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

The front entrance features a pastel green exterior with a light purple door partially open. Two large lanterns flank the door, while lush greenery frames the pathway. A small mailbox is attached to the wall beside the door.

4.98 out of 5 average rating, 110 reviews

Walk to Everything plus Pool and bonus Cottage!

Our charming 4/3.5 home with heated saline pool is a quiet retreat from a day spent exploring beautiful St. Augustine! We are Downtown just blocks from the famed Fort. So close to the action you can park the car and forget about it! And best of all you really get 2 houses in 1 (double Kitchens and Livingrooms)! Perfect for extended families or friends catching up. If you need another rental we have a 4 bedroom with pool right next door. It's called Southern Charmer w/Pool - Walk to Everything.

4.98 out of 5 average rating, 117 reviews

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** 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 ✔Self check-in & free parking

A serene outdoor space features a clear, in-ground heated pool surrounded by natural landscaping. Comfortable lounge chairs and a shaded dining area under an umbrella offer inviting spots for relaxation. A tree provides added greenery nearby, creating a tranquil, private environment.

4.87 out of 5 average rating, 119 reviews

Brand NEW Beach House with HEATED pool!

Brand NEW vacation rental in St. Augustine! Gorgeous open floor plan that was designed and built specifically as a vacation rental. This home features 3 bedrooms, 2 full baths, huge 16ft ceilings and an amazing in-ground, heated pool! Enjoy your morning coffee on the front porch with natural privacy from the beautiful oak trees or lounge by the pool and entertain on the patio. 3 blocks from the beach, a block away from the intercoastal and a quick 10 min drive to historic downtown St. Augustine!

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 129 reviews

Pink Palms *Pool* Party ~ 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 exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.

4.99 out of 5 average rating, 441 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!

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

4.94 out of 5 average rating, 220 reviews

Historic Whitney House •Designer•Steps2Attractions

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.

Guesthouse in St. Augustine

The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.

4.94 out of 5 average rating, 444 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.

A comfortable living area is showcased with a gray sofa adorned with decorative pillows. A glass coffee table sits in front, accented by a floral arrangement. Two windows provide natural light, and stylish curtains frame the view. A small bookshelf stands against the wall.

4.95 out of 5 average rating, 184 reviews

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.

4.89 out of 5 average rating, 123 reviews

A backyard features a spacious heated pool surrounded by lounge chairs and tropical foliage. A large dining table with elegant chairs is visible, along with a covered gazebo. The exterior of the house showcases classic architectural details, contributing to the inviting outdoor atmosphere.

Home in Lincolnville

The Gatsby Mansion/Heated Pool/Heart of Town

Relax and experience 100 year-old “Classic meets Chic modern” architecture and design! Come enjoy lifetime memories with your family and friends in the heart of downtown Saint Augustine. >Short walking distance to the heart of it all. >Heated Pool! (Heat available for $30 per day - Please inquire for terms and conditions) >Pet friendly for 1 dog under 50 lbs (See listing for additional details) **Wedding/Bach Groups please see additional information in other things to note section**

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.99 out of 5 average rating, 224 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 :)

4.98 out of 5 average rating, 182 reviews

An inviting exterior view of the home is presented, featuring a spacious front porch adorned with eight rocking chairs. Lush greenery and colorful plants frame the entrance, enhancing the charm of the property. A well-maintained pathway leads to the front steps, inviting guests inside.

Home in Lincolnville

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.

A serene backyard features a large swimming pool surrounded by mature greenery. Comfortable seating options are available, including lounge chairs and a small table with chairs, enhancing the outdoor relaxation area. Sunlight reflects off the pool's clear blue water, inviting refreshing moments.

4.94 out of 5 average rating, 114 reviews

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.

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor area features a small pool surrounded by lush greenery and a stone waterfall. Comfortable seating options include two lounge chairs and a sofa adorned with white cushions. A wall-mounted television is positioned above a rock feature, enhancing the space's leisure appeal.

4.96 out of 5 average rating, 25 reviews

Saragossa Poolside Paradise

4.97 out of 5 average rating, 129 reviews

Luxury pool & spa home steps to beach & 2 masters!

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

5 out of 5 average rating, 113 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

4.93 out of 5 average rating, 138 reviews

Tide Pool | 4/3 Eclectic Escape | Pool & Rooftop

5 out of 5 average rating, 8 reviews

Pelicans Paradise Pool Home —Steps to Downtown

A screened outdoor area features a heated pool with a hot tub, framed by a patio area. Comfortable seating is arranged on the side, while sun filters through the surrounding trees, creating a relaxing ambiance.

4.93 out of 5 average rating, 100 reviews

Private Heated Pool & Hot Tub 1 Block to Beach!

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.99 out of 5 average rating, 144 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

A private heated pool is surrounded by a spacious patio designed for relaxation. Comfortable lounge chairs are positioned nearby, alongside a well-maintained yard with decorative plants. The pool house features a playful mermaid mural on its exterior, adding a touch of charm to the outdoor space.

4.94 out of 5 average rating, 144 reviews

Splash & Explore

Condo rentals with a pool

A bright, enclosed balcony is depicted with a comfortable chair, a small table, and a decorative area rug. Large glass windows showcase expansive ocean views, while light wood paneling complements the aqua-tiled feature wall. Ocean breezes are welcomed through the open layout.

4.93 out of 5 average rating, 106 reviews

Newly Remodeled Ocean View Condo-Upgrades Galore!!

The living room features a sliding glass door that provides a direct view of the beach. A comfortable sofa is positioned near a coffee table, while a side table and chair complement the seating arrangement. Natural light brightens the space, enhancing coastal decor.

4.98 out of 5 average rating, 133 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

Condo in St. Augustine Beach

The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.

4.96 out of 5 average rating, 180 reviews

Newly renovated! Steps to BEACH & POOL!

A spacious living area is furnished with a large blue sectional sofa and a wooden coffee table. A ceiling fan circulates air. Natural light enters through a balcony door, offering a view of the beach and surrounding coastal decor.

4.9 out of 5 average rating, 159 reviews

Ocean Views! 4 decks Beachside of A1A. Pool!

A bright living area includes a comfortable sofa and two accent chairs arranged around a glass coffee table. Natural light enters through large windows, illuminating the space. A flat-screen television is mounted on the wall, and coastal-themed artwork adds a subtle decorative touch.

4.9 out of 5 average rating, 218 reviews

St Augustine Beach, no stairs, clean, 2 BR 2 Bath

4.98 out of 5 average rating, 105 reviews

A private balcony is presented, offering panoramic ocean views. The space includes a textured table and four chairs, with one set featuring floral upholstery. Green grass and sandy shorelines blend into the sea under a clear blue sky, enhancing the sense of tranquility.

Condo in Treasure Beach

Wade n Sea Ocean Front Condo

A spacious outdoor pool area is surrounded by lounge chairs and palm trees, providing a serene environment for relaxation. An adjacent building features balconies, offering views of the pool. A pergola is visible nearby, complementing the inviting atmosphere of the gated community.

4.93 out of 5 average rating, 124 reviews

Sun & Sea - Beach & Heated Pool, Pet Friendly!

A sunlit indoor pool area features large glass doors that open to an outdoor pool surrounded by palm trees. Comfortable lounge chairs are positioned around the poolside, creating a relaxing space for guests. A hot tub is visible in the foreground, enhancing the inviting atmosphere.

5 out of 5 average rating, 279 reviews

Ocean Gallery 1/1, 2 pools

Other vacation rentals with a pool

4.87 out of 5 average rating, 38 reviews

Sunshine Dip | Sleeps 8, Relaxing, Pool, WIFI

4.95 out of 5 average rating, 41 reviews

Home in Lincolnville

Historic Recording Studio

Two lounge chairs with blue and white stripes are positioned beside a heated swimming pool, which reflects the surrounding greenery. A shaded dining area on a wooden deck features a table and multiple chairs, inviting relaxation and outdoor dining.

4.97 out of 5 average rating, 76 reviews

Heated pool retreat! Walk to historic downtown

4.72 out of 5 average rating, 234 reviews

A clear screened enclosure surrounds a serene saline pool, reflecting the bright blue sky. A comfortable chair is situated nearby, surrounded by greenery and illustrative plants, creating a tranquil environment for relaxation.

Cottage in St. Augustine

Cozy Cottage w/Pool Downtown near Brewery & Beach!

The pool area features a large rectangular swimming pool with lounge chairs lining the sides. Palms and landscaped greenery surround the pool, creating a relaxing atmosphere. A warm sunset casts a golden glow over the scene, enhancing the coastal oasis vibe.

4.93 out of 5 average rating, 56 reviews

Luxury Costal Oasis Close to Beach & Amphitheater

Guesthouse in Lincolnville

A private pool area is surrounded by lush greenery, featuring a small, solar-heated pool set in a wooden deck. A spiral staircase leads to a balcony, and potted plants add color and texture to the serene outdoor space.

4.89 out of 5 average rating, 46 reviews

Relaxing Oasis Saint Augustine City Center

A spacious living area is highlighted by a light-toned sectional couch with soft pillows. Modern decor includes a wall-mounted TV displaying a beach scene. Nearby, a small table and chairs invite relaxation with views of the exterior landscape through large glass doors.

5 out of 5 average rating, 30 reviews

Modern Coastal Retreat

A serene outdoor area features a suspended basket chair, surrounded by lush greenery and sun loungers beside a sparkling pool. Umbrella-shaded tables provide shade, while the building's modern architecture stands in the background, enhancing the inviting atmosphere of the space.