Holiday rentals with a pool in Orange Park

4.94 out of 5 average rating, 221 reviews

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.

Home in St. Augustine

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.

Holiday home in Orange Park

A two-story house is set back on a spacious driveway, surrounded by lush trees and vegetation. A manicured lawn features well-maintained plant beds near the entrance, while the garage is visible on the left side of the structure under a clear blue sky.

4.9 out of 5 average rating, 116 reviews

Casandra House - Peaceful / Salt Pool and Hot Tub

Welcome to Casandra House. A peaceful getaway in Orange Park, FL. Located in the vicinity of Doctor's Lake, this house sits on 3/4 of an acre surrounded with trees and vegetation. It provides just enough privacy to make you feel away from everything while minutes from shops and restaurants. Home includes a large backyard, patio screen enclosure, salt pool and hot tub. About 2 1/2 miles from the Orange Park Thrasher-Horne Center and 10 miles from NAS Jacksonville. Note: No direct lake access.

A modern living area features a light-colored sofa adorned with dark cushions and a soft throw blanket. A glass coffee table is positioned on a textured area rug, complemented by a stylish floor lamp and a leafy plant beside it. A large abstract artwork adds a striking focal point.

4.88 out of 5 average rating, 121 reviews

Lake View Escape to The Exchange

Give us your worries and we will give you an escape. Welcome to the Exchange! This Orange Park unit supports your work requirements and your playful desires. Multiple high volume healthcare facilities surround the area and the Naval Air Station is in the backyard. Luxury dinning and outdoor water activities abound. This new unit offers access to a resort style salt water pool, private garages, state of the art fitness center and wellness studio, dog park, clubhouse and lounge, and much more.

4.99 out of 5 average rating, 118 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 stylish living area features a light-colored sofa adorned with dark cushions, complemented by a small round coffee table on a textured rug. A large window allows natural light in, while a simple plant adds a touch of greenery to the space.

4.88 out of 5 average rating, 107 reviews

SuperHost Special! 1BR/1BA Luxe Stay in Jax

Our stunning 1BR/1BA apt, is centrally located; whether you're seeking medical expertise at the Mayo Clinic, sun-drenched days on beautiful beaches, or the vibrant retail, dining or nightlife of St. Johns Town Center, our luxe unit is at the center of it all. We've curated our home with your comfort and lifestyle in mind, enjoy a private/quiet atmosphere with modern amenities, luxe furnishing and bedding, fully equipped kitchen, dining Area and dedicated workspace with wifi.

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.

4.92 out of 5 average rating, 155 reviews

Cozy Home with Heated Private Pool and Patio

Nice and very clean house for your vacation and a comfortable stay. Cozy sitting area with a small pool. A protective screen around the recreation area will keep you from Florida insects))). Parking for 4 cars. Our home is located in a very convenient location: Less than 1 mile to the main road I-295 as well as the Costco store and Walmart Supercenter. At the same time, the house is located in a quiet area where you will not be disturbed by the various noises of city life.

4.93 out of 5 average rating, 401 reviews

The spacious bedroom features a decorative metal canopy bed with plush pillows and a textured blanket draped over it. Natural light filters through wooden blinds, and soft lighting is provided by bedside lamps. The room's dark walls create a cozy atmosphere, with an open doorway leading to another area.

Home in Avondale

Historic Hollywood House w/Pool

Located in Avondale, this well kept 98 year old house features original hardwood floors throughout, updated kitchen. There are 2 main bedrooms, and a third with a twin bed + trundle but no door. The back yard is private with a beautiful pool (that is not heated) and cabana. Be sure to read the house rules and neighborhood description so that there are no surprises after your reservation is confirmed. Ring cameras monitor all the entrances and are motion activated.

4.97 out of 5 average rating, 478 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!

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, 316 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.

A seating area contains two black leather couches and a coffee table with decorative items. A large mural depicting a sports-themed scene is displayed above the couches. Natural light enters through glass doors, which provide access to the outdoor space, framed by dark curtains.

4.87 out of 5 average rating, 151 reviews

Jax Jaguars Family Frdly Ste w/POOL/Pet Frdly

Welcome to Jacksonville, Florida! Home of the Jacksonville Jaguars since 1993! Come and experience a stay like no other in our 1 of a kind Ultimate Jacksonville Jaguar Unit!! This unit was decorated with the fans in mind and if your are not a fan be prepared to switch over to the Jag side! Rather you are in town for business or pleasure come and experience a stay with the Home Team & head out to Jag land and get up close and personal!

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, 256 reviews

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

Welcome to our beautifully remodeled vacation home on a safe, quiet street. Enjoy a stylish full kitchen, cozy living and dining areas, and direct lake access for fishing. Conveniently located near downtown Jacksonville, with easy access to Walmart, restaurants, beaches, Blue Springs, historic sites, NAS Jax, the airport, seaport, and local colleges. We look forward to hosting you and making your stay comfortable and memorable!

Popular amenities for Orange Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 176 reviews

Home in Southbank

*Heated Pool, Hot Tub & Grill Retreat • Free Wi-Fi

4.79 out of 5 average rating, 123 reviews

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

4.97 out of 5 average rating, 58 reviews

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

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.

4.75 out of 5 average rating, 137 reviews

Private Pool Home • Quiet • Near Beaches & Dining

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, 190 reviews

Luxury Pool Retreat • Taste of Britain

4.91 out of 5 average rating, 158 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!

A bright pool area features a clear blue swimming pool bordered by a stone patio. A palm tree provides shade, and outdoor seating is visible adjacent to the pool. A barbecue grill is situated nearby against the house's light-colored exterior with large windows.

4.88 out of 5 average rating, 112 reviews

Modern 4 bedroom w/ Patio & Pool

5 out of 5 average rating, 12 reviews

Home in Orange Park

SKY Vacation Home, Private resort for your family

Condo rentals with a pool

4.94 out of 5 average rating, 141 reviews

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.

Condo in St. Augustine

Mi CASA es su CASA

4.94 out of 5 average rating, 128 reviews

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.

Condo in St. Augustine

Spanish Colonial Design One Bedroom Condominium

Condo in Ponte Vedra Beach

A spacious studio layout is showcased, featuring a king-size bed with crisp linens and a cozy pullout sofa. Light wood flooring complements the modern furnishings, while the full kitchen is visible in the background. Recessed lighting and ceiling fan add to the airy ambiance.

4.96 out of 5 average rating, 114 reviews

"Gone Coastal" is Steps From the Sand!

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.

Condo in Beaches

Ocean front Beachside Bliss

4.92 out of 5 average rating, 177 reviews

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.

Condo in Lincolnville

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

4.93 out of 5 average rating, 121 reviews

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.

Condo in Beaches

Oceanfront Oasis: Top Floor Paradise

4.97 out of 5 average rating, 227 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.

Condo in Beaches

Beachcomber Oceanfront 180* panoramic view

Condo 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

A well-appointed bedroom features a spacious bed adorned with red and white accent pillows. A textured wall art piece hangs above, while natural light filters in through the window covered by horizontal blinds. A soft blanket is neatly draped across the bed, adding comfort.

4.97 out of 5 average rating, 35 reviews

Luxurious one BD king/pool/gym

4.97 out of 5 average rating, 34 reviews

A comfortable lounge area features a spacious green sectional sofa adorned with orange accent pillows. Two woven chairs are positioned around a glass coffee table, while the natural light streams through large windows dressed in light curtains, illuminating the area and showcasing framed botanical art.

Bungalow in Jacksonville

La Hacienda Bungalow in St. John’s

A spacious outdoor pool area features a clear blue water swimming pool surrounded by lounge chairs. Nearby, a shaded seating area offers umbrellas, while the buildings in the background include balconies overlooking the pool. Lush greenery can be seen in the distance under a partly cloudy sky.

4.86 out of 5 average rating, 37 reviews

Cozy 2BR Getaway | Pool & Gym

5 out of 5 average rating, 29 reviews

Red Rose Serenity | 1BD Lux King - Southeast Jax

4.94 out of 5 average rating, 50 reviews

A serene outdoor space features a private saltwater pool, enclosed by a mesh screen. Two pink flamingo floaties rest on the water. Comfortable lounge chairs provide seating alongside lush greenery, enhancing the inviting atmosphere of the retreat.

Home in St. Johns County

Zen Flamingo: Poolside Peace Near Beaches and TPC

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, 79 reviews

Heated Pool~Spring Deal~Luxe Oasis Julington Creek

An expansive saltwater pool features both deep and shallow areas, surrounded by lush greenery. A gazebo is visible to the left, offering shade, while a well-maintained lawn extends beyond the pool. The clear blue sky reflects off the water, enhancing the tranquility of the outdoor space.

4.97 out of 5 average rating, 33 reviews

The Happy Place

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.