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Anna Maria Island Villas

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2243 rentals in Anna Maria Island.
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 Songbird Cottage, holiday rental in Anna Maria Island
 Songbird Cottage, holiday rental in Anna Maria Island
 Songbird Cottage, holiday rental in Anna Maria Island

Songbird Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard, holiday rental in Anna Maria Island
Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard, holiday rental in Anna Maria Island
Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard, holiday rental in Anna Maria Island

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Island House - Funboard, holiday rental in Anna Maria Island
Island House - Funboard, holiday rental in Anna Maria Island
Island House - Funboard, holiday rental in Anna Maria Island

Island House - Funboard

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean View Villa, holiday rental in Anna Maria Island
Ocean View Villa, holiday rental in Anna Maria Island
Ocean View Villa, holiday rental in Anna Maria Island

Ocean View Villa

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches, holiday rental in Anna Maria Island
Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches, holiday rental in Anna Maria Island
Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches, holiday rental in Anna Maria Island

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Best Little Beach House on Anna Maria Island...With a pool

Holiday Rental House
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, holiday rental in Anna Maria Island
Beautiful, Gulf-Front Home on Bean Point--Halcyon House, holiday rental in Anna Maria Island

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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, holiday rental in Anna Maria Island
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Luxury Suite Near The Beach, holiday rental in Anna Maria Island
Luxury Suite Near The Beach, holiday rental in Anna Maria Island
Luxury Suite Near The Beach, holiday rental in Anna Maria Island

Luxury Suite Near The Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Elevator! Luxury Home, Pool, Spa, 3 min. walk to Beach, Office and Monitor!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
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Blue Sky:  Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!, holiday rental in Anna Maria Island
Blue Sky:  Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!, holiday rental in Anna Maria Island
Blue Sky:  Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!, holiday rental in Anna Maria Island

Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Seaside Sanctuary #1 - World's Greatest Sunsets!, holiday rental in Anna Maria Island
Seaside Sanctuary #1 - World's Greatest Sunsets!, holiday rental in Anna Maria Island
Seaside Sanctuary #1 - World's Greatest Sunsets!, holiday rental in Anna Maria Island

Seaside Sanctuary #1 - World's Greatest Sunsets!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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, holiday rental in Anna Maria Island
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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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!, holiday rental in Anna Maria Island
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!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Spectacular Beachfront House with Pool, holiday rental in Anna Maria Island
Spectacular Beachfront House with Pool, holiday rental in Anna Maria Island
Spectacular Beachfront House with Pool, holiday rental in Anna Maria Island

Spectacular Beachfront House with Pool

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock, holiday rental in Anna Maria Island
INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock, holiday rental in Anna Maria Island
INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock, holiday rental in Anna Maria Island

INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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PRIVATE POOL, WALK TO BEACH, holiday rental in Anna Maria Island
PRIVATE POOL, WALK TO BEACH, holiday rental in Anna Maria Island
PRIVATE POOL, WALK TO BEACH, holiday rental in Anna Maria Island

PRIVATE POOL, WALK TO BEACH

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit, holiday rental in Anna Maria Island
Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit, holiday rental in Anna Maria Island
Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit, holiday rental in Anna Maria Island

Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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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, holiday rental in Anna Maria Island
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Serendipity - Beach Front Home on Bean Point , Anna Maria, holiday rental in Anna Maria Island
Serendipity - Beach Front Home on Bean Point , Anna Maria, holiday rental in Anna Maria Island
Serendipity - Beach Front Home on Bean Point , Anna Maria, holiday rental in Anna Maria Island

Serendipity - Beach Front Home on Bean Point , Anna Maria

Holiday Rental House
4 bedrooms
8 bathrooms
Sleeps 8
Match: Sleeps
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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!, holiday rental in Anna Maria Island
Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!, holiday rental in Anna Maria Island
Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!, holiday rental in Anna Maria Island

Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
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North Island Beach Escape, holiday rental in Anna Maria Island
North Island Beach Escape, holiday rental in Anna Maria Island
North Island Beach Escape, holiday rental in Anna Maria Island

North Island Beach Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Water Beach House:  5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach, holiday rental in Anna Maria Island
Blue Water Beach House:  5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach, holiday rental in Anna Maria Island
Blue Water Beach House:  5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach, holiday rental in Anna Maria Island

Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
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!, holiday rental in Anna Maria Island
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!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Pricing Specials!  2 BR 2 Full BA on Anna Maria Island just steps to Beach!, holiday rental in Anna Maria Island
Pricing Specials!  2 BR 2 Full BA on Anna Maria Island just steps to Beach!, holiday rental in Anna Maria Island
Pricing Specials!  2 BR 2 Full BA on Anna Maria Island just steps to Beach!, holiday rental in Anna Maria Island

Pricing Specials! 2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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, holiday rental in Anna Maria Island
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

Holiday Rental House
0 bedrooms
4 bathrooms
Sleeps 8
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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..., holiday rental in Anna Maria Island
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...

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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, holiday rental in Anna Maria Island
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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!, holiday rental in Anna Maria Island
Coquina Reef!  1 Block From Beautiful Bradenton Beach!, holiday rental in Anna Maria Island

Coquina Reef! 1 Block From Beautiful Bradenton Beach!

Condo/Apartment
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, holiday rental in Anna Maria Island
Anna Maria, Prive Heated Pool, Lanai, holiday rental in Anna Maria Island

Anna Maria, Prive Heated Pool, Lanai

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, holiday rental in Anna Maria Island
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, holiday rental in Anna Maria Island
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, holiday rental in Anna Maria Island

Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!, holiday rental in Anna Maria Island
Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!, holiday rental in Anna Maria Island
Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!, holiday rental in Anna Maria Island

Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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 Island
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, holiday rental in Anna Maria Island
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, holiday rental in Anna Maria Island

MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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, holiday rental in Anna Maria Island
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach

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

Bungalow On The Bayou (Best Location on the Island)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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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, holiday rental in Anna Maria Island
Family Fun Close to Beach, Pool Slide Spa & Elevator, holiday rental in Anna Maria Island

Family Fun Close to Beach, Pool Slide Spa & Elevator

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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Anna Maria Beach Condo 1/1, holiday rental in Anna Maria Island
Anna Maria Beach Condo 1/1, holiday rental in Anna Maria Island
Anna Maria Beach Condo 1/1, holiday rental in Anna Maria Island

Anna Maria Beach Condo 1/1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Pirate  #8, Family Friendly Cottage By The Sea on Anna Maria Island, holiday rental in Anna Maria Island
Sea Pirate  #8, Family Friendly Cottage By The Sea on Anna Maria Island, holiday rental in Anna Maria Island
Sea Pirate  #8, Family Friendly Cottage By The Sea on Anna Maria Island, holiday rental in Anna Maria Island

Sea Pirate #8, Family Friendly Cottage By The Sea on Anna Maria Island

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!, holiday rental in Anna Maria Island
Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!, holiday rental in Anna Maria Island
Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!, holiday rental in Anna Maria Island

Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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*VERY CLEAN !!!*ANNA MARIA ISLAND*2BED/2BATH*COMPLETELY UPDATED/WELL MAINTAINED*, holiday rental in Anna Maria Island
*VERY CLEAN !!!*ANNA MARIA ISLAND*2BED/2BATH*COMPLETELY UPDATED/WELL MAINTAINED*, holiday rental in Anna Maria Island
*VERY CLEAN !!!*ANNA MARIA ISLAND*2BED/2BATH*COMPLETELY UPDATED/WELL MAINTAINED*, holiday rental in Anna Maria Island

*VERY CLEAN !!!*ANNA MARIA ISLAND*2BED/2BATH*COMPLETELY UPDATED/WELL MAINTAINED*

Condo/Apartment
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 Island
$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, holiday rental in Anna Maria Island

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, holiday rental in Anna Maria Island
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, holiday rental in Anna Maria Island
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, holiday rental in Anna Maria Island

Luxury Beach Cottage for Families on the North Shore of Anna Maria Island

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, holiday rental in Anna Maria Island
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, holiday rental in Anna Maria Island
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, holiday rental in Anna Maria Island

North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Stella Marina on Anna Maria Island, holiday rental in Anna Maria Island
Stella Marina on Anna Maria Island, holiday rental in Anna Maria Island
Stella Marina on Anna Maria Island, holiday rental in Anna Maria Island

Stella Marina on Anna Maria Island

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2BR/2BA Bayfront Retreat! Watch Sunrise Over Water with Bay Views & Free WIFI, holiday rental in Anna Maria Island
2BR/2BA Bayfront Retreat! Watch Sunrise Over Water with Bay Views & Free WIFI, holiday rental in Anna Maria Island
2BR/2BA Bayfront Retreat! Watch Sunrise Over Water with Bay Views & Free WIFI, holiday rental in Anna Maria Island

2BR/2BA Bayfront Retreat! Watch Sunrise Over Water with Bay Views & Free WIFI

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Beach View Retreat - 180-degree Beach/Gulf Views, beach 30 feet away, Bridge Str, holiday rental in Anna Maria Island
Beach View Retreat - 180-degree Beach/Gulf Views, beach 30 feet away, Bridge Str, holiday rental in Anna Maria Island
Beach View Retreat - 180-degree Beach/Gulf Views, beach 30 feet away, Bridge Str, holiday rental in Anna Maria Island

Beach View Retreat - 180-degree Beach/Gulf Views, beach 30 feet away, Bridge Str

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious canal front home with private heated pool on Anna Maria Island, holiday rental in Anna Maria Island
Spacious canal front home with private heated pool on Anna Maria Island, holiday rental in Anna Maria Island
Spacious canal front home with private heated pool on Anna Maria Island, holiday rental in Anna Maria Island

Spacious canal front home with private heated pool on Anna Maria Island

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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!, holiday rental in Anna Maria Island
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!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Anna Maria Island