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

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Top-rated rentals with a pool in Historic District, St. Augustine

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Guest favorite

Home in St. Augustine

5 out of 5 average rating, 128 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 favorite

Home in Saint Augustine

4.99 out of 5 average rating, 388 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!

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 332 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.

Guest favorite

Rental unit in Lincolnville

4.96 out of 5 average rating, 103 reviews

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, TV's in living room and both bedrooms, wireless access and availability of Netflix, Hulu, Roku, CNN, FOX, E, Bravo, HGTV, TLC, and much more. Free parking on premise and free street parking.

Guest favorite

Home in Lincolnville

4.97 out of 5 average rating, 107 reviews

Lux Retreat|Private Pool|Walk to Nights of Lights

Relax & Reset at The Retreat - a rare private in-town getaway for two couples. Sparkling pool & tropical outdoor oasis in gorgeous designer home. Located on quiet street, 8-min walk to Historical Downtown and the hottest bars & restaurants. Spread out in 1800SF of dramatic light filled spaces - 2BD/2BA has been completely reinvented for casual, elegant living. Each bedroom features unique architectural treats - a private balcony to the east and a sun-drenched studio kitchenette to the west.

Guest favorite

Cottage in St. Augustine

4.98 out of 5 average rating, 165 reviews

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.

Guest favorite

Home in St. Augustine

4.98 out of 5 average rating, 149 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 :)

Guest favorite

Condo in St. Augustine

4.95 out of 5 average rating, 100 reviews

++Perfect Romantic Getaway - Walk to the Sea

Our Condo by the Sea bids welcome from Anastasia Island! All modern amenities. Looking for a Romantic Getaway by the Sea? Relax and really unwind! This is the getaway you have been looking for. Located right on gorgeous, white sand Crescent Beach, a couple minute's walk from your gated condo, and only 15 minutes drive up A1A to The Historic District of St. Augustine and the nightlife of the City! Close to everything. Fabulous dining and historic sights. Come to our Condo and be amazed!

Guest favorite

Bungalow in St. Augustine

4.96 out of 5 average rating, 196 reviews

Updated Cottage in Heart of Town / Park & Walk

Located in the Historic Abbott District of St Augustine, Built in 1825 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.

Guest favorite

Home in Lincolnville

4.98 out of 5 average rating, 111 reviews

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in Downtown St. Augustine.

Guest favorite

Home in St. Augustine

4.93 out of 5 average rating, 126 reviews

Bright and Airy Plantation Home

Family-sized 4-Bedroom Plantation Home--right downtown! This 3000 square foot home was originally a Nunnery that was built in 1900 and meticulously restored In 2010. Just a hop, skip and a jump to all of St. Augustine's downtown attractions and did we mention there is a pool? You and your fellow travelers will have a grand time cooking, relaxing, swimming and escaping from the hustle and bustle of the town, yet shopping, restaurants and beach... All within reach!

Superhost

Guesthouse in St. Augustine

4.89 out of 5 average rating, 427 reviews

Romantic Coastal Studio•Walk&Bike 2 Downtown/Beach

No Cleaning Fee! 4 Min Drive/ 15 Min Beautiful Walk to Historic Downtown 3 Min Drive to the Beach Guest Passes Fitness Club/Pool/Suana-Steam Rm/Yoga Looking to get away from the hustle & bustle of the city? This cottage surrounded by lush tropical garden is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a short drive away. With spacious living & modern amenities, the cottage offers maximum comfort & convenience.