Anastasia Island vacation rentals

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Top-rated vacation rentals in Anastasia Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in St. Augustine

4.94 out of 5 average rating, 125 reviews

Saint Augustine Beach House

Conveniently located between both St. Augustine pier and Crescent beach. Walk or bike ride up the road 1/4 mile to the beach. Great area and neighborhood. Keypad private entrance for self check-in. First floor is all yours and sealed off from the upstairs in this 2 story home. One very large bedroom, living room, kitchen and full bath. It features a new king sized bed along with a 3 inch memory foam topper. This can be broken down into 2 separate xl twins if needed. Front and back decks.

Aug 16 – 23

R2,169 ZAR per night
Guest favorite

Cottage in St. Augustine

4.98 out of 5 average rating, 173 reviews

Bamboo Lane Hideaway near AMP, Downtown & Beaches

Sophisticated, tropical hideaway. Your retreat… quiet, respectful & peaceful. All are welcome here with love and respect. Perfect for singles, couples, looking to rest and relax or to explore this historic Florida shore, the ‘Bamboo lane hideaway’ offers unique accommodations complete with a custom-designed interior, laid-back beach vibe, and complimentary parking pass for downtown. Explore the nearby Lighthouse, Zoo, white-sand Beaches, Amphitheater & Downtown all less than 1.6 miles away.

Jul 12 – 19

R2,616 ZAR per night
Guest favorite

Guest suite in St. Augustine

4.84 out of 5 average rating, 321 reviews

Anastasia Island Tropical Treehouse

I am a beautiful beach house located 2 blocks from the back gate of Anastasia State Park, walking distance to the Beach, St. Augustine amphitheater, located in a quiet neighborhood on Anastasia Island. This is a perfect place to vacation while still social distancing ! Two bedroom 1 bath private upstairs with a big covered porch where ocean waves can be heard often and full moons are seen rising. It's called the treehouse because the house is surrounded by a canopy of native Florida foliage.

Oct 17 – 24

R2,172 ZAR per night

Popular amenities for Anastasia Island vacation rentals

Other great vacation rentals in Anastasia Island

Guest favorite

Guest suite in St. Augustine

4.95 out of 5 average rating, 268 reviews

*Best Location in St. Augustine*

May 30 – Jun 6

R2,060 ZAR per night
Guest favorite

Condo in St. Augustine

4.92 out of 5 average rating, 244 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

Oct 12 – 19

R2,671 ZAR per night
Guest favorite

Apartment in St. Augustine

4.97 out of 5 average rating, 266 reviews

Home away from Home close to everything!

Jul 20 – 27

R1,277 ZAR per night
Guest favorite

Apartment in St. Augustine

4.94 out of 5 average rating, 306 reviews

Comfort of Home in St Augustine

Jan 19 – 26

R2,839 ZAR per night
Guest favorite

Guesthouse in St. Augustine

4.94 out of 5 average rating, 224 reviews

Sunset Casita

Aug 25 – Sep 1

R1,863 ZAR per night
Guest favorite

Tiny home in St. Augustine

4.92 out of 5 average rating, 174 reviews

Micro Lodge STA

Aug 4 – 11

R1,785 ZAR per night
Guest favorite

Guest suite in St. Augustine

4.94 out of 5 average rating, 277 reviews

Ground floor--just 365 steps to beach!

Oct 26 – Nov 2

R2,702 ZAR per night
Guest favorite

Guesthouse in Lincolnville

4.98 out of 5 average rating, 332 reviews

Welcome to Paradise

Feb 6 – 13

R2,143 ZAR per night
Superhost

Cottage in St. Augustine

4.82 out of 5 average rating, 164 reviews

Mermaid Cove Vilano Beach/Queen. Sleeps 2. Pet fee

Nov 17 – 24

R2,479 ZAR per night
Guest favorite

Townhouse in St. Augustine

4.93 out of 5 average rating, 163 reviews

Dunewalk 1 Spacious Crescent Beach Condo

Nov 17 – 24

R2,544 ZAR per night
Guest favorite

Camper/RV in St. Augustine

4.88 out of 5 average rating, 502 reviews

Airstreamin’ in St. Augustine Beach

May 9 – 16

R1,667 ZAR per night
Guest favorite

Townhouse in Saint Augustine

4.89 out of 5 average rating, 243 reviews

St. Augustine Beach - A Townhouse Oasis!

Oct 4 – 11

R2,267 ZAR per night

Other great vacation rentals in Anastasia Island

Guest favorite

Cottage in St. Augustine

4.97 out of 5 average rating, 346 reviews

Beautiful Beach Cottage

Jan 26 – Feb 2

R3,329 ZAR per night
Guest favorite

Home in St. Augustine

4.9 out of 5 average rating, 146 reviews

Charming home with great amenities

Oct 16 – 23

R2,137 ZAR per night
Guest favorite

Guest suite in St. Augustine

4.94 out of 5 average rating, 159 reviews

Keeper's Inn

Sep 7 – 14

R2,126 ZAR per night
Guest favorite

Guesthouse in St. Augustine

4.93 out of 5 average rating, 288 reviews

10 Minutes to EVERYTHING!! Modern Serene Studio

Jul 24 – 31

R1,863 ZAR per night
Guest favorite

Cottage in Saint Augustine

4.92 out of 5 average rating, 184 reviews

119 Kings Ferry Way Historic Cottage

Oct 13 – 20

R2,280 ZAR per night
Guest favorite

Condo in St. Augustine

4.93 out of 5 average rating, 124 reviews

Anastasia Island 1 ~ Beach, Relax & Explore

Aug 14 – 21

R3,040 ZAR per night
Guest favorite

Cottage in St. Augustine

4.91 out of 5 average rating, 221 reviews

Livin’ the Dream at St. Augustine Beach

Sep 3 – 10

R1,823 ZAR per night
Guest favorite

Guest suite in St. Augustine

4.97 out of 5 average rating, 375 reviews

Winter Hawk Hideout

Aug 22 – 29

R1,661 ZAR per night
Superhost

Apartment in St. Augustine

4.88 out of 5 average rating, 524 reviews

Walk Everywhere from a Quaint Downtown Studio

Mar 1 – 8

R2,355 ZAR per night
Guest favorite

Apartment in St. Augustine

4.88 out of 5 average rating, 347 reviews

St. Augustine Studio Oasis In The Middle Of It All

R2,140 ZAR per night
Guest favorite

Townhouse in St. Augustine

4.93 out of 5 average rating, 97 reviews

Penthouse Artist Haven Ocean front Penthouse

Nov 30 – Dec 7

R6,737 ZAR per night
Guest favorite

Guesthouse in St. Augustine

4.97 out of 5 average rating, 37 reviews

MarshMellow - Island Guest Suite Amphitheater

May 1 – 8

R2,330 ZAR per night

Destinations to explore