
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 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.

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.

Historic Designer Home • Luxury Baths • Steps2DWTN
Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

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.

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!

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.

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.

Private Pool Getaway • 5 min Beach • Sleeps 9

Private Pool Home • Quiet • Near Beaches & Dining

Zen Flamingo: Poolside Peace Near Beaches and TPC

Pool Home with Game Room in Heart of Jax Beach!

San Marco Home • Pool, Hot Tub, Grill

Clear-Roof Heated Pool • Luxury All-Season Swim
Condo rentals with a pool

Mi CASA es su CASA

Spanish Colonial Design One Bedroom Condominium

Ocean Front Gem: Top Floor Corner Unit

Ocean front Beachside Bliss

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

Oceanfront Oasis: Top Floor Paradise

Newly renovated! Steps to BEACH & POOL!

Beachcomber Oceanfront 180* panoramic view
Other vacation rentals with a pool

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

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

Mid-century Modern Pool Paradise 🌴 📸 🔥

Rest, relax, revive-lovely 1 bedroom cabin

3BR Cottage w/Private Pool & Fenced Yard - Dogs OK

King Bed•Salt Pool•Luxe 1BR •Gym• Super Clean Vibe

Cottage on River

Fun, New Apartment Near NAS 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.ﺇ720 | ﺩ.ﺇ760 | 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 1,030 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 fire pit Lakeside
- Rentals with a fireplace Lakeside
- Pet-friendly rentals Lakeside
- House rentals Lakeside
- Family-friendly rentals Lakeside
- Rentals with a washer and dryer Lakeside
- Rentals with a patio Lakeside
- Rentals with outdoor seating Lakeside
- Rentals with pools Clay County
- Rentals with pools Florida
- Rentals with pools United States
- Crescent Beach
- EverBank Stadium
- University of Florida
- 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
- Whetstone Chocolates
- Adventure Landing Jacksonville Beach
- Ravine Gardens State Park
- University of North Florida
- Lochloosa Lake
- Fort Clinch State Park
- Memorial Park
- St. Augustine Alligator Farm Zoological Park
- Little Talbot
- Florida Museum of Natural History





