
Holiday 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.

Couples clothing optional escape hot tub nude 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

Tent 2-Relax,Retreat, Revive-boutique camping -A/C
-Experience nature with all the comforts of home-A/C keeps you cool! Heater keeps you warm! - Casper King size bed, deck,fire pit, coffee maker, kayaks -Private bathhouse - Located on Black Creek - Large above ground pool with deck - Grill - Less than 15 min from grocery stores/local restaurants - 40 min from downtown Jax - 50 min to St. Augustine If having difficulty booking your preferred date or you have a group, message us for more info on 1 additional tent and cabin on property .

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!

Cheerful three bedroom home with a pool
Relax with the whole family at this peaceful place to stay. Enjoy the pool or just lay out in the pool area with friends. Have a bbq and enjoy family. Spacious backyard with two hammocks and a tree swing. Front porch has a nice sitting area and tree swing. Connect to your favorite streaming platforms on the smart TV's, tv room has karaoke and free WiFi. Board games in hall closet to enjoy with family. 3 miles from Orange Park Mall, AMC movie theatre and many restaurants just minutes away

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!

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

Private FL Home with Pool, Hot tub & Luxury Master

Private Pool Home • Quiet • Near Beaches & Dining

OP Retreat | 3BR | 2BA | Pool | Fenced | Quiet

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

Pool Home with Game Room in Heart of Jax Beach!

Quiet and Serene House with Heated pool near beach

“The Cove” on the St. John’s River

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach
Apartment rentals with a pool

Mi CASA es su CASA

Jacksonville Beach Front Paradise

Spanish Colonial Design One Bedroom Condominium

Gorgeous 2/2 condo in luxury golf community, StAug

Newly renovated! Steps to BEACH & POOL!

Beachcomber Oceanfront 180* panoramic view

Gated Sawgrass Beach Club - WALK to BEACH!

Oceanfront Condo with Views, Pool, Park
Other holiday rentals with a pool

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

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

Zen Flamingo: Poolside Peace Near Beaches and TPC

The Tiny Great Escape

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

The Waddle Inn

The Cozy Woodsy Cottage

The Lazy Cow Yurt w/ Fluffy Cows, Alpacas & Sheep!
When is the best time to visit Lakeside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 SGD | $250 SGD | $259 SGD | $259 SGD | $259 SGD | $259 SGD | $289 SGD | $323 SGD | $308 SGD | $219 SGD | $239 SGD | $236 SGD |
| 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 holiday rentals with a pool in Lakeside

Total holiday rentals
Explore 10 holiday rentals in Lakeside

Nightly prices starting at
Lakeside holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 1,210 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Lakeside holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lakeside rentals

4.8 Average rating
Lakeside stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with a washing machine and dryer Lakeside
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- House rentals Lakeside
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- Rentals with outdoor seating Lakeside
- Rentals with a firepit Lakeside
- Rentals with pools Clay County
- Rentals with pools Florida
- Rentals with pools United States
- Ponte Vedra Beach
- TIAA Bank Field
- Old A1A Beach
- Summer Haven st. Augustine FL
- San Sebastian Winery
- Vilano Beach
- Lightner Museum
- Kathryn Abbey Hanna Park
- Boneyard Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- Butler Beach
- Depot Park
- Eagle Landing Golf Club
- Pablo Creek Club
- Matanzas Beach
- Adventure Landing Jacksonville Beach
- Ironwood Golf Course
- Ravine Gardens State Park
- MalaCompra Park
- St. Augustine Alligator Farm Zoological Park
- Amelia Island State Park
- Amelia Island Lugar Lindo
- Bent Creek Golf Course




