
Holiday rentals with a pool in Historic District, St. Augustine
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Top-rated rentals with a pool in Historic District, St. Augustine
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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 :)

Historic St. Augustine 2/1 Cottage & Heated Pool
About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

Welcome to Pink Palms - Heated Pool - Walk to DT
🏝️ 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

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

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool
1 Bedroom interior Condo in Oceanfront Complex (no view of the ocean) King Bed, Queen Sleeper Sofa, TV's in Living Room and Bedroom, 1st Floor unit with screened patio, Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated) Shuffleboard Courts, Picnic Area & Private Beach Walkway. Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Restricted Breeds: Rottweiler, Pit bull, Doberman, Chow, German Shepherd.

Downtown HistoricLuxury • Designer Kitchen & Baths
Off Street Parking for 2 vehicles 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.

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.

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

Heated Pool Beach Bungalow Steps to the Ocean
Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

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.

Beach Condo, Pools, Bikes, Short Walk to Beach
Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

Pool home oasis steps to ocean
Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.
Popular amenities for Historic District, St. Augustine rentals with a pool
House rentals with a pool

Luxury Home with Pool, Pickle Ball and Hot Tub

Luxury heated pool steps from the beach -pool bar!

Tide Pool - Heated Pool/Hot Tub/Golf Cart

Lakeside Retreat |Private Pool| 8min walk Downtown

The May House - Heated Pool - Historic Downtown

Peaceful Oasis Pet Friendly heated Pool & Gameroom

FamilyEscape Heated Pool, PacMan, Golf & FirePit

Island Retreat: Pool/Hot Tub/Tiki Bar/Close2Beach
Condo rentals with a pool

Oceanfront 1 BR Condo w/Private Balcony 2nd Floor

++Perfect Romantic Getaway - Walk to the Sea

Ocean Front Gem: Top Floor Corner Unit

Sand & Surf! Nights of Light Deals-Oceanfront Pool

Oceanside Condo-2 pools, 5 hot tubs, pickleball

Coastal 2 BR condo Near Beach-A Piece of Paradise!

Seagrass Condo - ocean front, 1 bedroom/1bath

Sun & Sea | 2 pools - 1 heated!
Other holiday rentals with a pool

The Daydream at St Augustine

Music on Marilyn- Steps from the Amp! •Jacuzzi•

St Augustine Luxury Resort Living on the Island!

Cozy Cottage w/Pool Downtown near Brewery & Beach!

Luxury Costal Oasis Close to Beach & Amphitheater

Luxury Resort Style w/ Pool & Gym close to Beach

The Blue Dream Bungalow

Casita by the Sea - Ground Level - Heated Pool
When is the best time to visit Historic District, St. Augustine?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $321 AUD | $303 AUD | $334 AUD | $327 AUD | $331 AUD | $409 AUD | $421 AUD | $370 AUD | $377 AUD | $351 AUD | $327 AUD | $336 AUD |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in Historic District, St. Augustine

Total holiday rentals
Explore 40 holiday rentals in Historic District, St. Augustine

Nightly prices starting at
Historic District, St. Augustine holiday rentals start at $149 AUD per night before taxes and fees

Verified guest reviews
Over 3,450 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Historic District, St. Augustine holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Historic District, St. Augustine rentals

4.8 Average rating
Historic District, St. Augustine stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Family-friendly rentals Historic District
- Pet-friendly rentals Historic District
- Apartment rentals Historic District
- House rentals Historic District
- Rentals with outdoor seating Historic District
- Rentals with a fire pit Historic District
- Rentals with a patio Historic District
- Rentals with beach access Historic District
- Rentals with a fireplace Historic District
- Rentals with a washing machine and dryer Historic District
- Rentals with pools St. Augustine
- Rentals with pools St. Johns County
- Rentals with pools Florida
- Rentals with pools United States
- Ponte Vedra Beach
- EverBank Stadium
- Old A1A Beach
- Summer Haven st. Augustine FL
- San Sebastian Winery
- Daytona Boardwalk Amusements
- Vilano Beach
- Daytona Lagoon
- Lightner Museum
- Boneyard Beach
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- Crescent Beach
- Butler Beach
- Matanzas Beach
- Pablo Creek Club
- Eagle Landing Golf Club
- Ravine Gardens State Park
- MalaCompra Park
- St. Augustine Alligator Farm Zoological Park
- Adventure Landing Jacksonville Beach
- Neptune Approach
- Amelia Island State Park
- Amelia Island Lugar Lindo




