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, 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.

4.94 out of 5 average rating, 220 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.

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 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, 154 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, 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!

4.99 out of 5 average rating, 186 reviews

A charming white house with a steeply pitched roof is framed by manicured green lawns and well-maintained shrubbery. Welcoming front steps lead to a distinctive wooden door, flanked by large windows that provide natural light to the interiors.

Home in Avondale

Avondale Retreat - Private Home with Heated Pool

Enjoy the best of both worlds in Riverside! Walk or bike to many shops and restaurants in Historic Murray Hill, Avondale and Five Points, then return to your private, peaceful backyard oasis. Relax in your heated salt water pool, grill outdoors or prepare a meal in the fully stocked kitchen and wind down with a nightcap by the fire pit. Right off I-10 and I-95, close to the Jaguar Stadium, JAX, Mayo Clinic and only 25 minutes to Jax Beaches.

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!

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, 175 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

4.79 out of 5 average rating, 121 reviews

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

4.96 out of 5 average rating, 56 reviews

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

4.99 out of 5 average rating, 442 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

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

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, 242 reviews

Private Pool Getaway • 5 min Beach • Sleeps 9

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

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 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

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!

Apartment in Fernandina Beach

A spacious living area is presented, featuring large windows that allow natural light to filter in. A light-colored sofa and two armchairs are arranged around a circular coffee table. A wall-mounted TV is positioned opposite, and greenery is visible outside through the windows.

4.92 out of 5 average rating, 122 reviews

2115 Beach Wood Amelia Island - Easy beach access!

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 St. Augustine

The bedroom features a king-size bed with a quilted bedspread and decorative pillows. A bedside lamp sits on a dark wooden nightstand. Large windows with drapes allow natural light into the space, creating a serene environment. A comfortable chair is positioned near the window.

4.97 out of 5 average rating, 103 reviews

Luxury Golf & Spa condo in Beautiful St. Augustine

Apartment in Fernandina Beach

The spacious room features two queen beds with decorative throws, offering ample space for guests. A seating area with two chairs and a small table is present, alongside a console table that adds functionality. Large windows invite natural light, creating a bright and airy environment.

4.9 out of 5 average rating, 143 reviews

Peaceful escape on the Omni Resort Island - Pool!

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.

4.98 out of 5 average rating, 63 reviews

K-Pop Apartment & Great Confort - Fast WiFi

Home in OakLeaf Plantation

4.72 out of 5 average rating, 25 reviews

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

4.94 out of 5 average rating, 49 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

5 out of 5 average rating, 48 reviews

Cozy Retreat & Canopy King Bed/Fireplace/Pool View

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