
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 :)

Pink Palms *Heated Pool* Walk to Downtown
🏝️ 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

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.

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.

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 :)

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.

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.

Lakeside Retreat |Private Pool| 8min walk Downtown
Welcome to the historical Lakeside Retreat located in the heart of the eclectic Lincolnville neighborhood of Downtown St. Augustine - Effortlessly explore the Oldest City with a quick 8min walk into the Historical Downtown for all the top historic sights, hottest bars & restaurants. 3 bedroom, 2 bathroom layout with a private, fully fenced front yard w/ sparkling clean, heated pool - Backyard is fully fenced overlooking the tranquil Lake Maria Sanchez.

F1, Downtown, POOL, beaches, porch, parking!
Relax in downtown St. Augustine, 5 - 10 minutes walk from Flagler College, and the main attractions. Large heated pool (April 1 -November 1) and back yard that is shared between our 4 apartments. This downstairs historic apartment has all the conveniences incl. TV's in living and bedroom, free WIFI and we offer Roku TV. We have a drip coffee maker, coffee, decaf, creamers, and sugar. Free parking for 1 car on premise and free street parking.

Ocean Gallery 1/1, 2 pools
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!

Secluded oasis pool home steps to the beach
In beautiful Vilano Beach Fl. New home built April 2019. Family neighborhood on dead end street. Beach entrance 50 ft to dune walkover. A 4 bedroom home has 2 masters downstairs, and 2 bedrooms upstairs with a play loft in between. Nearby restaurants, fishing, boating. Fenced back yard. We can heat the pool for $50 per day. bbq, and lounge chairs surrounding pool. Outdoor showers located near pool, beach toys , chairs.
Popular amenities for Historic District, St. Augustine rentals with a pool
House rentals with a pool

Plunge Pool, Pack N Play, BBQ, Walk Downtown

Luxury Home with Pool, Pickle Ball and Hot Tub

Heated Pool/Hot Tub 1 mile to dwntn/beach

Historic Recording Studio

steps to the beach, double mastersuite- pool home

Downtown, Pool, Hot Tub, $300 in Free Tickets!

"Once Upon A Tide" Beach House *Heated Pool* King

2 Masters-Heated Pool & Spa+1 min Walk to Beach
Condo rentals with a pool

Riverfront direct views-Get it ALL in St Augustine

Ocean Side Complex w/ Heated Pool B-15

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

Sand & Surf-180° View DirectOceanfront Heated Pool

Seaglass Villa, a Sunny Beachside Retreat

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

Seagrass Condo - ocean front, 1 bedroom/1bath

Boutique Beachside condo with easy access to beach
Other holiday rentals with a pool

Resort Style APT 1B/1B, 10 min Beach/Downtown

Beehive Bungalow -Historic Downtown-Heated Pool

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

Canopy Oaks

Historic District! Walk Downtown • Resort Access

St. Augustine Escape w/Pool, Gym, Games MORE!

Luxury Costal Oasis Close to Beach & Amphitheater

Luxury Resort Style w/ Pool & Gym close to Beach
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 | $304 AUD | $287 AUD | $316 AUD | $309 AUD | $313 AUD | $387 AUD | $398 AUD | $350 AUD | $357 AUD | $377 AUD | $367 AUD | $463 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 $141 AUD per night before taxes and fees

Verified guest reviews
Over 2,700 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
- House rentals Historic District
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- EverBank Stadium
- Daytona Boardwalk Amusements
- Summer Haven st. Augustine FL
- Lightner Museum
- Daytona Lagoon
- Kathryn Abbey Hanna Park
- Fountain of Youth Archaeological Park
- St Augustine Amphitheatre
- Adventure Landing Jacksonville Beach
- Ravine Gardens State Park
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- St. Augustine Alligator Farm Zoological Park
- St Johns Town Center
- Ocean Center
- Daytona Beach Bandshell
- University of North Florida
- TPC Sawgrass
- Ocean Walk Shops
- Little Talbot
- Memorial Park
- Anastasia State Park
- Marineland Dolphin Adventure
- Autobahn Indoor Speedway & Events - Jacksonville, FL




