Vacation rentals with a pool in Lakeside

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.

4.91 out of 5 average rating, 310 reviews

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.

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.

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.

4.9 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.

Apartment in Southwest Jacksonville

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 swimming pool is enclosed within a screened area, providing a bug-free environment. Lounge chairs are positioned nearby, and a leafy plant adds a touch of greenery. The background features a single-story home and a well-maintained backyard, surrounded by a wooden fence.

4.86 out of 5 average rating, 290 reviews

Sunny Florida home with a pool.

Enjoy a stylish experience at this beautiful home that is 16 minutes from the beach, 15 mins from Mayo Clinic and downtown. This home has two bedrooms, two bathrooms, living room, porch, and swimming pool. The living room has a couch that unfolds to a bed. The pool has a screen room around it to keep all the bugs out. There is a smart tv in each bedroom and living room. The house also includes high speed internet and a fence around the backyard. You can enjoy a nice cookout in the backyard.

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.

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, 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 Palm Valley

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 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.

4.88 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.

Apartment in Southwest Jacksonville

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, 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!

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, 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

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.

4.87 out of 5 average rating, 123 reviews

Entire Fabulous Home with Inground Pool & Jacuzzi

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 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

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

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, 156 reviews

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.

4.87 out of 5 average rating, 110 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

Home in Jacksonville Beach

An illuminated heated saltwater pool captures attention under the evening sky. The space features a spa connected to the pool, surrounded by a screened enclosure, providing a serene outdoor atmosphere. Comfortable lounge chairs accompany an outdoor dining area with a grill in the background.

4.89 out of 5 average rating, 190 reviews

Private Resort Retreat | Pool, Spa + Golf Cart

Condo 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

Condo in St. Augustine Shores

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 123 reviews

Riverfront direct views-Get it ALL 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

Condo in St. Augustine Beach

4.99 out of 5 average rating, 103 reviews

Home away from home! Short walk to beach & more!

Condo in St. Augustine Beach

The living room features beach-themed decor, with turquoise walls and comfortable sofas. A surfboard is mounted on the wall, and decorative cushions are arranged on the sofas. A light blue coffee table sits on a striped rug, while natural light enters through the window.

4.91 out of 5 average rating, 198 reviews

Unwind, relax and enjoy! King bed - beach items

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, 108 reviews

Ocean front Beachside Bliss

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, 226 reviews

Beachcomber Oceanfront 180* panoramic view

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

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.

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

Home in OakLeaf Plantation

4.72 out of 5 average rating, 25 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.

4.84 out of 5 average rating, 43 reviews

Mid-century Modern Pool Paradise 🌴 📸 🔥

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

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