Vacation rentals in Anastasia Island, FL

Best vacation rentals and Airbnb offers in Anastasia Island, FL

Charming Condo w/ Pool 500 Yards to Beach, Near Lighthouse & Downtown

Condo, Anastasia Island

Charming Condo w/ Pool 500 Yards to Beach, Near Lighthouse & Downtown is a condo in Anastasia Island, with pool access and easy beach access. This stay gives travelers a comfortable base…

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About Charming Condo w/ Pool 500 Yards to Beach, Near Lighthouse & Downtown

Charming Condo w/ Pool 500 Yards to Beach, Near Lighthouse & Downtown is a condo in Anastasia 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, free wifi, internet, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,038.

From$91/night

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Creekside Cottage- Experience St. Aug's Newest Tiny Home

Guest House, Anastasia Island

Creekside Cottage- Experience St. Aug's Newest Tiny Home is a guest house in Anastasia Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Creekside Cottage- Experience St. Aug's Newest Tiny Home

Creekside Cottage- Experience St. Aug's Newest Tiny Home is a guest house in Anastasia Island, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $679.

From$97/night

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Casa Playa Private Home for 6!

Holiday Home, Anastasia Island

Casa Playa Private Home for 6! is a holiday home in Anastasia Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Casa Playa Private Home for 6!

Casa Playa Private Home for 6! is a holiday home in Anastasia Island, with pet-friendly space 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,136.

From$104/night

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The Nautical Clipper - Steps to Beach and Cafes

Condo, Anastasia Island

The Nautical Clipper - Steps to Beach and Cafes is a condo in Anastasia Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About The Nautical Clipper - Steps to Beach and Cafes

The Nautical Clipper - Steps to Beach and Cafes is a condo in Anastasia Island, with pool access, easy beach access, and parking. 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $831.

From$119/night

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Waterfront vacation rentals in Anastasia Island, FL

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

Treehouse By the Sea

Holiday Home, Anastasia Island

Treehouse By the Sea is a holiday home in Anastasia Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Treehouse By the Sea

Treehouse By the Sea is a holiday home in Anastasia Island, with parking. 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, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,907.

From$187/night

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Walk to Beach, Fire Pit & Pet Friendly

Holiday Home, Anastasia Island

Walk to Beach, Fire Pit & Pet Friendly is a holiday home in Anastasia Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Walk to Beach, Fire Pit & Pet Friendly

Walk to Beach, Fire Pit & Pet Friendly is a holiday home in Anastasia 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,327.

From$190/night

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Spacious king size bed beach side and sunny

Apartment, Anastasia Island

Spacious king size bed beach side and sunny is a apartment in Anastasia Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Spacious king size bed beach side and sunny

Spacious king size bed beach side and sunny is a apartment in Anastasia 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,349.

From$193/night

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Yellow Palms

Holiday Home, Anastasia Island

Yellow Palms is a holiday home in Anastasia Island, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Yellow Palms

Yellow Palms is a holiday home in Anastasia Island, with pet-friendly space 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 wifi, pet friendly, pets friendly, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,820.

From$193/night

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Vacation rentals with a pool in Anastasia Island, FL

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

Home away from home! Short walk to the beach and more! Prime Location!

Condo, Anastasia Island

Home away from home! Short walk to the beach and more! Prime Location! is a condo in Anastasia Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Home away from home! Short walk to the beach and more! Prime Location!

Home away from home! Short walk to the beach and more! Prime Location! is a condo in Anastasia 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,271.

From$182/night

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The Place to Be !! Walk 2 Beach, Restaurants, Activities

Condo, Anastasia Island

The Place to Be !! Walk 2 Beach, Restaurants, Activities is a condo in Anastasia Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About The Place to Be !! Walk 2 Beach, Restaurants, Activities

The Place to Be !! Walk 2 Beach, Restaurants, Activities is a condo in Anastasia 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,278.

From$183/night

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Walk to Beach, Restaurants - Bike to Amphitheater - Short Uber to Historic Area

Condo, Anastasia Island

Walk to Beach, Restaurants - Bike to Amphitheater - Short Uber to Historic Area is a condo in Anastasia Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Walk to Beach, Restaurants - Bike to Amphitheater - Short Uber to Historic Area

Walk to Beach, Restaurants - Bike to Amphitheater - Short Uber to Historic Area is a condo in Anastasia 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,311.

From$187/night

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Tropical Bamboo~With large above ground Pool~Outdoor Firepit.

Holiday Home, Anastasia Island

Tropical Bamboo~With large above ground Pool~Outdoor Firepit. is a holiday home in Anastasia Island, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Tropical Bamboo~With large above ground Pool~Outdoor Firepit.

Tropical Bamboo~With large above ground Pool~Outdoor Firepit. is a holiday home in Anastasia Island, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,362.

From$195/night

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Vacation rentals with parking in Anastasia Island, FL

Find vacation rentals that make arriving by car easier.

Sunny Goodstreet Bed with Breakfast!

Holiday Home, Anastasia Island

Sunny Goodstreet Bed with Breakfast! is a holiday home in Anastasia Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Sunny Goodstreet Bed with Breakfast!

Sunny Goodstreet Bed with Breakfast! is a holiday home in Anastasia Island, with parking. 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, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $834.

From$119/night

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La Casita. 2BR Family Home w/ Fire Pit Near Downtown & Beach

Holiday Home, Anastasia Island

La Casita. 2BR Family Home w/ Fire Pit Near Downtown & Beach is a holiday home in Anastasia Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About La Casita. 2BR Family Home w/ Fire Pit Near Downtown & Beach

La Casita. 2BR Family Home w/ Fire Pit Near Downtown & Beach is a holiday home in Anastasia 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $994.

From$142/night

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Rave Reviews for Waterway Views Spa Comfy Beds Bring Your Boat

Holiday Home, Anastasia Island

Rave Reviews for Waterway Views Spa Comfy Beds Bring Your Boat is a holiday home in Anastasia Island, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Rave Reviews for Waterway Views Spa Comfy Beds Bring Your Boat

Rave Reviews for Waterway Views Spa Comfy Beds Bring Your Boat is a holiday home in Anastasia Island, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,696.

From$157/night

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Yellow Palms

Holiday Home, Anastasia Island

Yellow Palms is a holiday home in Anastasia Island, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Yellow Palms

Yellow Palms is a holiday home in Anastasia Island, with pet-friendly space and parking. 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, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,332.

From$184/night

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Pet-friendly vacation rentals in Anastasia Island, FL

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

Charming 1-bedroom house in gorgeous St. Augustine - PET FRIENDLY!

Holiday Home, Anastasia Island

Charming 1-bedroom house in gorgeous St. Augustine - PET FRIENDLY! is a holiday home in Anastasia Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Charming 1-bedroom house in gorgeous St. Augustine - PET FRIENDLY!

Charming 1-bedroom house in gorgeous St. Augustine - PET FRIENDLY! is a holiday home in Anastasia 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $900.

From$129/night

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Casa Playa – Private Home for 6!

Holiday Home, Anastasia Island

Casa Playa – Private Home for 6! is a holiday home in Anastasia Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Casa Playa – Private Home for 6!

Casa Playa – Private Home for 6! is a holiday home in Anastasia 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $980.

From$140/night

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5 minutes to 2 neighborhood boat launches, several beaches,historic St Augustine

Holiday Home, Anastasia Island

5 minutes to 2 neighborhood boat launches, several beaches,historic St Augustine is a holiday home in Anastasia Island, with pet-friendly space, easy beach access, and parking. This stay…

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About 5 minutes to 2 neighborhood boat launches, several beaches,historic St Augustine

5 minutes to 2 neighborhood boat launches, several beaches,historic St Augustine is a holiday home in Anastasia Island, with pet-friendly space, easy beach access, and parking. 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,053.

From$150/night

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2/2 Condo, Ground Floor, 2 Parking Spaces, Pool

Condo, Anastasia Island

2/2 Condo, Ground Floor, 2 Parking Spaces, Pool is a condo in Anastasia Island, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring…

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About 2/2 Condo, Ground Floor, 2 Parking Spaces, Pool

2/2 Condo, Ground Floor, 2 Parking Spaces, Pool is a condo in Anastasia Island, with pet-friendly space, pool access, and parking. 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,251.

From$179/night

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Vacation rentals with a kitchen in Anastasia Island, FL

Compare stays with kitchen access for longer trips and easier meals.

Sunrise Showcase - Serene direct river view!

Condo, Anastasia Island

Sunrise Showcase - Serene direct river view! is a condo in Anastasia Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sunrise Showcase - Serene direct river view!

Sunrise Showcase - Serene direct river view! is a condo in Anastasia 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $991.

From$142/night

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Sunrise Paradise on the Intracoastal Front

Condo, Anastasia Island

Sunrise Paradise on the Intracoastal Front is a condo in Anastasia Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sunrise Paradise on the Intracoastal Front

Sunrise Paradise on the Intracoastal Front is a condo in Anastasia 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,027.

From$147/night

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The Heron House - River View

Holiday Home, Anastasia Island

The Heron House - River View is a holiday home in Anastasia Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Heron House - River View

The Heron House - River View is a holiday home in Anastasia Island, with pet-friendly space 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,243.

From$178/night

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NEW TO RENTAL PROGRAM! Atlantis 205C - Heated Pool!

Condo, Anastasia Island

NEW TO RENTAL PROGRAM! Atlantis 205C - Heated Pool! is a condo in Anastasia Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW TO RENTAL PROGRAM! Atlantis 205C - Heated Pool!

NEW TO RENTAL PROGRAM! Atlantis 205C - Heated Pool! is a condo in Anastasia 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,399.

From$200/night

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