Holiday rentals with a pool in Historic District, St. Augustine

4.97 out of 5 average rating, 188 reviews

Flat in St. Augustine

Traveler’s Nest of uptown St. Augustine with pool!

The Traveler's Nest is a unique and cozy studio apartment with a kitchenette, private backyard and access to a huge pool located in a quiet historic uptown St. Augustine neighborhood. It's just minutes to the Old City and Vilano Beach and Fort Mose National Park and Museum is 3min walk within the neighborhood! In addition, it's close to all your necessities (groceries, liquor store, restaurants, fast food....etc.) and there's a huge pool to relax and cool off when your not out seeing sites :)

5 out of 5 average rating, 103 reviews

Pink Palms - Heated Mermaid Pool & Cabana - Downtn

🏝️ Luxurious Private Heated Pool Home In Historic Downtown and Family Friendly! - Private Heated Pool & large backyard with tons of gorgeous palms - Outdoor cabana with grill, fans, pool table, kid toys, bocce, corn hole, recessed lights and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly - Event Venue

4.99 out of 5 average rating, 418 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 and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

Apartment in St. Augustine Beach

4.84 out of 5 average rating, 258 reviews

Ocean Side Complex w/ Heated Pool B-15

Great Condo in a Beach Side Community But just to be clear Beach Side does not mean Ocean Front you will not be able to see the Ocean from the Patio The Condo is located next to Shopping Restaurants, and Historic Downtown, Great Beaches for a relaxing stay and 2 pools 1 heated Year Round Must be 21 years old to rent IMPORTANT! This unit is DOG friendly. No other pets of any type are allowed. There is a $100 Pet Fee due when you book a reservation. I have to register them before you arrive

Guest house in St. Augustine

4.95 out of 5 average rating, 397 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.

4.93 out of 5 average rating, 152 reviews

Flat in St. Augustine

Charming Vintage Intracoastal Apartment

This breathtaking property is located on a quiet neighborhood street in Vilano Beach area on the river, minutes from the beach and a few miles from Historic Downtown St. Augustine. Apartment is on the second floor facing picturesque streets of Vilano Beach area. Waterfront private outside dining area with a grill, dock, and boardwalk are available on the waterfront side of the property. Famous local restaurants Cap's on the Water and Aunt Kate's are within walking distance from the property.

Guest suite in St. Augustine

4.9 out of 5 average rating, 107 reviews

Mermaid relaxing studio. King bed. Pool.

Dear Guests, let us introduce our "Mermaid Relaxing" studio! KING BED! This studio is a private, compact, above-garage guest suite, with a private entrance upstairs from the (shared with our family) backyard. The Mermaid suite is ideal for a couple and features a King bed! Guests have own sitting area on the deck and are welcome to share the underground pool with us. Easy, ample free parking. Breathtaking pine forest outdoor views. Free wi-fi, Netflix, and Hulu apps on smart TV are included!

4.96 out of 5 average rating, 116 reviews

Flat in Lincolnville

F2 Downtown, POOL, beaches, free parking!

Relax in the middle of Historic Lincolnville 10 minutes' walk from Flagler College, the bay area, and the main attraction. Large, heated pool (April 1 - November 1) and beautiful back yard shared by our 4 apartments. This downstairs historic apartment has all the modern conveniences with new appliances, TVs in living room and both bedrooms, free Wi-Fi, and we offer ROKU TV. We have a drip coffee maker, coffee, decaf, creamers, and sugar. Free parking on premise and free street parking.

4.98 out of 5 average rating, 188 reviews

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

4.97 out of 5 average rating, 101 reviews

Flat in St. Augustine

Very Special Apt, St Augustine Historic District

Forget your worries in this spacious and serene apartment. A large, quiet space with a fenced beautiful backyard, large pool (rare for the Historic District) and gardens. Dogs are welcome. Just steps to what the walkable city of St. Augustine has to offer. A 3 minute walk to St. George Street for food, fun and frolic. The Fort, Castillo de San Marcos; the riverfront; Flagler College Tour; St. Augustine Lighthouse, restaurants & attractions close by. The beach is a 12 minute drive.

Bungalow in St. Augustine

4.96 out of 5 average rating, 297 reviews

Coral Cottage Heated Pool / Walk to Everything

Located in the Historic Abbott District of St Augustine, Florida in the heart of it all. Walk to everything, you will never need your car! This 2-bedroom cottage has all the historic charm was lovingly updated with an open floor plan is beautifully decorated and tastefully furnished. Enjoy a five-minute walk through the neighborhood to famed Castillo De San Marcos (the fort) and Historic St. George Street in the ancient “Colonial Quarter”. Extremely clean, and well-maintained.