Holiday Homes in Anastasia Island

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Anastasia Island

Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!
Relax on the waterfront with lounge chairs and tables, some with umbrellas, and take in the serene views from the wooden pier.

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.
Relax in this serene beachside retreat with a large bed, ceiling fan, and TV, plus a comfortable bench and stunning ocean views.

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!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and stainless steel appliances.

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!
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, plus ample storage and a spacious work surface.

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!
Enjoy a serene beach experience with access to the ocean.

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.
Enjoy stunning ocean views from the deck of this beachfront property.

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!
Walk along the oceanfront boardwalk, flanked by railings, to the beach.

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
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (150)
"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
Step out onto the deck and enjoy the view from this house, featuring a pool and a palm tree in the background.

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
Relax on the covered porch with a comfortable chair and small table, surrounded by lush greenery.

LOW TIDE - 2 Beds / 1 Bath - Pet Friendly

10.0 out of 10, Exceptional, (167)
"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
Walk along the beach pathway surrounded by lush vegetation and dunes, leading to the ocean.

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
Enjoy cooking in this well-equipped kitchen with a sink, refrigerator, and stove.

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
Enjoy a refreshing view of the outdoor pool from the comfort of your room, with access to the tiki bar and lush surroundings.

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
Outdoor pool, a heated pool

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
Outdoor pool, a heated pool

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!
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and coffee maker.

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!
Guests can enjoy a serene oceanfront experience with access to a long pier and a sandy beach.

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!
Relax in a shaded outdoor space with a deck, ceiling fan, and comfortable seating for two.

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!
Kitchen features a double sink, faucet, and dish drying rack.

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!
Enjoy a scenic view of the ocean from this beachfront property, with easy access to the beach via a well-maintained lawn and pathway.

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

9.6 out of 10, Exceptional, (100)
"Great location beautiful beach, very convenient "
The price is NZ$1,068
includes taxes & fees
4 Aug - 5 Aug
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

Marker 8 Hotel & Marina

Marker 8 Hotel & Marina

10/10 Excellent
"Good!"
Dante 1-night trip
Posted 1 day ago
Marker 8 Hotel & Marina