Holiday rentals with a pool in Lakeside

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.

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

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.

Posh Pool and Pond Landing

Welcome to your own private oasis! This home is the perfect escape from the hustle of everyday life. Whether you're looking to enjoy quality time with family, or simply relax in paradise, this house embodies comfort and tranquility. With spacious living areas, charming decor, this home is the ultimate vacation destination. Enjoy the beautiful environment, surrounded by lush tropical foliage - Perfect to soak up the sun, breathe clean natural air, and make unforgettable memories.

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!

Historic Avondale Pool House | Guest Favorite

Escape to a beautifully restored historic home with a private pool in the heart of Avondale. Walk to restaurants, breweries, and boutiques, then unwind by the pool or in the cabana. Ideal for families, couples, and weekend escapes. Please read the house rules and neighborhood description before booking. Exterior Ring cameras monitor the front entrance and driveway only. There are no interior cameras or cameras in private outdoor living areas.

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!

Elegant & Stylish Pool House with Arcade!

Discover the epitome of elegance and modern style at our trendy pool house, nestled in a quiet and picturesque neighborhood. With a design that seamlessly blends chic and cozy elements, this sanctuary is ideal for families or friends seeking a serene getaway. Enhance your experience with a Street Fighter arcade and board games, offering endless entertainment and a touch of nostalgia, perfect for guests of all ages.