaway’s for vacations close to the beach, vacation rental in Anna Maria Island

The Villas #2 or #4 are cozy couple's getaway’s for vacations close to the beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 3 bed/2 bath Condo with an amazing view of the Gulf of Mexico with a p, vacation rental in Anna Maria Island

Beautiful 3 bed/2 bath Condo with an amazing view of the Gulf of Mexico with a p

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lime Kiss A! 3 Bedroom, 2 Bathroom Home Just Across The Street From The Beach, vacation 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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1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo, vacation 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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HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!, vacation 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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'Sea Gem' Beautifully remodeled Steps to beach & our bay fishing dock Mint CLEAN, vacation 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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Sandcastle - Spacious home with amazing private pool - only minutes to beach!, vacation rental in Anna Maria Island

Sandcastle - Spacious home with amazing private pool - only minutes to beach!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New, fun, close to the beach! Great Villa at the Islands West Resort!, vacation 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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Mintfish, beautiful views across Bimini Bay! 4-Bed, vacation 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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Anna Maria Beach Condo 1/1, vacation rental in Anna Maria Island

Anna Maria Beach Condo 1/1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BAY FRONT HOUSE WITH PRIVATE DOCK, vacation rental in Anna Maria Island

BAY FRONT HOUSE WITH PRIVATE DOCK

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Seaside Bungalow - Beautiful Gulf of Mexico beach and heated pool, vacation 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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Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly, vacation rental in Anna Maria Island

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

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

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beach Dreams ' Sweet Dreams Villa', vacation rental in Anna Maria Island

Beach Dreams ' Sweet Dreams Villa'

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Unobstructed Gulf view, steps to beach! Walk to popular Bridge Street Condo #4, vacation 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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Short walk to Gulf Beaches and sunrise views!!, vacation rental in Anna Maria Island

Short walk to Gulf Beaches and sunrise views!!

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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AMI Island Living -Walk to Beach-Ground Level Unit, vacation rental in Anna Maria Island

AMI Island Living -Walk to Beach-Ground Level Unit

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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PLAYA ESMERALDA/INNATTHEBEACH SUITES #1, vacation rental in Anna Maria Island

PLAYA ESMERALDA/INNATTHEBEACH SUITES #1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Beach Cottage with Heated Pool  Close to Beach, vacation 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!, vacation 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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ALMOST BEACH APARTMENT  Just Steps from the Beach -Openings Now!, vacation rental in Anna Maria Island

ALMOST BEACH APARTMENT Just Steps from the Beach -Openings Now!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Poolside Ocean View Beach Front Apartment, vacation rental in Anna Maria Island

Poolside Ocean View Beach Front Apartment

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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ONE SHELL COVE - BEACHFRONT- Steps to the sand, vacation rental in Anna Maria Island

ONE SHELL COVE - BEACHFRONT- Steps to the sand

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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ISLAND TOWNHOUSE - 200 Steps to the BEACH, vacation rental in Anna Maria Island

ISLAND TOWNHOUSE - 200 Steps to the BEACH

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Plumfish, located on the Hammock Bayou. Beautiful!, vacation rental in Anna Maria Island

Plumfish, located on the Hammock Bayou. Beautiful!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Club at AMI #10: 3 BR / 2 BA Resort on Anna Maria by RVA, Sleeps 8, vacation rental in Anna Maria Island

Beach Club at AMI #10: 3 BR / 2 BA Resort on Anna Maria by RVA, Sleeps 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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