Holiday rentals with a pool in St. Johns

5 out of 5 average rating, 149 reviews

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

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, 217 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.

Apartment in Crescent Beach

A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.

4.97 out of 5 average rating, 101 reviews

Incredible Waterfront Townhome

As close to the water as you can get! Our building is considered the best in the complex which is waterfront, very private and peaceful. Perched on the Point we have fantastic views overlooking the intracoastal's oyster beds, mangroves, exotic birds, fish and bald eagles!. The sunsets are incredible. A fisherman's paradise. There is a private boat dock and a small boat ramp to launch your kayak. Watch dolphins put on a show almost daily from your lanai. The beach is right across the street!

A spacious living area is outlined by warm wooden floors. A dining table is flanked by cushioned chairs, while a granite countertop bar with stools offers additional seating. Soft lighting from overhead fixtures and lamps enhances the inviting atmosphere, with a large television visible in the background.

4.95 out of 5 average rating, 134 reviews

2 Bedroom Luxury Condo in World Golf Village

Looking to get away?!!! Come enjoy this two bedroom luxury St. Augustine condo located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Resort amenities at your fingertips including access to golf, multiple pools, hot tub, a full service spa, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Absolutely No Pets allowed!!! My daughter is highly allergic, and it will cause an allergic reaction

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, 320 reviews

Full Condo in St. Augustine’s World Golf Village

Escape to St. Augustine and enjoy a one bedroom condo with new brand new renovations and upgrades! Explore the resort amenities including free unlimited access to three pools, a hot tub, lighted tennis and pickleball courts, playground, and fitness center. Located within the private gates of the World Golf Village, home of the King and Bear Golf Course. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

4.99 out of 5 average rating, 113 reviews

A well-appointed bedroom features a spacious wooden sleigh bed with a light blue and white quilt. Natural light fills the room through windows with soft drapes, and a flat-screen TV is mounted on the wall opposite a matching wooden dresser and nightstand.

Home in Fruit Cove

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

Escape to our cozy retreat! You'll unwind in style with up to 6 beds in our safe neighborhood, close to Publix and restaurants. You'll explore nearby beaches, parks and attractions or day trip to St. Augustine and Orlando. You'll enjoy serene lake views and backyard fishing. You'll love our top-notch amenities, including a recreational pool with slide, lap pool, basketball, fitness center and playground. You'll create unforgettable memories - book now! We look forward to hosting you.

4.96 out of 5 average rating, 180 reviews

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.

Home in Vilano Beach

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.

4.97 out of 5 average rating, 467 reviews

A private saltwater pool is framed by lush greenery and vibrant flowers, creating a serene outdoor space. A wooden deck with seating overlooks the pool, while a stylish umbrella provides shade. A light-filled house with large windows is visible in the background.

Bungalow in Springfield

❤️Private Pool Couples Getaway- Downtown

Our place is perfect for you and your loved one to escape your daily routine, recharge, relax and reconnect. The getaway features: PRIVATE salt water POOL and Garden Spa-like bathroom with soaking tub, refreshing 24 inch rain shower. Smart TV+WIFI in every room including bathroom. Central location with close proximity to TIAA Bank Field, airport, Downtown, Florida Theater, Times Union PAC. Walking distance to local restaurants and breweries. Hope to see you soon!

Home in Ponte Vedra Beach

A contemporary home sits beside a heated pool and spa, framed by elegant palm trees. Multiple lounge chairs are positioned around the pool, with plush seating options visible on the patio. Large glass doors offer an unobstructed view of the outdoor area, inviting natural light.

4.93 out of 5 average rating, 167 reviews

Paradise Palms Estate

Located off the popular, scenic Roscoe Boulevard this home sits directly on Cabbage Creek connecting to the Intracoastal water way. Enjoy a private dock, heated pool, spa, fire pit, hammock and oasis. This contemporary home is nestled on a private street with 300 foot long driveway on an acre and is less than a mile from the world renowned TPC golf course as well as exquisite dining, luxury shopping and the historic city of St. Augustine. Plan your escape today!

Cottage in Fort George Island

A white high-top chair is positioned on a deck overlooking the calm waters of the St. Johns River. Lush greenery can be seen in the foreground, while a clear blue sky stretches above, providing a serene backdrop for relaxation.

4.88 out of 5 average rating, 312 reviews

Salty Dolphin Cottage with Pool ❤

Welcome to the Salty Dolphin—where the St. Johns River meets the Intracoastal. This peaceful riverfront townhome offers stunning views, dolphin sightings from the decks and dock, and is just 3 miles from the Atlantic—perfect for fishing. You’re minutes from JAX Airport, downtown, Amelia Island, Ribault Club, and a ferry ride from Mayport. Relax, explore, or cast a line—this hidden gem puts the best of Florida’s First Coast at your doorstep.

4.96 out of 5 average rating, 102 reviews

The image captures a spacious outdoor pool surrounded by palm trees and lounge chairs. The clear blue water reflects the sky, adding to the serene atmosphere. The condominium's architecture is visible in the background, providing a picturesque setting for relaxation.

Flat in St. Augustine

Condo near Downtown St Augustine/beach/golf

Relax with the whole family at this peaceful place to stay. Recently renovated, close to historic downtown St. Augustine & beaches & golf. Pets Welcome.Has lobby pool & hot tub, & a full health spa open to the public. AT&T Fiber wifi, two smart tv’s, full kitchen w/all needed to prepare meals, coffee maker & coffee/tea included. Lots of walking trails. Laterra Condominiums is inside The King & The Bear 24/7 gated community.

A serene backyard is showcased, featuring a refreshing saltwater pool surrounded by smooth concrete. Lush palm trees add greenery, while the sky glows with shades of pink and purple at sunset, creating a calm outdoor environment for relaxation.

4.77 out of 5 average rating, 136 reviews

Private Pool Home • Quiet • Near Beaches & Dining

Enjoy a peaceful stay in our cozy 3-bedroom home featuring a private saltwater pool. Located in a quiet residential neighborhood, this comfortable retreat is perfect for business travelers, Mayo Clinic visitors, or anyone seeking rest and privacy. The spacious living area and fully equipped kitchen make it easy to feel at home during your stay. Relax in the screened backyard pool area — ideal for unwinding after a busy day.

Popular amenities for St. Johns rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.78 out of 5 average rating, 119 reviews

*Putt Putt Pool Home* Mini Golf/Grill/Ping Pong

4.83 out of 5 average rating, 192 reviews

A modern living area features a sleek white sofa positioned in front of a large wall-mounted TV displaying vibrant colors. Bright recessed lighting highlights the space, while large windows with blinds allow natural light to fill the room. A decorative electric fireplace adds a contemporary touch.

Home in Orange Park

Stunning Modern Oasis with a Huge Pool

A welcoming living area is depicted, featuring a spacious sofa with decorative cushions and a rectangular glass coffee table. A large TV stands on a media console, and a ceiling fan provides airflow. The open layout connects to the dining area in the background.

4.95 out of 5 average rating, 253 reviews

Sunset near the Lake/12guests/4bdrs/2baths

A private swimming pool is surrounded by a spacious patio, featuring white lounge chairs and two large umbrellas for shade. Comfortable blue seating is positioned nearby, offering a relaxed outdoor gathering space. Lush greenery forms the backdrop, enhancing the tranquil setting.

4.89 out of 5 average rating, 239 reviews

Private Pool Getaway • 5 min Beach • Sleeps 9

4.93 out of 5 average rating, 152 reviews

The pool area is enclosed by a protective screen, illuminated by soft lighting, creating a serene atmosphere. The turquoise water reflects a tranquil ambiance, while the surrounding space is designed for relaxation and recreation.

Home in Argyle Forest

Cozy Home with Heated Private Pool and Patio

A private pool is set within a fenced backyard, surrounded by lush greenery. The pool features a smooth, curving shape with clear water reflecting the blue sky. Paved stone decking offers a comfortable area for lounging and relaxing near the water.

4.95 out of 5 average rating, 187 reviews

Luxury 4BR Retreat w/ Heated Pool•Taste of Britain

4.97 out of 5 average rating, 127 reviews

Home in Flagler Beach

Walk to Beach | Pool, Spa & Private Dock

4.89 out of 5 average rating, 380 reviews

Retreat on the river

Apartment rentals with a pool

Apartment in Jacksonville Beach

A light-filled living area features a comfortable blue sectional sofa, complemented by a neutral ottoman. Large windows offer expansive views of the outdoor landscape, with greenery and palm trees visible. Soft decor accents in blue and gray enhance the serene atmosphere.

4.9 out of 5 average rating, 287 reviews

Jacksonville Beach Front Paradise

Apartment in Butler Beach

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, 144 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

A balcony view showcases a serene pool surrounded by lush green palm trees and well-maintained grounds. Comfortable outdoor seating is positioned near a glass table, while the sky features fluffy clouds and hints of blue.

4.94 out of 5 average rating, 124 reviews

Spanish Colonial Design One Bedroom Condominium

Apartment in Butler Beach

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, 105 reviews

Newly Remodeled Ocean View Condo-Upgrades Galore!!

Apartment in Jacksonville Beach

A vibrant sunset casts warm orange and pink hues across the sky, reflecting on the calm ocean waters. The beach is visible below, with gentle waves lapping at the shore. Lush green dunes frame the scene, creating a serene coastal atmosphere.

4.95 out of 5 average rating, 116 reviews

Oceanfront Oasis: Top Floor Paradise

Apartment in Jacksonville Beach

An aerial view showcases the expansive sandy beach bordered by gentle waves and the ocean. Towering buildings are visible in the background, with the highlighted condo location marked in red. Sunbathers and walkers can be seen along the shoreline, emphasizing the beach's inviting atmosphere.

4.97 out of 5 average rating, 223 reviews

Beachcomber Oceanfront 180* panoramic view

Apartment in Ponte Vedra Beach

A spacious room is furnished with two large beds and a comfortable seating area, complemented by a dresser and a television. Natural light enters through large windows, adorned with light curtains, creating an airy ambiance. A soft rug covers the carpeted floor.

4.99 out of 5 average rating, 173 reviews

Gated Sawgrass Beach Club - WALK to BEACH!

Apartment in Butler Beach

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.

4.98 out of 5 average rating, 103 reviews

Wade n Sea Ocean Front Condo

Other holiday rentals with a pool

A large zero-entry pool is framed by palm trees and lounge chairs, creating a spacious area for relaxation. A stylish community building is visible in the background, offering a welcoming presence amidst the landscaped surroundings.

5 out of 5 average rating, 14 reviews

Lakeside Leisure Escape with a Lanai & pool

The exterior of a two-story townhouse is showcased, featuring a well-maintained landscape with trimmed shrubs and a concrete pathway. A garage is visible on the left side, and large windows provide natural light. The earthy tones of the building complement the surrounding greenery.

4.9 out of 5 average rating, 10 reviews

Townhouse in St. Augustine, Florida

5 out of 5 average rating, 10 reviews

Modern pool home in the heart of Saint Johns

5 out of 5 average rating, 6 reviews

Modern Sanctuary

The master bedroom features a modern design with a large headboard and two bedside tables. A gallery of framed botanical prints adorns the wall above the bed, while lamps with purple shades provide soft lighting on either side.

4.99 out of 5 average rating, 82 reviews

Reef Retreat King Suite Saint Augustine at WGV

4.94 out of 5 average rating, 79 reviews

Luxury home-6 guests-pool. Gated golf community

A spacious living area showcases a blue sectional sofa and a circular ottoman. An elegant glass coffee table sits between, while a round dining table with orange chairs is visible in the background. The kitchen is accessible through an open layout, featuring light wooden flooring.

4.84 out of 5 average rating, 31 reviews

Family Retreat in Saint Johns-Close to Everything

A spacious sunlit lanai features a foosball table positioned near comfortable seating. Large glass doors provide a view of the heated pool and outdoor area, while a fan is installed for airflow, creating a relaxing environment for leisure activities.