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

4.97 out of 5 average rating, 177 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 :)

4.98 out of 5 average rating, 105 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

5 out of 5 average rating, 141 reviews

Southern Charmer w/Pool - Walk to Everything!

Stellar location...easily park and walk to historic sites! Spacious and modern inside but a classic Southern home on the outside. Lots of room to grill out or lounge around the heated saline pool. Beautiful views of the famed Mission from the upper/lower porches. And you'll appreciate how well stocked this home is too...if we don't provide it you probably don't need it! If you need another rental we have a 4 bedroom w/pool right next door. It's called Walk to Everything plus pool and Cottage.

Guest house in St. Augustine

4.95 out of 5 average rating, 381 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.

4.98 out of 5 average rating, 181 reviews

Cottage in St. Augustine

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

4.99 out of 5 average rating, 103 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

4.95 out of 5 average rating, 111 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, 170 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 :)

Bungalow in St. Augustine

4.96 out of 5 average rating, 284 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.

4.91 out of 5 average rating, 140 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* No Cleaning Fee! No Surprise Fees! >HUGE screened in pool! Heat pool for $60/day or $350/wk. >500 steps to beach >3 TV's with streaming apps (not cable) >Lots of parking! >.5 miles to Publix grocery store >Short drive to marina, restaurants, boat rentals >Walk to intracoastal >Short drive to DT St. Aug >Washer + Dryer >BBQ Grill >3 days of supplies (TP, trash bags, etc.)

4.95 out of 5 average rating, 186 reviews

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley

No Cleaning Fee! 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet! Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.