
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.

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.

Private oasis, heated pool, exceeds expectations
Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Oasis in the Hill
Beautiful pool home and private backyard oasis. This walkable neighborhood is quiet and popular with professionals and families. It's a short walk from many restaurants, bars, and entertainment. This home includes a heated* saltwater pool, pool table, huge covered lanai, fire pit, and campground-style grill. Enjoy this oasis, surrounded by tropical landscaping and pond. We are glad to offer a military/first responder discount of 10% per day up to $100 for your stay upon request w/ valid id.

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.

SuperHost Special! 1BR/1BA Luxe Stay in Jax
Our stunning 1BR/1BA apt, is centrally located; whether you're seeking medical expertise at the Mayo Clinic, sun-drenched days on beautiful beaches, or the vibrant retail, dining or nightlife of St. Johns Town Center, our luxe unit is at the center of it all. We've curated our home with your comfort and lifestyle in mind, enjoy a private/quiet atmosphere with modern amenities, luxe furnishing and bedding, fully equipped kitchen, dining Area and dedicated workspace with wifi.

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.

❤️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!

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

Entire Fabulous Home with Inground Pool & Jacuzzi

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

Your Home Away From Home

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

San Marco Home • Pool, Hot Tub, Grill

Clear-Roof Heated Pool • Luxury All-Season Swim

Modern 4 bedroom w/ Patio & Pool

SKY Vacation Home, Private resort for your family
Apartment rentals with a pool

My HOUSE is your HOUSE

Beachy Condo| Steps to Beach | Pools | Hot Tubs

Spanish Colonial Design One Bedroom Condominium

Ocean front Beachside Bliss

F1, Downtown, POOL, beaches, porch, parking!

Oceanfront Oasis: Top Floor Paradise

Newly renovated! Steps to BEACH & POOL!

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

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

Zen Flamingo: Poolside Peace Near Beaches and TPC

Guest Favorite! 8th Floor Luxe King Suite PetOK

Rare Downtown Oasis | Private Pool + Parking

Cottage on River

The Happy Place

Beautiful Waterfront Sawgrass Players Club Villa!

Pool - Sleeps 10 - Playstation 5 + Air Hockey
When is the best time to visit Lakeside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $250 SGD | $265 SGD | $254 SGD | $254 SGD | $254 SGD | $254 SGD | $284 SGD | $317 SGD | $303 SGD | $273 SGD | $273 SGD | $281 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 $64 SGD per night before taxes and fees

Verified guest reviews
Over 1,030 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

4.9 Average rating
Lakeside stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a patio Lakeside
- Rentals with a washing machine and dryer Lakeside
- Rentals with a firepit Lakeside
- House rentals Lakeside
- Rentals with outdoor seating Lakeside
- Family-friendly rentals Lakeside
- Rentals with a fireplace Lakeside
- Pet-friendly rentals Lakeside
- Rentals with pools Clay County
- Rentals with pools Florida
- Rentals with pools United States
- Crescent Beach
- University of Florida
- EverBank Stadium
- St Augustine Amphitheatre
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- Lightner Museum
- Kathryn Abbey Hanna Park
- Fountain of Youth Archaeological Park
- Summer Haven st. Augustine FL
- St Johns Town Center
- Depot Park
- Vilano Beach Fishing Pier
- TPC Sawgrass
- Adventure Landing Jacksonville Beach
- University of North Florida
- Ravine Gardens State Park
- Lochloosa Lake
- Fort Clinch State Park
- Memorial Park
- St. Augustine Alligator Farm Zoological Park
- Huguenot Memorial Park
- Kingsley Plantation
- Little Talbot





