
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.

Private Bungalow with Pool/55” tv
"The Oasis" is an cozy backyard guest room, detached and completely separate from the main house, in a beautiful outdoor oasis nestled in an older but safe neighborhood located in the center of Jacksonville, 1 block from I-95, with easy access to everything. 5-7 min (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium), Times Union Center, Mayo Clinic (15 miles), Beaches (18 miles), Airport (18 miles). NOTE: No animals/pets/children under 12.

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.

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.

Condo in St. Augustine’s World Golf Village Resort
Escape to St. Augustine and enjoy a one bedroom studio 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!

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.

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.

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.

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.

❤️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!

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.

Blue Bird Paradise
Welcome to “Bluebird Paradise”. Come visit our bright, beautiful, 400 sq. ft “Guest House”, detached from our home with a porch overlooking our beautiful Florida backyard with pool. The commute is very good; it is located less than 30 minutes from the city, 30 minutes from the beach and 30 minutes from the famous historical St Augustine. Peace and quiet await you. A guesthouse is a detached building that shares the property with the host.

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!
Popular amenities for Lakeside rentals with a pool
House rentals with a pool

Cozy ranch near Jax

Your Home Away From Home

Private Pool Home • Quiet • Near Beaches & Dining

Private oasis, heated pool, exceeds expectations

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

The House. Private Pool. Pet Friendly.Quiet area.

Peaceful Oasis Pet Friendly heated Pool & Gameroom

Pool Home with Game Room in Heart of Jax Beach!
Condo rentals with a pool

My HOUSE is your HOUSE

Riverfront direct views-Get it ALL in St Augustine

Jacksonville Beach Front Paradise

Beachcomber Oceanfront 180* panoramic view

Gated Sawgrass Beach Club - WALK to BEACH!

Luxury Golf & Spa condo in Beautiful St. Augustine

Oceanfront Condo with Views, Pool, Park

Family Beach Condo - Steps To The Sand Or Pool
Other vacation rentals with a pool

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

Cozy House mins from NAS JAX & Orange Park Mall

Mandarin Retreat: Pool*Hot tub*King bed*Smart TVs

Rest, relax, revive-lovely 1 bedroom cabin

Zen Flamingo: Poolside Peace Near Beaches and TPC

The Waddle Inn

New Screened Heated Pool with Spacious Living Area

The Cozy Woodsy Cottage
When is the best time to visit Lakeside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ690 | ﺩ.ﺇ705 | ﺩ.ﺇ731 | ﺩ.ﺇ731 | ﺩ.ﺇ731 | ﺩ.ﺇ731 | ﺩ.ﺇ815 | ﺩ.ﺇ911 | ﺩ.ﺇ870 | ﺩ.ﺇ786 | ﺩ.ﺇ786 | ﺩ.ﺇ808 |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°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 ﺩ.ﺇ184 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!
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- Rentals with pools Clay County
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- Rentals with pools United States
- EverBank Stadium
- University of Florida
- Summer Haven st. Augustine FL
- Lightner Museum
- Kathryn Abbey Hanna Park
- Fountain of Youth Archaeological Park
- St Augustine Amphitheatre
- Depot Park
- Adventure Landing Jacksonville Beach
- Ravine Gardens State Park
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- St. Augustine Alligator Farm Zoological Park
- St Johns Town Center
- Florida Museum of Natural History
- University of North Florida
- TPC Sawgrass
- Little Talbot
- Fort Clinch State Park
- Memorial Park
- Marineland Dolphin Adventure
- Anastasia State Park
- Autobahn Indoor Speedway & Events - Jacksonville, FL
- Vilano Beach Fishing Pier




