Holiday Homes in Anastasia Island

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Featured Holiday Homes in Anastasia Island and around

Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

10.0 out of 10, Exceptional, (102)
"Spring Break with our college age daughters. "
Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

Relaxed Cancellation Policy! Oceanfront home with pool,hot tub, fire pit, bikes.

9.6 out of 10, Exceptional, (133)
"Lots of room, cool place. Great location!"
Relaxed Cancellation Policy! Oceanfront home with pool,hot tub, fire pit, bikes.

Tropical Winds - Heated Pool & Firepit! Walk to the Beach!

10.0 out of 10, Exceptional, (61)
"This is our third time staying at this amazing property. It’s starting to feel like our home away from home. The location is perfect, the fenced in yard is amazing and the home is so comfortable. We will be back again soon! "
Tropical Winds - Heated Pool & Firepit! Walk to the Beach!

Tidal Paradise - Heated Pool & Firepit! Walk to the Beach!

10.0 out of 10, Exceptional, (49)
"This home offers easy access to the beach by walk or short drive, a great pool and clean, simple layout."
Tidal Paradise - Heated Pool & Firepit! Walk to the Beach!

Steps to Sand, HEATED Pool, Private Access, Deck, Grill, Walk to Restaurants, $300 in Free Tickets!

10.0 out of 10, Exceptional, (38)
"Great place with a great price we could not have asked for a better vacation."
Steps to Sand, HEATED Pool, Private Access, Deck, Grill, Walk to Restaurants, $300 in Free Tickets!

Forever Sunshine - 4 houses to sand! Ocean View Home with Pool, Sleeps 10.

9.8 out of 10, Exceptional, (36)
"Property manager was very responsive with any questions and concerns. Location was perfect and home was immaculate! Will be returning!"
Forever Sunshine - 4 houses to sand! Ocean View Home with Pool, Sleeps 10.

SAVE ON AUGUST SPECIALS! 9BR OCEANFRONT ESTATE! LARGE POOL/YARD, GAME ROOM!

10.0 out of 10, Exceptional, (103)
"The property is amazing!!! Very clean, well-equipped kitchen, amazing views, great pool, access to beach was great and lots of beach accessories. Kelley was easy to deal with and very responsive to any questions I may have had. I would highly recommend staying here. "
SAVE ON AUGUST SPECIALS! 9BR OCEANFRONT ESTATE! LARGE POOL/YARD, GAME ROOM!

Lighthouse - Heated Pool & Firepit! Near: Amphitheatre, Historic Downtown, Beach

9.4 out of 10, Exceptional, (149)
"We were able to ride our bikes from the house to different places near by that were good to visit such as Anastasia SP, the Lighthouse and bridge of Lions."
Lighthouse - Heated Pool & Firepit! Near: Amphitheatre, Historic Downtown, Beach

Sapphire: Updated 2 bedroom home with private pool, hot tub, cabana, outdoor

9.8 out of 10, Exceptional, (35)
"Perfect weather all week "
Sapphire: Updated 2 bedroom home with private pool, hot tub, cabana, outdoor

LOW TIDE - 2 Beds / 1 Bath - Pet Friendly

10.0 out of 10, Exceptional, (166)
"Wonderful property close to the beach and downtown. We had a great stay."
LOW TIDE - 2 Beds / 1 Bath - Pet Friendly

NEW OCEANFRONT LISTING! TOTALLY RENOVATED 2 bed/2.5 bath Sea Place Townhome

10.0 out of 10, Exceptional, (98)
"Great property! Close to downtown and quiet area."
NEW OCEANFRONT LISTING! TOTALLY RENOVATED 2 bed/2.5 bath Sea Place Townhome

Island Breeze- Close to Beach w/ Screened Lanai/Pool

10.0 out of 10, Exceptional, (30)
"This property was everything that we could've hoped for and we would definitely stay here again without hesitatation!!"
Island Breeze- Close to Beach w/ Screened Lanai/Pool

Pool Paradise! $300 in Free Tickets, Tiki Bar, Walk or Bike Downtown Attractions, Restaurants, Bars

9.2 out of 10, Wonderful, (67)
"Clean house and the owner was always very quick to respond to any questions. "
Pool Paradise! $300 in Free Tickets, Tiki Bar, Walk or Bike Downtown Attractions, Restaurants, Bars

Sandy Feet - Heated Pool! Near: Amphitheatre, Historic Downtown, & Beach

9.4 out of 10, Exceptional, (87)
"Love St Augustine and this rental made the visit even better.Pet friendly with a pool...my chocolate lab was in heaven!Kids had a blast and we'll be back again soon."
Sandy Feet - Heated Pool! Near: Amphitheatre, Historic Downtown, & Beach

Starfish - Heated Pool & King Beds! Near: Amphitheatre, Historic Downtown, Beach

9.6 out of 10, Exceptional, (129)
"We loved our stay here and the hosts were so kind! Lovely property, would definitely stay here again :)"
Starfish - Heated Pool & King Beds! Near: Amphitheatre, Historic Downtown, Beach

Steps to Beach, Intracoastal, and Restaurants, Fenced Yard, Kayaks, $300 in Free Tickets Per Day!

9.6 out of 10, Exceptional, (59)
"Great place to stay!"
Steps to Beach, Intracoastal, and Restaurants, Fenced Yard, Kayaks, $300 in Free Tickets Per Day!

Villa Elena - Elegant Spacious House by the Beach with Large Pool & Heated Spa!

9.4 out of 10, Exceptional, (238)
"The house was spacious and close walk to the beach. The hosts were very responsive. St Augustine beaches were great. It was a wonderful stay. "
Villa Elena - Elegant Spacious House by the Beach with Large Pool & Heated Spa!

Walk Everywhere, Fenced Backyard, Hot Tub, Fire Pit, Screened Porch, Man Cave, $300 in Free Tickets!

10.0 out of 10, Exceptional, (22)
"We loved our stay. The house had a great setup for a full family to stay and was also close proximity to the beach and downtown area. Would highly recommend staying here while visiting St. Augustine! "
Walk Everywhere, Fenced Backyard, Hot Tub, Fire Pit, Screened Porch, Man Cave, $300 in Free Tickets!

FREE EV Charging Charming dog-friendly home close to historic downtown St. Augustine!

9.6 out of 10, Exceptional, (8)
"The house was in a great location and the house was very clean and spacious. We enjoyed our vacation very much!!"
FREE EV Charging Charming dog-friendly home close to historic downtown St. Augustine!

Blue Ocean ~ Excellent Location ~ One house off the Beach!

9.6 out of 10, Exceptional, (100)
"Great location beautiful beach, very convenient "
Blue Ocean ~ Excellent Location ~ One house off the Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anastasia Island Hotel Reviews