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Anna Maria Vacation Rentals

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788 rentals in Anna Maria.
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Gorgeous views,spectacular home!, vacation rental in Anna Maria
Gorgeous views,spectacular home!, vacation rental in Anna Maria
Gorgeous views,spectacular home!, vacation rental in Anna Maria

Gorgeous views,spectacular home!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Seaside Sanctuary #1 - World's Greatest Sunsets!, vacation rental in Anna Maria
Seaside Sanctuary #1 - World's Greatest Sunsets!, vacation rental in Anna Maria
Seaside Sanctuary #1 - World's Greatest Sunsets!, vacation rental in Anna Maria

Seaside Sanctuary #1 - World's Greatest Sunsets!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House, vacation rental in Anna Maria
Beautiful, Gulf-Front Home on Bean Point--Halcyon House, vacation rental in Anna Maria
Beautiful, Gulf-Front Home on Bean Point--Halcyon House, vacation rental in Anna Maria

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, vacation rental in Anna Maria
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, vacation rental in Anna Maria
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool, vacation rental in Anna Maria

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria
Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria
Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria

Dragonfly - Southern charm on the North end of Anna Maria Island

Rental Home
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock, vacation rental in Anna Maria
Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock, vacation rental in Anna Maria
Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock, vacation rental in Anna Maria

Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Beachfront House with Pool, vacation rental in Anna Maria
Spectacular Beachfront House with Pool, vacation rental in Anna Maria
Spectacular Beachfront House with Pool, vacation rental in Anna Maria

Spectacular Beachfront House with Pool

Rental Home
4 bedrooms
5 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
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl, vacation rental in Anna Maria
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl, vacation rental in Anna Maria

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

Rental Home
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!, vacation rental in Anna Maria
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria

Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!, vacation rental in Anna Maria
SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!, vacation rental in Anna Maria
SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!, vacation rental in Anna Maria

SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool, vacation rental in Anna Maria
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool, vacation rental in Anna Maria
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool, vacation rental in Anna Maria

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Charming house with private heated pool, lanai.  Great location to beach & shops, vacation rental in Anna Maria
Charming house with private heated pool, lanai.  Great location to beach & shops, vacation rental in Anna Maria
Charming house with private heated pool, lanai.  Great location to beach & shops, vacation rental in Anna Maria

Charming house with private heated pool, lanai. Great location to beach & shops

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Island Beach Escape, vacation rental in Anna Maria
North Island Beach Escape, vacation rental in Anna Maria
North Island Beach Escape, vacation rental in Anna Maria

North Island Beach Escape

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Beautiful, decorated and furnished, spacious Great Room family & kid friendly,, vacation rental in Anna Maria
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,, vacation rental in Anna Maria
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,, vacation rental in Anna Maria

Beautiful, decorated and furnished, spacious Great Room family & kid friendly,

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Canal Front Home w/ Private Heated Pool on AMI, vacation rental in Anna Maria
Spacious Canal Front Home w/ Private Heated Pool on AMI, vacation rental in Anna Maria
Spacious Canal Front Home w/ Private Heated Pool on AMI, vacation rental in Anna Maria

Spacious Canal Front Home w/ Private Heated Pool on AMI

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bungalow On The Bayou  (Best Location on the Island), vacation rental in Anna Maria
Bungalow On The Bayou  (Best Location on the Island), vacation rental in Anna Maria
Bungalow On The Bayou  (Best Location on the Island), vacation rental in Anna Maria

Bungalow On The Bayou (Best Location on the Island)

Rental Home
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, vacation rental in Anna Maria
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, vacation rental in Anna Maria
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street, vacation rental in Anna Maria

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Naut 2 Shabby Bungalow  | A sweet and cozy getaway on Pine Avenue!, vacation rental in Anna Maria
Naut 2 Shabby Bungalow  | A sweet and cozy getaway on Pine Avenue!, vacation rental in Anna Maria
Naut 2 Shabby Bungalow  | A sweet and cozy getaway on Pine Avenue!, vacation rental in Anna Maria

Naut 2 Shabby Bungalow | A sweet and cozy getaway on Pine Avenue!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spoonbill Hideaway*Huge Pool/Spa/Across from Gulf Beach*10% to Hurricane Relief!, vacation rental in Anna Maria
Spoonbill Hideaway*Huge Pool/Spa/Across from Gulf Beach*10% to Hurricane Relief!, vacation rental in Anna Maria
Spoonbill Hideaway*Huge Pool/Spa/Across from Gulf Beach*10% to Hurricane Relief!, vacation rental in Anna Maria

Spoonbill Hideaway*Huge Pool/Spa/Across from Gulf Beach*10% to Hurricane Relief!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Cabana, vacation rental in Anna Maria
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Cabana, vacation rental in Anna Maria
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Cabana, vacation rental in Anna Maria

Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Cabana

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Island Living, refreshing outdoor shower and  pool ,  pet friendly if approved, vacation rental in Anna Maria
Island Living, refreshing outdoor shower and  pool ,  pet friendly if approved, vacation rental in Anna Maria
Island Living, refreshing outdoor shower and  pool ,  pet friendly if approved, vacation rental in Anna Maria

Island Living, refreshing outdoor shower and pool , pet friendly if approved

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, vacation rental in Anna Maria
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, vacation rental in Anna Maria
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator, vacation rental in Anna Maria

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, vacation rental in Anna Maria
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, vacation rental in Anna Maria
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island, vacation rental in Anna Maria

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Seaside Sanctuary #2 - Read Our Reviews - 100%  Positive, vacation rental in Anna Maria
Seaside Sanctuary #2 - Read Our Reviews - 100%  Positive, vacation rental in Anna Maria
Seaside Sanctuary #2 - Read Our Reviews - 100%  Positive, vacation rental in Anna Maria

Seaside Sanctuary #2 - Read Our Reviews - 100% Positive

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria
Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria
Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria

Charming cottage in quiet area, close to beach & bay.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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$200  towards a private fishing charter with Captain Josh with 2020 reservation, vacation rental in Anna Maria
$200  towards a private fishing charter with Captain Josh with 2020 reservation, vacation rental in Anna Maria
$200  towards a private fishing charter with Captain Josh with 2020 reservation, vacation rental in Anna Maria

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area, vacation rental in Anna Maria
Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area, vacation rental in Anna Maria
Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area, vacation rental in Anna Maria

Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria
Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria
Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria
AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria
AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria

AMI North End Private Heated Pool. Great location to beach

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Nov 26 - Dec 3, 2022 $1999/wk*- Waterfront/Beach/Hot Tub/Pool/Dock/Putting Green, vacation rental in Anna Maria
Nov 26 - Dec 3, 2022 $1999/wk*- Waterfront/Beach/Hot Tub/Pool/Dock/Putting Green, vacation rental in Anna Maria
Nov 26 - Dec 3, 2022 $1999/wk*- Waterfront/Beach/Hot Tub/Pool/Dock/Putting Green, vacation rental in Anna Maria

Nov 26 - Dec 3, 2022 $1999/wk*- Waterfront/Beach/Hot Tub/Pool/Dock/Putting Green

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED, vacation rental in Anna Maria
BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED, vacation rental in Anna Maria
BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED, vacation rental in Anna Maria

BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria
Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria
Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria

Northshore Beach House near Pine Ave, north end of Anna Maria Island

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria

ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise, vacation rental in Anna Maria
Beach, Private Fishing dock, Heated Pool, Tropical Paradise, vacation rental in Anna Maria
Beach, Private Fishing dock, Heated Pool, Tropical Paradise, vacation rental in Anna Maria

Beach, Private Fishing dock, Heated Pool, Tropical Paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach, vacation rental in Anna Maria
New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach, vacation rental in Anna Maria
New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach, vacation rental in Anna Maria

New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private heated pool with this charming bungalow!, vacation rental in Anna Maria
Private heated pool with this charming bungalow!, vacation rental in Anna Maria
Private heated pool with this charming bungalow!, vacation rental in Anna Maria

Private heated pool with this charming bungalow!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 blocks to sugar sand beach!  Large, heated pool and 20 ft dock., vacation rental in Anna Maria
3 blocks to sugar sand beach!  Large, heated pool and 20 ft dock., vacation rental in Anna Maria
3 blocks to sugar sand beach!  Large, heated pool and 20 ft dock., vacation rental in Anna Maria

3 blocks to sugar sand beach! Large, heated pool and 20 ft dock.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Anna Belle by Beach Boutique Rentals, vacation rental in Anna Maria
Anna Belle by Beach Boutique Rentals, vacation rental in Anna Maria
Anna Belle by Beach Boutique Rentals, vacation rental in Anna Maria

Anna Belle by Beach Boutique Rentals

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!, vacation rental in Anna Maria
Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!, vacation rental in Anna Maria
Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!, vacation rental in Anna Maria

Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming gulf-front home right on the beach - stunning views, dogs welcome, vacation rental in Anna Maria
Charming gulf-front home right on the beach - stunning views, dogs welcome, vacation rental in Anna Maria
Charming gulf-front home right on the beach - stunning views, dogs welcome, vacation rental in Anna Maria

Charming gulf-front home right on the beach - stunning views, dogs welcome

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Blue Heron Cottage - Anna Maria Island, vacation rental in Anna Maria
Blue Heron Cottage - Anna Maria Island, vacation rental in Anna Maria
Blue Heron Cottage - Anna Maria Island, vacation rental in Anna Maria

Blue Heron Cottage - Anna Maria Island

Rental Home
1 bedroom
3 bathrooms
Sleeps 4
Match: Sleeps
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VIEWS for days! Beautifully beachy 3 bedroom condo with a Pool, ideal location!, vacation rental in Anna Maria
VIEWS for days! Beautifully beachy 3 bedroom condo with a Pool, ideal location!, vacation rental in Anna Maria
VIEWS for days! Beautifully beachy 3 bedroom condo with a Pool, ideal location!, vacation rental in Anna Maria

VIEWS for days! Beautifully beachy 3 bedroom condo with a Pool, ideal location!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tucked Away in Anna Maria, vacation rental in Anna Maria
Tucked Away in Anna Maria, vacation rental in Anna Maria
Tucked Away in Anna Maria, vacation rental in Anna Maria

Tucked Away in Anna Maria

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria
Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria
Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria

Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool, vacation rental in Anna Maria
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool, vacation rental in Anna Maria
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool, vacation rental in Anna Maria

Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier, vacation rental in Anna Maria
Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier, vacation rental in Anna Maria
Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier, vacation rental in Anna Maria

Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Turtle Cottage - Anna Maria Island, vacation rental in Anna Maria
Turtle Cottage - Anna Maria Island, vacation rental in Anna Maria
Turtle Cottage - Anna Maria Island, vacation rental in Anna Maria

Turtle Cottage - Anna Maria Island

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Family freindly adorable cottage steps to the beach, free trolly on island, vacation rental in Anna Maria
Family freindly adorable cottage steps to the beach, free trolly on island, vacation rental in Anna Maria
Family freindly adorable cottage steps to the beach, free trolly on island, vacation rental in Anna Maria

Family freindly adorable cottage steps to the beach, free trolly on island

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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