Holiday rentals with a pool in Lakeside

4.91 out of 5 average rating, 310 reviews

A vibrant sunset casts a golden hue across the calm water, with silhouettes of docks and a distant boat in view. The sky is filled with layered clouds, creating a serene atmosphere that invites relaxation and reflection.

Home in Panama Park

Serenity and Amazing Views - Home on River w/ Pool

Beautiful House: Quiet with all amenities on deep water with pool. 12 minutes from Jax Airport, 5 min from Zoo and 10 min from Cruise Ports. Jax Beaches are just a short beautiful drive. Downtown, Stadium, Arena etc. 10 min Lounge on the deck or sit pool side while watching the sunrise/ sunset. Bring your kayaks and paddle across the river to the zoo, or find sharks teeth on the river islands. Fish off the dock and catch some of Florida's best: Reds, Trout, Flounder, Snapper, Blue Crabs.

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, 273 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.

4.94 out of 5 average rating, 218 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 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.

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, 120 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.

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, 104 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.

4.92 out of 5 average rating, 154 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

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.

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, 170 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!

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, 189 reviews

4BR w/ Pool • Sleeps 8 • Spacious Family Home

Spacious 4BR home with a private solar-heated pool, ideal for families and small groups. Features 2 king beds, 1 queen, and 2 twins, sleeping up to 8 guests. Thoughtfully styled with subtle British-inspired design touches, offering a unique and comfortable stay. Located in a quiet Panther Creek community with a fenced backyard, grill, hammock lounge, fast Wi-Fi, and smart TVs throughout. Pool is solar heated and temperature varies with weather and season.

A modern seating area features two dark leather sofas facing a wooden coffee table. Above, a vibrant mural depicts a football player, complemented by decorative plants on either side. The space is illuminated by natural light streaming through the window, framed by sheer curtains.

4.87 out of 5 average rating, 149 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!

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.

4.86 out of 5 average rating, 103 reviews

Elegant & Stylish Pool House with Arcade!

Discover the epitome of elegance and modern style at our trendy pool house, nestled in a quiet and picturesque neighborhood. With a design that seamlessly blends chic and cozy elements, this sanctuary is ideal for families or friends seeking a serene getaway. Enhance your experience with a Street Fighter arcade and board games, offering endless entertainment and a touch of nostalgia, perfect for guests of all ages.

Popular amenities for Lakeside 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, 174 reviews

Home in Southbank

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

4.87 out of 5 average rating, 123 reviews

A heated pool is surrounded by light-colored stone tiles, offering a relaxing atmosphere. Adjacent to the pool, a Jacuzzi is visible, designed with textured tiles. The area features a covered patio with a small dining set, providing an inviting space for outdoor enjoyment.

Home in Riverview

Entire Fabulous Home with Inground Pool & Jacuzzi

4.96 out of 5 average rating, 55 reviews

Home in Englewood

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

4.99 out of 5 average rating, 441 reviews

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.

Home in St. Augustine

Your Home Away From Home

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

Home in Oakleaf Plantation

4.7 out of 5 average rating, 23 reviews

4.96 out of 5 average rating, 48 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

Home in Jacksonville Beach

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.

4.91 out of 5 average rating, 153 reviews

Pool Home with Game Room in Heart of Jax Beach!

Apartment rentals with a pool

Apartment in St. Augustine

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

Apartment in St. Augustine

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, 126 reviews

Spanish Colonial Design One Bedroom Condominium

Apartment in St. Augustine Beach

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

4.92 out of 5 average rating, 143 reviews

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

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, 176 reviews

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

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, 117 reviews

Oceanfront Oasis: Top Floor Paradise

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.

4.96 out of 5 average rating, 179 reviews

Newly renovated! Steps to BEACH & POOL!

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, 225 reviews

Beachcomber Oceanfront 180* panoramic view

Apartment in Jacksonville Beach

4.9 out of 5 average rating, 135 reviews

Oceanfront Condo with Views, Pool, Park

Other holiday rentals with a pool

4.97 out of 5 average rating, 63 reviews

A spacious backyard oasis showcases a clear pool surrounded by a well-maintained patio. A green lawn area is complemented by decorative plants and gravel. A covered seating area with a dining table is visible to the side, offering a serene space for relaxation.

Flat in Orange Park

Cozy, 1-bedroom place with Private Pool and Patio.

4.97 out of 5 average rating, 33 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 Fruit Cove

The Bungalow Estate in St. John's

4.84 out of 5 average rating, 43 reviews

An aerial view showcases a private pool surrounded by a checkered patio and a lush green Astro turf area. Loungers are positioned along the poolside, and a full outdoor kitchen is visible adjacent to the pool, featuring a barbecue grill and preparation space.

Home in San Jose

Mid-century Modern Pool Paradise 🌴 📸 🔥

5 out of 5 average rating, 29 reviews

Red Rose Serenity | 1BD Lux King - Southeast Jax

Home in Green Cove Springs

An open living area features a stone fireplace as a focal point, surrounded by light-colored walls and wooden beams on the ceiling. Comfortable seating is arranged in front of the fireplace, with a television mounted nearby. The kitchen and dining area are visible in the background.

4.95 out of 5 average rating, 55 reviews

Arthurs Lake House

4.92 out of 5 average rating, 86 reviews

The exterior of a raised, single-story home is displayed, featuring a spacious deck with potted plants and outdoor seating. Sturdy wooden railings provide a welcoming touch. Surrounding greenery and a concrete area enhance the natural setting, offering a serene environment for relaxation.

Cabin in Middleburg

Rest, relax, revive-lovely 1 bedroom cabin

4.59 out of 5 average rating, 29 reviews

The exterior view of the home features a brick facade surrounded by a lush yard with various trees and greenery. A spacious pool, with natural hues of blue and tan, is visible, along with a fenced area providing privacy and relaxation.

Home in Orange Park

3BR Cottage w/Private Pool & Fenced Yard - Dogs OK