Vacation rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lakeside

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
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.
Home in Jacksonville
4.95 out of 5 average rating, 185 reviews

Luxury 4BR Retreat w/ Heated Pool•Taste of Britain

Experience relaxed luxury in this spacious 4BR retreat featuring a private solar-heated pool, elegant British-inspired décor, and soaring 10-ft ceilings. Designed for comfort and style, the home offers both refined touches and the space families need to unwind. Enjoy smart TVs in every room, fast Wi-Fi, a fenced backyard, hammock lounge, and poolside grill. Perfect for elevated escapes or family getaways. Pool is solar-heated; temperature varies with weather and may be cooler in colder months.

Top guest favorite
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.
Vacation home in Orange Park
4.92 out of 5 average rating, 107 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.

Guest favorite
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.
Apartment in Jacksonville
4.87 out of 5 average rating, 114 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.

Top guest favorite
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.
Home in Jacksonville
4.87 out of 5 average rating, 227 reviews

Private FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located in a safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Guest favorite
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.
Condo in St. Augustine
4.87 out of 5 average rating, 314 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!

Guest favorite
Apartment in Jacksonville
4.94 out of 5 average rating, 241 reviews

Sunset Retreat | 1BR | 1.5BA | Pool | Gym | Garage

Entire modern, luxurious, and spacious apartment. Stunning lake-front view with gorgeous sunsets. Large king bed and queen sleeper sofa provide a comfortable stay for 4. Whether your stay includes a day of shopping, a trip to golf, going to work, or to unwind at the beautiful Jacksonville beaches, you are never far from your destination. Less than 5 miles to the St. Johns Town Center, 7 miles to the nearest hospital, 11 miles to the beaches, and 6 miles to the nearest golf course.

Guest favorite
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 Jacksonville
4.93 out of 5 average rating, 149 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.

Top guest favorite
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
4.97 out of 5 average rating, 456 reviews

❤️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!

Top guest favorite
A bright living room features a white brick fireplace and a mounted television above it. Large arched windows allow natural light to fill the space, while a comfortable reclining chair and a round coffee table complement the cozy atmosphere. Decorative shelves add a personal touch.
Home in Avondale
4.99 out of 5 average rating, 179 reviews

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.

Guest favorite
An open-concept living space is highlighted by a dining area featuring a large table set for six. A comfortable sectional sofa is positioned near a fireplace, complemented by natural light streaming through sheer curtains. A ceiling fan adds to the airy ambiance.
Home in Jacksonville
4.95 out of 5 average rating, 250 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!

Guest favorite
A spacious living area features a modern sectional sofa positioned around a coffee table. Large windows allow natural light to fill the room, highlighting a stone fireplace. A flat-screen TV is mounted on the wall, complemented by decorative artwork on either side.
Home in Jacksonville
4.94 out of 5 average rating, 239 reviews

Quiet Vacation Home with Pool - Centrally Located

Enjoy your vacation in this fully renovated pool home. New floors, kitchen and appliances. Includes office and play area with mini pool table. Fully remodeled bathroom spaces. The perfect mix of classic and modern! After sunny Florida activities, feel free to take a dip in the spacious pool to cool off. Rinse off in the heated exterior shower. Your home away from home! Come enjoy your stay.

Guest favorite
A comfortable bedroom features a spacious bed with crisp white linens and a soft blue throw blanket. Decorative artwork adorns the wall above the bed, complemented by a stylish nightstand with a lamp. Natural light filters through the window, accented by sheer curtains.
Apartment in Jacksonville
4.86 out of 5 average rating, 128 reviews

Lake View King Ste Nr DWTN & NAS w/POOL/Pet Frdly

Entire suite in 5 Star Community! Nestled 0.4 miles to the 295 expressway which gives access to the city! Never the less unit provides a quiet and relaxing atmosphere providing a King bed in the master suite with a large walk in closet, large bathroom with shower, Queen bed in guest room w/guest bath. Open concept living room and kitchen with attach balcony view!!

Popular amenities for Lakeside rentals with a pool

When is the best time to visit Lakeside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,314 GYDG$40,151 GYDG$41,615 GYDG$41,615 GYDG$41,615 GYDG$41,615 GYDG$46,424 GYDG$51,861 GYDG$49,561 GYDG$44,751 GYDG$44,751 GYDG$46,006 GYD
Avg. temp13°C15°C17°C20°C24°C27°C28°C28°C26°C22°C17°C14°C

Quick stats about vacation rentals with a pool in Lakeside

  • Total vacation rentals

    Explore 10 vacation rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at G$10,456 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Lakeside vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeside rentals

  • 4.9 Average rating

    Lakeside stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Lakeside
  6. Rentals with pools