Vacation rentals with a pool in Lakeside

4.94 out of 5 average rating, 225 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

Downtown • Historic Whitney House • Luxury Baths!

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.

5 out of 5 average rating, 109 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

Beautiful pool home and private backyard oasis. This walkable neighborhood is quiet and popular with professionals and families. It's a short walk from many restaurants, bars, and entertainment. This home includes a heated* saltwater pool, pool table, huge covered lanai, fire pit, and campground-style grill. Enjoy this oasis, surrounded by tropical landscaping and pond. We are glad to offer a military/first responder discount of 10% per day up to $100 for your stay upon request w/ valid id.

Vacation 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.

4.89 out of 5 average rating, 118 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.

Guesthouse in Southeast Jacksonville

An outdoor seating area is presented under a wooden pergola, offering shade and comfort. Paved stone flooring enhances the space, and two benches are positioned beside the walkway. A welcoming entrance to the guest house is visible, framed by lush greenery in the background.

4.8 out of 5 average rating, 127 reviews

Mother-in-law suh-WEET

Take a break and unwind at this peaceful guest house behind 4140 Peach Drive. Cradled at the end of a friendly and established Southside Neighborhood of Beach and Peach Drive (Behind the Orange Dinosaur on Beach Blvd). We are equidistant from Downtown and the Beaches; 10-12 min drive to either. If you’re coming from the North or South end you can take Southside Blvd or 295/95 and or Butler or Beach Blvd going East/Westbound. There’s also the Beach and Peach Urban park in walking distance.

4.99 out of 5 average rating, 121 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, 111 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.

Home in Southwest Jacksonville

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, 159 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.

4.92 out of 5 average rating, 413 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.

A spacious living area features a large sectional sofa in muted grey tones, inviting relaxation. Natural light filters through the two sets of sliding glass doors, leading to an outdoor view. A television is mounted on the wall above a stylish media console, enhancing the modern decor.

4.92 out of 5 average rating, 104 reviews

Lake View Suite - POOL, Pet frdly, Nr DTWN NasJax

Brand NEW 5 Star apartment community! Conveniently located near I-295, NAS JAX and shopping and entertainment. Unit provides a quiet and relaxing atmosphere providing a Queen bed in the master suite with a large walk-in closet, large bathroom with walk in shower, open concept living room and fully stocked kitchen! Last but not least you can work from home at our spacious work area then unwind after a long day on our waterfront patio!

Home in Southwest Jacksonville

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, 258 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.

4.87 out of 5 average rating, 109 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

4.87 out of 5 average rating, 125 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 Jacksonville

Entire Fabulous Home with Inground Pool & Jacuzzi

A clear swimming pool is depicted, showcasing calm water with scattered floating toys. Sunlight reflects off the surface, creating a serene atmosphere. Surrounding the pool are several black lounge chairs, providing space for relaxation.

4.87 out of 5 average rating, 238 reviews

Private FL Home with Pool, Hot tub & Luxury Master

4.99 out of 5 average rating, 447 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.

4.76 out of 5 average rating, 139 reviews

Private Pool Home • Quiet • Near Beaches & Dining

Home in Southwest Jacksonville

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, 192 reviews

Luxury Pool Retreat • Taste of Britain

5 out of 5 average rating, 154 reviews

Home in St. Augustine

Private oasis, heated pool, exceeds expectations

4.86 out of 5 average rating, 103 reviews

A spacious pool area is surrounded by lush greenery, featuring a large, sparkling blue pool and a jetted hot tub. Lounge chairs are placed along the poolside, complemented by a shaded area for relaxation. A clear sky is visible above, enhancing the outdoor atmosphere.

Home in Jacksonville

Gorgeous Florida Pool and Spa Home

4.93 out of 5 average rating, 71 reviews

A serene view of the riverfront at sunset is captured, showcasing vibrant colors across the sky. Silhouetted palm trees frame the scene, while a sparkling pool reflects the fading light. Lounge chairs are positioned nearby, inviting relaxation outdoors.

Home in Fleming Island

Sunset River Retreat

Condo rentals with a pool

4.94 out of 5 average rating, 143 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

My HOUSE is your HOUSE

Condo in St. Augustine Beach

4.89 out of 5 average rating, 210 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

4.94 out of 5 average rating, 131 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 Jacksonville Beach

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.

4.92 out of 5 average rating, 109 reviews

Ocean front Beachside Bliss

Condo 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.

4.92 out of 5 average rating, 125 reviews

Oceanfront Oasis: Top Floor Paradise

Condo 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, 188 reviews

Newly renovated! Steps to BEACH & POOL!

Condo 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, 229 reviews

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 vacation 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.

Apartment in Orange Park

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

Cottage in Jacksonville North

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.

4.89 out of 5 average rating, 323 reviews

Salty Dolphin Cottage with Pool ❤

4.97 out of 5 average rating, 65 reviews

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

4.97 out of 5 average rating, 79 reviews

K-Pop Apartment & Great Confort - Fast WiFi

4.83 out of 5 average rating, 12 reviews

The Summer House | Private Pool, Firepit

4.91 out of 5 average rating, 94 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

5 out of 5 average rating, 12 reviews

Home in Orange Park

SKY Vacation Home, Private resort for your family

A tranquil pool area is surrounded by palm trees, featuring a spacious swimming pool with a lane for swimming. Lounge chairs are arranged along the poolside, and the building's exterior is visible in the background under a colorful sky at sunset.