Vacation rentals in Anna Maria Island, FL

Best vacation rentals and Airbnb offers in Anna Maria Island, FL

10 ★ 147 reviews

LOW PRICES! AMI Beach Resort Sanctuary Unit 3 Central Holmes Beach FL

Apartment, Anna Maria Island

LOW PRICES! AMI Beach Resort Sanctuary Unit 3 Central Holmes Beach FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About LOW PRICES! AMI Beach Resort Sanctuary Unit 3 Central Holmes Beach FL

LOW PRICES! AMI Beach Resort Sanctuary Unit 3 Central Holmes Beach FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,587.

From$227/night

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10 ★ 125 reviews

LOW PRICES! Serene AMI Beach Resort Unit 1 Central Holmes Beach, FL

Apartment, Anna Maria Island

LOW PRICES! Serene AMI Beach Resort Unit 1 Central Holmes Beach, FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About LOW PRICES! Serene AMI Beach Resort Unit 1 Central Holmes Beach, FL

LOW PRICES! Serene AMI Beach Resort Unit 1 Central Holmes Beach, FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,587.

From$227/night

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10 ★ 100 reviews

LOW PRICES! Tranquil AMI Beach Resort Unit 2 Central Holmes Beach, FL

Apartment, Anna Maria Island

LOW PRICES! Tranquil AMI Beach Resort Unit 2 Central Holmes Beach, FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About LOW PRICES! Tranquil AMI Beach Resort Unit 2 Central Holmes Beach, FL

LOW PRICES! Tranquil AMI Beach Resort Unit 2 Central Holmes Beach, FL is a apartment in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,587.

From$227/night

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10 ★ 61 reviews

Anna Maria 2 Family Home w/ pool, beach/3 blocks.

Holiday Home, Anna Maria Island

Anna Maria 2 Family Home w/ pool, beach/3 blocks. is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Anna Maria 2 Family Home w/ pool, beach/3 blocks.

Anna Maria 2 Family Home w/ pool, beach/3 blocks. is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,178.

From$311/night

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Waterfront vacation rentals in Anna Maria Island, FL

Discover vacation rentals close to the coast, water, and beach areas around Anna Maria Island, FL.

10 ★ 76 reviews

Relax at Bryant’s Beach Bungalow!

Holiday Home, Anna Maria Island

Relax at Bryant’s Beach Bungalow! is a holiday home in Anna Maria Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Relax at Bryant’s Beach Bungalow!

Relax at Bryant’s Beach Bungalow! is a holiday home in Anna Maria Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,826.

From$404/night

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10 ★ 8 reviews

Beach getaway pool, spa, mini golf, walk to beach

Holiday Home, Anna Maria Island

Beach getaway pool, spa, mini golf, walk to beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Beach getaway pool, spa, mini golf, walk to beach

Beach getaway pool, spa, mini golf, walk to beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,045.

From$292/night

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9.8 ★ 110 reviews

Coastal Rental Steps 2 Beach/Bridge/Tropical Crtyd

Condo, Anna Maria Island

Coastal Rental Steps 2 Beach/Bridge/Tropical Crtyd is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Coastal Rental Steps 2 Beach/Bridge/Tropical Crtyd

Coastal Rental Steps 2 Beach/Bridge/Tropical Crtyd is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,557.

From$222/night

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9.8 ★ 101 reviews

Steps to Beach/Walk 2 Bridge St./Beach Supplies

Condo, Anna Maria Island

Steps to Beach/Walk 2 Bridge St./Beach Supplies is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Steps to Beach/Walk 2 Bridge St./Beach Supplies

Steps to Beach/Walk 2 Bridge St./Beach Supplies is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,443.

From$206/night

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Family-friendly vacation rentals in Anna Maria Island, FL

Plan a trip with stays that give families more room to spread out.

10 ★ 19 reviews

Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach

Holiday Home, Anna Maria Island

Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay…

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About Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach

Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,774.

From$396/night

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10 ★ 2 reviews

1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach!

Cottage, Anna Maria Island

1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach! is a cottage in Anna Maria Island, with easy beach access, kitchen access, and room for a group. This stay gives…

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About 1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach!

1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach! is a cottage in Anna Maria Island, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,762.

From$252/night

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10 ★ 2 reviews

Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4

Cottage, Anna Maria Island

Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4 is a cottage in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4

Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4 is a cottage in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,430.

From$347/night

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9.2 ★ 37 reviews

Cozy Family Duplex with Pool! Close to the Gulf Beaches

Holiday Home, Anna Maria Island

Cozy Family Duplex with Pool! Close to the Gulf Beaches is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Cozy Family Duplex with Pool! Close to the Gulf Beaches

Cozy Family Duplex with Pool! Close to the Gulf Beaches is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,811.

From$259/night

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Pet-friendly vacation rentals in Anna Maria Island, FL

Bring your pet along with stays that welcome four-legged travelers.

10 ★ 1 reviews

⚓Hidden Treasure Unit B! Heated Pool just 200 steps to the beach!⚓

Holiday Home, Anna Maria Island

⚓Hidden Treasure Unit B! Heated Pool just 200 steps to the beach!⚓ is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About ⚓Hidden Treasure Unit B! Heated Pool just 200 steps to the beach!⚓

⚓Hidden Treasure Unit B! Heated Pool just 200 steps to the beach!⚓ is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,759.

From$251/night

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9.8 ★ 37 reviews

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!

Holiday Home, Anna Maria Island

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly! is a holiday home in Anna Maria Island, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly! is a holiday home in Anna Maria Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,263.

From$323/night

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9.8 ★ 21 reviews

Sea Glass on Anna Maria - By Island Real Estate Vacations

Condo, Anna Maria Island

Sea Glass on Anna Maria - By Island Real Estate Vacations is a condo in Anna Maria Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Sea Glass on Anna Maria - By Island Real Estate Vacations

Sea Glass on Anna Maria - By Island Real Estate Vacations is a condo in Anna Maria Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,107.

From$301/night

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9.6 ★ 40 reviews

Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life

Holiday Home, Anna Maria Island

Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy…

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About Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life

Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,177.

From$311/night

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Vacation rentals with a pool in Anna Maria Island, FL

Add a pool to the search when you want an easy place to cool off between outings.

10 ★ 24 reviews

Single Level Home- 1 Minute Walk to the Beach- 5 minute walk to Restaurant/Shops

Holiday Home, Anna Maria Island

Single Level Home- 1 Minute Walk to the Beach- 5 minute walk to Restaurant/Shops is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay…

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About Single Level Home- 1 Minute Walk to the Beach- 5 minute walk to Restaurant/Shops

Single Level Home- 1 Minute Walk to the Beach- 5 minute walk to Restaurant/Shops is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,353.

From$336/night

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9.8 ★ 58 reviews

Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wi-Fi, Steps to the Beach!

Holiday Home, Anna Maria Island

Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wi-Fi, Steps to the Beach! is a holiday home in Anna Maria Island, with pool access and easy beach access. This stay gives travelers a…

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About Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wi-Fi, Steps to the Beach!

Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wi-Fi, Steps to the Beach! is a holiday home in Anna Maria Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,463.

From$352/night

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9.8 ★ 15 reviews

Pool, Spa, Mini Golf, Games, Beach, sleeps 6

Holiday Home, Anna Maria Island

Pool, Spa, Mini Golf, Games, Beach, sleeps 6 is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Pool, Spa, Mini Golf, Games, Beach, sleeps 6

Pool, Spa, Mini Golf, Games, Beach, sleeps 6 is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,045.

From$292/night

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9.2 ★ 107 reviews

Gorgeous Home July specials check it out, heated pool and spa, elevator

Holiday Home, Anna Maria Island

Gorgeous Home July specials check it out, heated pool and spa, elevator is a holiday home in Anna Maria Island, with pool access. This stay gives travelers a comfortable base for exploring…

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About Gorgeous Home July specials check it out, heated pool and spa, elevator

Gorgeous Home July specials check it out, heated pool and spa, elevator is a holiday home in Anna Maria Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,344.

From$335/night

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Vacation rentals with parking in Anna Maria Island, FL

Find vacation rentals that make arriving by car easier.

10 ★ 1 reviews

Steps to the beach. Pool, Observation deck with views and beach gear

Condo, Anna Maria Island

Steps to the beach. Pool, Observation deck with views and beach gear is a condo in Anna Maria Island, with pool access, easy beach access, and outdoor space. This stay gives travelers a…

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About Steps to the beach. Pool, Observation deck with views and beach gear

Steps to the beach. Pool, Observation deck with views and beach gear is a condo in Anna Maria Island, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,960.

From$280/night

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10 ★ 1 reviews

Paradise - Steps to the Beach

Holiday Home, Anna Maria Island

Paradise - Steps to the Beach is a holiday home in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Paradise - Steps to the Beach

Paradise - Steps to the Beach is a holiday home in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,990.

From$284/night

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9.8 ★ 88 reviews

Tropical Crtyd Steps to Beach & Bridge St

Condo, Anna Maria Island

Tropical Crtyd Steps to Beach & Bridge St is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Tropical Crtyd Steps to Beach & Bridge St

Tropical Crtyd Steps to Beach & Bridge St is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,443.

From$206/night

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9.6 ★ 32 reviews

Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge

Condo, Anna Maria Island

Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge

Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,443.

From$206/night

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