
Holiday rentals with a pool in Historic District, St. Augustine
Find and book unique homes with a pool on Airbnb
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

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.

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi DT
ISLE BE BACK 🌴— a brand NEW modern home! Dates fill quickly for spring & summer — save your stay now! Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔ Sleeps 8 comfortably ✔ Easy self check-in & free parking

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.

Downtown • Historic Luxury • DesignerKitchen&Baths
Off Street Parking 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 3-BR Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury bath. 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.

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.

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!* >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.)

Ocean Front Gem: Top Floor Corner Unit
Top floor, direct ocean front, 2 bedroom, 2 bathroom corner unit condo with elevator and unobstructed beach views from both bedrooms, living room, dining room, kitchen and private balcony in beautiful St Augustine Ocean and Racquet Resort. We also offer the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.

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.
Popular amenities for Historic District, St. Augustine rentals with a pool
House rentals with a pool

Plunge Pool, Pack N Play, BBQ, Walk Downtown

Heated Pool/Hot Tub 1 mile to dwntn/beach

Tide Pool - Heated Pool/Hot Tub/Golf Cart

Peaceful Oasis Pet Friendly heated Pool & Gameroom

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

Kid & Dog Haven: Poolside Fun in St. Augustine

Island Retreat: Pool/Hot Tub/Tiki Bar/Close2Beach

Splash & Explore
Apartment rentals with a pool

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

Sand & Surf-180° View DirectOceanfront Heated Pool

2 BR Condo in St Augustine across from Beach

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

361 Fun in the Sun | Direct Oceanfront Ground Floor

B207 Entire Oceanfront Condo Steps From Pool & Bch

Summerhouse - Direct Oceanfront Corner Unit

4Ocean Front Condo With Pool unit 4
Other holiday rentals with a pool

Historic Recording Studio

Cityside Sanctuary: Pool, Game Room, Steps to Town

luxurious oceanfront condo amazing views! King bed

Sunset Cove 2 - Pool - Sea Views - Walkable

Hot tub, pool, beach! A Million Memories

Blue Haven

Luxury Costal Oasis Close to Beach & Amphitheater

Relaxing Oasis Saint Augustine City Center
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 | $272 SGD | $257 SGD | $284 SGD | $277 SGD | $281 SGD | $347 SGD | $357 SGD | $314 SGD | $320 SGD | $338 SGD | $329 SGD | $415 SGD |
| 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 $127 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Historic District, St. Augustine holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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
- Rentals with a firepit Historic District
- Flat rentals Historic District
- Pet-friendly rentals Historic District
- Rentals with beach access Historic District
- Family-friendly rentals Historic District
- Rentals with a patio Historic District
- House rentals Historic District
- Rentals with outdoor seating 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
- 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
- VyStar Veterans Memorial Arena
- Ravine Gardens State Park
- Saint Augustine Town Plan Historic District
- St Johns Town Center
- St. Augustine Alligator Farm Zoological Park
- TPC Sawgrass
- Ocean Center
- Daytona Beach Bandshell
- University of North Florida
- Ocean Walk Shops
- Memorial Park
- Little Talbot
- Vilano Beach Fishing Pier
- Anastasia State Park
- Marineland Dolphin Adventure




