Vacation rentals with a pool in Anastasia Island

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Top-rated rentals with a pool in Anastasia Island

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Guest favorite

Condo in St. Augustine

4.92 out of 5 average rating, 126 reviews

Anastasia Island 1 ~ Beach, Relax & Explore

Large one-bedroom condo with open space living, kitchen and dinning room full of natural light leading from the balcony. Bedroom has a large walk-in closet and a king bed with access to balcony. The condo comes complete with a full kitchen, washer and dryer, high-speed fibre internet, pots and pans and basic pantry items. This condo sleeps up to 4 people, best suited for 2 adults and 2 children. Queen air mattress with deep sheets and topper for optimum comfort, and a single mattress in closet.

Nov 29 – Dec 6

G$31,836 GYD per night

Guest favorite

Home in Saint Augustine

4.99 out of 5 average rating, 365 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown (5 miles) and St. Augustine Beach (3 miles). The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms, ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small extra charge for 5 or more. Motorcycle friendly! We also do live on the property!

Sep 20 – 27

G$29,538 GYD per night

Guest favorite

Condo in St. Augustine

4.99 out of 5 average rating, 101 reviews

Alice's Palace Alice in Wonderland St Augustine FL

Welcome to Alice's Palace; a sophisticated twist on Alice in Wonderland. This unique Madhatter tea party styled 1 bedroom private condominium is like no other. It has a large fully equipped kitchen, spectacular forest King bedroom, onsite spa, stunning pool and hot tub. Located in the King & Bear golf community of World Golf Village and boasts 2 World Class Golf Courses-King & Bear/Slammer & Squire and just minutes from Historic Downtown St Augustine, Outlet Shopping and many amazing beaches

Feb 3 – 10

G$26,427 GYD per night

Guest favorite

Townhouse in Saint Augustine

4.99 out of 5 average rating, 103 reviews

Affordable and Ocean View Condo! Steps from Pool!

Creston House 8B is a perfect getaway location, quaint, and well maintained. It is a private apartment, including roomy living room with queen sleeper sofa, and dining room. Fully equipped kitchen is adjacent, and desk area for your computer. The bedroom includes a comfy king size bed, and 32' TV. All linens are provided. The resort is an oceanfront complex with a large pool and private beach access. Enjoy time relaxing on porch area, just steps from the large pool. Just unpack and enjoy!

Nov 30 – Dec 7

G$30,380 GYD per night

Guest favorite

Condo in St. Augustine

4.97 out of 5 average rating, 148 reviews

Ocean Front Condo only Steps to the Beach.

Self-Check-In, Covid-19 Protocol Cleaning Utilized, Ground level, oceanfront unit w/ 2 bedrooms/2 baths at Sea Place, a quaint seaside community. Has updated kitchen & walk-in shower, washer/dryer, wifi, cable & covered patio. Amenities: 2 pools (not heated), tennis, racquetball, & beach access; 4 beach chairs & umbrella provided. Located near shops, restaurants & historic St. Augustine. 2 nights min stay. Max: 4 guests. No pets (per HOA), smoking or parties please. No BBQ grill per HOA.

Mar 22 – 29

G$42,934 GYD per night

Guest favorite

Guest suite in St. Augustine

4.96 out of 5 average rating, 539 reviews

Sheepdog Hideway - close to the Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

Dec 7 – 14

G$30,542 GYD per night

Guest favorite

Condo in St. Augustine

4.88 out of 5 average rating, 182 reviews

The Salty Suite Resort style condo

This modern 1 bed/1 bath rental unit has access to a private walk way to 2 pools, beach (5 min walk from door to sand) & tennis courts all in a gated community right on famous A1A in the Oldest City in the Nation. Perfectly situated by the beach or a quick Uber ride to Downtown to check out the history of the Oldest City in the Nation & try some other great local restaurants. We provide an in room guidebook telling you all the must do's in the town & helpful hints too! See you soon!

Aug 10 – 17

G$27,449 GYD per night

Guest favorite

Guest suite in St. Augustine

4.91 out of 5 average rating, 102 reviews

Pelican-Pool & Heated Spa, Walk to the Beach!

New and cozy one bedroom first floor unit by the beach. House is located at the end of a quiet street with no through traffic. Located less than one minute walk to the beach in the heart of Butler Beach in St. Augustine. Wonderful neighborhood with quick access to Publix supermarket and other shops and restaurants. Pool is accessible to our guests year-round although is not heated. Downtown St. Augustine is only a 10 minute drive away. The house is on a dune and has a steep driveway.

Sep 27 – Oct 4

G$34,044 GYD per night

Guest favorite

Cottage in St. Augustine

4.91 out of 5 average rating, 224 reviews

Livin’ the Dream at St. Augustine Beach

Bright beachy unit with all amenities including community pool, close public beach access and essentials including bedding, towels, beach cruiser bikes and grill. Enclosed porch and outside deck are ideal for grilling out or hanging out. My home is located in Peppertree RV Resort . The public beach access is a short 10 minute walk away. The unit has parking for two vehicles with extra parking available in an overflow lot. A washer and dryer are located inside the unit.

Sep 12 – 19

G$20,119 GYD per night

Guest favorite

Guest suite in St. Augustine

4.93 out of 5 average rating, 282 reviews

Ground floor--just 365 steps to beach!

Beautiful ground floor of a two-story house only 365 steps from one of the most beautiful beaches in the United States. Close to the Ancient City, with all its amenities and attractions. Within walking distance of great restaurants and bars. Private entrance, pool, fully furnished kitchenette with Keurig type coffeemaker, Internet, Cable TV. Two bedrooms, one with a queen bed, and the other a double Murphy bed. On-site parking for one car provided.

Nov 14 – 21

G$29,378 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.98 out of 5 average rating, 213 reviews

“Little Pink House”-hidden gem in the 💗 of Uptown

Stay with us and you truly can "Have It All"!. Just steps from shopping and restaurants, yet nestled in a quiet neighborhood. Walk to St George Street, The Fort, Visitors Center, Trolley Station, Coffee Shops, The Bayfront. 7 minutes from the Beach. Relax after a day of sightseeing around the pool, and enjoy coffee or wine on the porch. Little Pink House is the guest cottage right behind Pink House Uptown Charmer. More space for your group!

Oct 17 – 24

G$34,965 GYD per night

Guest favorite

Condo in St. Augustine

4.99 out of 5 average rating, 193 reviews

Ocean Gallery: 2 pools/resort amenities

Bright, airy and beachy, this condo at Ocean Gallery pairs resort-style amenities with an exceptionally clean, stylish and comfortable condo. Perfect for a couple or one family, it sleeps up to 4 in beds (primary bed sleeps 2; pullout sofa in living area sleeps 2 additional guests - perfect for kids). You’ll be a few steps from 1 of the 2 pools, and a 5 minute leisurely stroll through the complex will take you to the beach!

Aug 4 – 11

G$47,900 GYD per night