
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.

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.

Couples clothing optional escape hot tub 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.

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. $3800/mo. +taxes - Nov-Feb. Inquire for rate.

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!

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.

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!

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

Downtown HistoricLuxury • Designer Kitchen & Baths

Your Home Away From Home

Private oasis, heated pool, exceeds expectations

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

Pool Home with Game Room in Heart of Jax Beach!

Quiet and Serene House with Heated pool near beach

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

Paradise Palms Estate
Condo rentals with a pool

My HOUSE is your HOUSE

Spanish Colonial Design One Bedroom Condominium

"Gone Coastal" is Steps From the Sand!

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

Jacksonville Beach Front A-Wave-From-It-All!

Beachcomber Oceanfront 180* panoramic view

Gated Sawgrass Beach Club - WALK to BEACH!

Luxury Golf & Spa condo in Beautiful St. Augustine
Other vacation rentals with a pool

Cozy House mins from NAS JAX & Orange Park Mall

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

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

Luxurious one BD king/pool/gym

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

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

The Waddle Inn

Guest Favorite! 8th Floor Luxe King Suite PetOK
When is the best time to visit Lakeside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$39,279 GYD | G$40,114 GYD | G$41,577 GYD | G$41,577 GYD | G$41,577 GYD | G$41,577 GYD | G$46,382 GYD | G$51,815 GYD | G$49,516 GYD | G$35,100 GYD | G$38,443 GYD | G$37,816 GYD |
| 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 G$10,446 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!
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- Rentals with a fireplace Lakeside
- Rentals with a washer and dryer Lakeside
- Rentals with a patio Lakeside
- Family-friendly rentals Lakeside
- Rentals with outdoor seating Lakeside
- Rentals with pools Clay County
- Rentals with pools Florida
- Rentals with pools United States
- EverBank Stadium
- Anastasia State Park
- University of Florida
- Summer Haven st. Augustine FL
- Whetstone Chocolates
- Lightner Museum
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- Depot Park
- Ravine Gardens State Park
- Adventure Landing Jacksonville Beach
- St. Augustine Alligator Farm Zoological Park
- St Augustine Amphitheatre
- Little Talbot
- Florida Museum of Natural History
- Fort Clinch State Park
- Memorial Park
- Autobahn Indoor Speedway & Events - Jacksonville, FL
- Saint Augustine Town Plan Historic District
- TPC Sawgrass
- Friendship Fountain
- San Sebastian Winery
- Museum of Science and History
- St Johns Town Center




