Holiday rentals with a pool in St. Johns

5 out of 5 average rating, 150 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.

Camper van/Motorhome in Jacksonville

A large swimming pool is bordered by a stone patio, featuring several loungers and umbrellas. Lush palm trees surround the area, providing a tropical feel. In the background, the river can be seen beneath a partly cloudy sky.

4.96 out of 5 average rating, 277 reviews

Couples clothing optional escape hot tub deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit.

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 Designer Home • Luxury Baths • Steps2DWTN

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.

4.95 out of 5 average rating, 184 reviews

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.

Flat in St. Augustine

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.

A spacious studio is presented featuring a comfortable king bed with a light-colored headboard. A kitchenette is visible in the background, with dark wood cabinetry and modern appliances. A cozy sitting area includes a patterned sofa and wooden coffee table, with soft lighting from bedside lamps.

4.8 out of 5 average rating, 163 reviews

Private Luxury Condo @ St. Augustine's top Resort

Looking to get away?!!! Come enjoy this one bedroom luxury St. Augustine studio 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

Flat in Ponte Vedra Beach

An aerial view of the gated Sawgrass community reveals lush landscaping and well-maintained buildings. The shimmering ocean is visible in the background, with private beach access indicated by a directional arrow. A community pool can also be seen, surrounded by palm trees and parked cars.

4.98 out of 5 average rating, 104 reviews

Light, Airy Luxury Condo with Private Beach Access

Located in the gated Sawgrass community with private beach access, this beautiful studio condo is the ideal choice for a relaxing beach vacation. The privacy and beauty of the coastline rivals any beach destination in the US. The inviting, tranquil elegance of the low country-inspired decor provides the backdrop for your best vacation yet. The vaulted ceilings of the second floor unit give a light and airy feel to the space. You will relax and unwind the moment you step through the door!

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.

4.86 out of 5 average rating, 324 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, 117 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.

A spacious living area features a light-colored sofa and armchairs arranged around a central coffee table. Natural light fills the space through large sliding doors, leading to a balcony. Contemporary lamps provide soft illumination, and a rustic side table complements the decor.

4.94 out of 5 average rating, 127 reviews

Spanish Colonial Design One Bedroom Condominium

St. Augustine lays claim to being the oldest city in the U.S. and is known for its Spanish colonial architecture. Atlantic Ocean beaches like sandy St. Augustine Beach and tranquil Crescent Beach. This unit is centrally located amongst lush green grounds, towering palm trees and gorgeous pools. All can be seen and felt from the comfort of the balcony while enjoying the breezy air and an afternoon beverage. Unfortunately it is not child proof therefore only suitable for 2 adults.

4.92 out of 5 average rating, 171 reviews

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.

Home in Ponte Vedra

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, 314 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, 109 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.

Popular amenities for St. Johns rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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

4.83 out of 5 average rating, 194 reviews

Stunning Modern Oasis with a Huge Pool

4.96 out of 5 average rating, 28 reviews

2 Ensuite BR • Pool & Gym • Near the Beach

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, 442 reviews

Your Home Away From Home

4.99 out of 5 average rating, 170 reviews

Two bright chairs are positioned around a small table on a covered porch, overlooking a turquoise swimming pool. Vibrant landscaping and a wooden fence create a tropical atmosphere. Additional seating is present by the pool, enhancing the relaxing outdoor space.

Home in Beaches

Renovated Beach House w/ Pool and Outdoor Oasis

5 out of 5 average rating, 107 reviews

A serene outdoor space is captured, featuring a heated saltwater pool surrounded by tropical landscaping. Two loungers are positioned at the water's edge, with a covered patio visible in the background. Blue skies with scattered clouds add to the tranquil atmosphere.

Home in Murray Hill

Oasis in the Hill

4.91 out of 5 average rating, 156 reviews

A sparkling blue pool is outlined by a clean white patio, featuring multiple lounge chairs positioned for relaxation. The single-story home is visible in the background, surrounded by lush greenery and trees, creating a serene outdoor environment.

Home in Beaches

Pool Home with Game Room in Heart of Jax Beach!

4.89 out of 5 average rating, 382 reviews

Retreat on the river

Superhost

A spacious backyard features a clear blue pool surrounded by a concrete deck. A large inflatable unicorn floats in the water, while a sun lounger and two patio chairs are positioned nearby. Lush greenery and trees frame the area, enhancing the serene setting.

4.87 out of 5 average rating, 105 reviews

Elegant & Stylish Pool House with Arcade!

Apartment rentals with a pool

The night view features a pool illuminated by soft blue lights, surrounded by palm trees. Relaxing lounge chairs line the poolside, and the building's windows reflect warm light, suggesting a welcoming ambiance. A fountain adds a tranquil element to the setting.

4.94 out of 5 average rating, 139 reviews

My HOUSE is your HOUSE

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, 147 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

Apartment in St. Augustine Beach

A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.

4.98 out of 5 average rating, 249 reviews

Ocean Front Gem: Top Floor Corner Unit

The living area is furnished with a comfortable sofa and armchair, providing a relaxed seating space. A media console holds a television, and large sliding doors lead to a private balcony. Natural light fills the room, highlighting a neutral color palette.

4.92 out of 5 average rating, 367 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

4.92 out of 5 average rating, 108 reviews

An aerial view captures the sandy beach stretching along the coastline, featuring clusters of umbrellas and beachgoers. The pier extends into the ocean, while a vibrant skyline of buildings is visible in the background, providing a scenic contrast to the blue waters.

Apartment in Beaches

Ocean front Beachside Bliss

Apartment in Lincolnville

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

4.92 out of 5 average rating, 177 reviews

F1, Downtown, POOL, beaches, porch, parking!

4.97 out of 5 average rating, 226 reviews

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.

Apartment in Beaches

Beachcomber Oceanfront 180* panoramic view

Apartment in Ponte Vedra Beach

4.99 out of 5 average rating, 175 reviews

Gated Sawgrass Beach Club - WALK to BEACH!

Other holiday rentals with a pool

4.96 out of 5 average rating, 56 reviews

XL family home, Pool, Pool table, Private 1 acre.

An inviting arcade room showcases a variety of classic video game consoles arranged alongside vintage arcade cabinets. A cozy black leather couch is positioned in the center, with colorful cushions and a game-themed area rug beneath. Skylights above allow natural light to fill the space.

4.88 out of 5 average rating, 84 reviews

Paradise Playhouse Sleeps 10 | Arcade | Poker Rm

Apartment in Ponte Vedra Beach

5 out of 5 average rating, 58 reviews

Cozy Beach Villa•Walk to Ocean•Sawgrass Beach Club

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

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, 16 reviews

Lakeside Leisure Escape with a Lanai & pool

A serene backyard pool area is highlighted, featuring a sparkling blue pool surrounded by lush greenery and palm trees. Comfortable lounge chairs are positioned near the water's edge, creating a peaceful setting for relaxation. The evening sky adds a gentle hue to the atmosphere.

4.97 out of 5 average rating, 76 reviews

Heated Pool~Spring Deal~Luxe Oasis Julington Creek

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, 87 reviews

Reef Retreat King Suite Saint Augustine at WGV