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.

Dec 21 – 28

R3,106 ZAR per night

Guest favorite

Home in Saint Augustine

4.99 out of 5 average rating, 364 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 28 – Oct 5

R2,663 ZAR per night

Guest favorite

Condo in St. Augustine

4.99 out of 5 average rating, 100 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

Apr 19 – 26

R2,378 ZAR per night

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 295 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

Sep 23 – 30

R2,614 ZAR 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!

Apr 17 – 24

R2,733 ZAR per night

Guest favorite

Condo in St. Augustine

4.89 out of 5 average rating, 120 reviews

St Augustine Beach, comfy condo

Relax on the beach or unwind at the pools. Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Although not beachfront, you're an 8 minute walk on property to beach. New beach chairs, umbrella, and beach mat. Fully equipped kitchen, free WiFi, 2 pools (one heated), fitness room access, full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, $50 cash registration fee, **Strictly NON-SMOKING**

Aug 18 – 25

R3,103 ZAR per night

Guest favorite

Guest suite in St. Augustine

4.96 out of 5 average rating, 536 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.

Oct 31 – Nov 7

R2,635 ZAR per night

Guest favorite

Condo in St. Augustine

4.88 out of 5 average rating, 181 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!

Jan 21 – 28

R2,592 ZAR 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.

Oct 9 – 16

R1,810 ZAR 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.

Jan 11 – 18

R2,643 ZAR per night

Guest favorite

Guesthouse in St. Augustine

4.98 out of 5 average rating, 211 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!

Sep 26 – Oct 3

R3,146 ZAR per night

Guest favorite

Apartment in St. Augustine

4.95 out of 5 average rating, 167 reviews

Updated and clean, private beach access condo

Ground floor unit, all newly refurbished. 2 Bedrooms, 2 Baths, laptop friendly workspace and reliable WiFi. Steps from the beach, 10 min from historic downtown St. Augustine. Parking in front of Condo. Pool, beach private access. Master has en suite, separate second full bath. All new furniture, floors, counters , and appliances. Request renter to be 21yo and older. NO PETS please.

Nov 10 – 17

R2,323 ZAR per night