Holiday rentals with a pool in St. Augustine

Guest house in St. Augustine

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.98 out of 5 average rating, 192 reviews

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 :)

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.

4.86 out of 5 average rating, 116 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!

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, 436 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!

A vibrant pink flamingo float is positioned in a clear swimming pool, surrounded by manicured palm trees. In the background, a sunny outdoor space features teal chairs and a matching umbrella, contributing to a relaxed atmosphere.

4.98 out of 5 average rating, 121 reviews

HGTV DesignerHome•HeatedPool•Walk/Bike 2 Downtown

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

4.98 out of 5 average rating, 106 reviews

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

4.93 out of 5 average rating, 101 reviews

A welcoming living room features a comfortable couch and accent chairs with geometric patterns. A wooden coffee table sits in the center, surrounded by light-colored walls and wood flooring. Natural light enters from sliding glass doors that lead to a private balcony, enhancing the spacious feel.

Flat in Butler Beach

SEA & SALT|2-min walk Beach|2x Sparkling Pools

Welcome to the Sea & Salt Retreat of St. Augustine Beach! Fit 4 people in this spacious 2BR/2.5BA condo that is a 2-min walk to our beautiful white sand beach and a 1-min walk to the pool with cabana and chaise lounges. Effortlessly enjoy relaxation at the beach, lounge all day in the sun at the sparkling clean pool, or drive 12-mins to the Historic Downtown St. Augustine. Phenomenal amenities: Two sparkling clean pools, clubhouse, tennis courts, pickleball, racquetball, and basketball!!

A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.

4.97 out of 5 average rating, 189 reviews

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.

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.96 out of 5 average rating, 178 reviews

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.

A comfortable living area is showcased with a light-colored sofa and armchair. Natural light flows in through sliding glass doors. A flat-screen TV is mounted on the wall, and a coffee table rests on a wooden floor, surrounded by decorative items.

4.94 out of 5 average rating, 155 reviews

Beautiful ocean, St Augustine beach

Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Enjoy having no stairs to climb! Family friendly vacation. New king bed. Fully equipped kitchen, free WiFi, 2 pools (one heated), full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, requires $50 (cash) registration fee upon check in. There is also a flat $15 Pet Fee for guests bringing a dog. **Strictly NON-SMOKING unit**

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

4.97 out of 5 average rating, 131 reviews

Family Beach Condo - Steps To The Sand Or Pool

Our beach condo on Crescent Beach has been our family’s haven for years, and we’re excited to share it with you! The breathtaking ocean views from our living room and balcony are just the start—enjoy a renovated kitchen, comfy bedrooms, and family-friendly touches that make this place truly special. Whether you’re here to relax, explore historic St. Augustine, or enjoy the natural beauty of Anastasia State Park, we hope you’ll create lasting memories like we have!

4.93 out of 5 average rating, 153 reviews

steps to the beach, double mastersuite- pool home

Cleaned using CDC guidelines- Oasis at the beach! Brand new home just completed and designed to be a vacation rental not modified to be one. Spacious 4 bedroom hosting 2 master suites downstairs accompanied with 9' ceilings throughout the first floor including the large living room that flows to the dining, guest bath, bar, chefs kitchen and eventually the doors out the back porch, pergola, grill area, paver patio and 10x20 pool with fully fenced in yard.

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

4.93 out of 5 average rating, 172 reviews

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.)

Popular amenities for St. Augustine rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 107 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

5 out of 5 average rating, 16 reviews

Cityside Sanctuary: Pool, Game Room, Steps to Town

A screened-in pool area is surrounded by lush greenery and features a clear blue pool. Five lounge chairs and an outdoor dining table are positioned around the pool, providing ample space for relaxation and dining. Natural light filters through the screen enclosure.

4.93 out of 5 average rating, 76 reviews

Mid-Century Pool Home Between Downtown & Beach

The exterior of a newly built cottage is presented, featuring a light-colored facade with a dark metal roof. A vibrant orange front door adds a pop of color. Surrounding greenery includes potted plants and shrubs, creating a welcoming entrance. A porch area is visible with seating arrangements.

4.97 out of 5 average rating, 109 reviews

Spoonbill - Heated Swim Spa & Golf Cart

4.99 out of 5 average rating, 67 reviews

The May House - Heated Pool - Historic Downtown

4.94 out of 5 average rating, 36 reviews

Walk 2 Beach | Salt/Heat Pool | Game Room | EV

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, 106 reviews

Walk to Everything plus Pool and bonus Cottage!

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.

4.93 out of 5 average rating, 137 reviews

Splash & Explore

Apartment rentals with a pool

A vibrant sunset casts warm hues across the sky, with wispy clouds highlighted by the fading light. A palm tree stands prominently in the foreground, while a wooden boardwalk leads toward the beach and the ocean, framed by patches of greenery.

5 out of 5 average rating, 142 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

A bright living room features an open layout illuminated by natural light. Neutral-toned furniture is paired with colorful accent pillows. A natural jute rug lies beneath a low coffee table, while a ceiling fan enhances airflow. Large glass doors open to an outdoor area.

5 out of 5 average rating, 105 reviews

Seaglass Villa, a Sunny Beachside Retreat

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

Apartment 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.

4.95 out of 5 average rating, 172 reviews

Newly renovated! Steps to BEACH & POOL!

A view of the inviting swimming pool area is captured, featuring a large pool and a smaller hot tub surrounded by lounge chairs. The beach stretches out beyond, meeting the calm Atlantic Ocean under a clear blue sky, with palm trees framing the scene.

4.93 out of 5 average rating, 100 reviews

B207 Entire Oceanfront Condo Steps From Pool & Bch

A spacious balcony overlooks a sandy beach and the ocean, where gentle waves meet the shore. Palm trees are visible in the foreground, providing a tropical backdrop. Beachgoers can be seen enjoying the sun and surf under clear blue skies.

4.94 out of 5 average rating, 144 reviews

Summerhouse - Direct Oceanfront Corner Unit

A bright living area features a light-colored leather sofa facing a flat-screen TV. A wooden coffee table sits in front, complemented by a patterned area rug. Large sliding glass doors lead to a balcony, offering views of palm trees and blue skies.

4.88 out of 5 average rating, 293 reviews

Oceanside complex B35 1 Bed 1 Bath w/Heated Pool

Apartment in St. Augustine

A well-maintained outdoor pool area is framed by palm trees and lush green landscaping. The sparkling blue pool features a central fountain and is surrounded by loungers, creating a serene environment for relaxation.

4.87 out of 5 average rating, 314 reviews

Full Condo in St. Augustine’s World Golf Village

Other holiday rentals with a pool

4.85 out of 5 average rating, 46 reviews

A private outdoor space features a refreshing pool with a connected jacuzzi, surrounded by lush greenery. A shaded seating area, including a dining table, is visible on the patio. The house in the background has a second-floor balcony overlooking the yard.

Villa in St. Augustine

The Daydream at St Augustine

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.

4.95 out of 5 average rating, 20 reviews

Saragossa Poolside Paradise

Townhouse in St. Augustine Beach

An open living area is furnished with light-colored sofas and armchairs, creating a relaxed atmosphere. A round coffee table is positioned at the center, while a dining table is visible in the background. Coastal-themed artwork adorns the wall, adding a touch of color.

4.95 out of 5 average rating, 42 reviews

Cozy beach condo with two pools and garage

Cottage in St. Augustine Beach

5 out of 5 average rating, 16 reviews

Sand Pail Beach Cottage 3/2.5 +loft & heated pool

Home in St. Augustine South

5 out of 5 average rating, 22 reviews

Ping Pong• Pets• DT 10 mins• BBQ• King• Fast Wifi

A serene bedroom setting features large windows offering a direct view of the ocean and sandy beach. Bright blue skies and gentle waves create a peaceful atmosphere. A striped bedding set complements the room's beach-themed decor, promoting relaxation and comfort.

4.94 out of 5 average rating, 17 reviews

Coquina A208, Beautiful Ocean Front View

Superhost

4.86 out of 5 average rating, 7 reviews

Beacher's Lodge Oceanfront Balcony Suite #301

The outdoor pool area features a sparkling pool surrounded by paver stones. Comfortable loungers, including a sectional and two egg chairs, create inviting relaxation spots, with greenery providing a natural backdrop. String lights are hung above, enhancing the cozy ambiance of the space.