
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.

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.

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.

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.

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.

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.

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!

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.

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!

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!

Private Pool Home • Quiet • Near Beaches & Dining
Enjoy a peaceful stay in our cozy 3-bedroom home featuring a private saltwater pool. Located in a quiet residential neighborhood, this comfortable retreat is perfect for business travelers, Mayo Clinic visitors, or anyone seeking rest and privacy. The spacious living area and fully equipped kitchen make it easy to feel at home during your stay. Relax in the screened backyard pool area — ideal for unwinding after a busy day.

Ponte Vedra Beach Condo with a View
Lakefront Condo in Players Club Villas - TPC Sawgrass. 2 story condo with both a 1st and 2nd floor master bedroom and bath. Overlooks lake and pool. Within walking distance of restaurants, bars, grocery store, shops and the Players Stadium Course and Dye's Valley Course at TPC. Short drive to beach access points. Sawgrass is 30 minutes to St. Augustine, Downtown Jacksonville and Jacksonville Airport.
Popular amenities for Lakeside rentals with a pool
House rentals with a pool

*Heated Pool, Hot Tub & Grill Retreat • Free Wi-Fi

Heated Pool/Hot Tub 1 mile to dwntn/beach

Historic Hollywood House w/Pool

Fancy Private Pool Home in Jax beach!

Beach House•TreeTop View •Gourmet Kitchen• Firepit

The Pink Cabana

Zen Flamingo: Poolside Peace Near Beaches and TPC

Unique Clear-Roof Pool Oasis: 10 min to Mayo/Beach
Condo rentals with a pool

My HOUSE is your HOUSE

St Augustine Beach, comfy condo

Oceanfront Oasis: Top Floor Paradise

Newly renovated! Steps to BEACH & POOL!

Beachcomber Oceanfront 180* panoramic view

Gated Sawgrass Beach Club - WALK to BEACH!

Luxury Golf & Spa condo in Beautiful St. Augustine

2 Bedroom Luxury Condo in World Golf Village
Other vacation rentals with a pool

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

Arthurs Lake House

4BR Home In St Johns With Enclosed Large Pool

The Cozy Nook

Private Pool |3 Bikes| Dogs Ok|1/2 Acre Wooded Lot

“The Cove” on the St. John’s River

Local Splash pad with Pool, HotTub and dual shower

SuperHost Special! 1BR/1BA Luxe Stay in Jax
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
- St Augustine Amphitheatre
- Kathryn Abbey Hanna Park
- VyStar Veterans Memorial Arena
- Fountain of Youth Archaeological Park
- Depot Park
- Saint Augustine Town Plan Historic District
- Adventure Landing Jacksonville Beach
- St Johns Town Center
- Ravine Gardens State Park
- TPC Sawgrass
- University of North Florida
- St. Augustine Alligator Farm Zoological Park
- Memorial Park
- Florida Museum of Natural History
- Lochloosa Lake
- Little Talbot
- Fort Clinch State Park
- Vilano Beach Fishing Pier
- Anastasia State Park
- Autobahn Indoor Speedway & Events - Jacksonville, FL




