Vacation rentals with a pool in St. Augustine Beach

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Top-rated rentals with a pool in St. Augustine Beach

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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

R2,889 ZAR per night

Guest favorite

Condo in St. Augustine Beach

4.85 out of 5 average rating, 197 reviews

Oceanside Condo - heated pool, hot tubs, beach

A newly renovated 4-bed beach condo decorated with a peaceful ocean theme will be the perfect beach house for your St. Augustine stay! With 2 swimming pools, 5 jacuzzis, tennis & pickleball courts, & private walkways to the beach, this centrally located spot will have you both entertained and relaxed while on vacation. The nautical tri-bunk room is fun for the family, the classic coastal master bedroom is serene, & the martini bar adds a festive element. You'll always remember this vacation!

Nov 9 – 16

R2,673 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!

Oct 12 – 19

R2,678 ZAR per night

Guest favorite

Condo in St. Augustine

4.92 out of 5 average rating, 249 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

Newly Remodeled 1 bedroom condo with King Size Bed, Queen Size Sleeper Sofa, 55" TV's in Living Room and Bedroom. Stairs to 3rd Floor unit with private patio. Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated), Shuffleboard Courts, Picnic Area with Grills & Private Beach Walkway. Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Restricted Breeds: Rottweiler, Pit Bull, Doberman, Chow, Shepherd.

Nov 11 – 18

R2,859 ZAR 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!

Nov 1 – 8

R2,583 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 15 – 22

R2,664 ZAR per night

Guest favorite

Condo in St. Augustine Beach

4.89 out of 5 average rating, 116 reviews

Memory Maker Beach Condo

Beautiful resort: 2 pools, 5 hot tubs, tennis court, ocean front complex, gated entrance. condo is in building 2 approx 100 yds from the ocean. $15 parking fee good for your entire stay. Fantastic location: walking distance to Starbuck’s & Publix, multiple fabulous restaurants, live music & the pier. The condo is stocked with a Full kitchen, beach chairs, towels & sand toys, linens, washer /dryer & keypad for easy check in & check out.

Nov 26 – Dec 3

R2,764 ZAR 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 2 – 9

R3,170 ZAR per night

Guest favorite

Condo in St. Augustine Beach

4.97 out of 5 average rating, 173 reviews

Ocean Front Gem; Top Floor Corner Unit

Top floor, direct ocean front, corner unit with elevator and beautiful views of the beach from both bedrooms, living room, dining room, kitchen and private balcony. We have upgraded the condo and believe it to be the best condo in Saint Augustine Ocean and Racquet. We also offer the condo immediately next door, Ocean Front Escape for rent: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our check in process is contact free.

Dec 7 – 14

R6,049 ZAR 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!

Dec 20 – 27

R5,545 ZAR per night

Guest favorite

Apartment in St. Augustine

4.88 out of 5 average rating, 115 reviews

Private Studio. Pool. 2 bikes for the beach

Studio has separate parking and entrance and available for 1 or 2 guests. With 2 bikes to get around its Just A short bike ride to the sands of Saint Augustine beach and all Its bars/restaurants. Easy taxi ride 4 miles to beautiful Downtown. Owner is easy going and lives separately on property. Unit is 300sf total. So If you’re big boned, older, or a complainer, it may not be for you. Guests may use the Pool.

May 9 – 16

R2,137 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.

Sep 19 – 26

R2,345 ZAR per night