Vacation rentals with a pool in Lakeland

Adult-Only Retreat w/ Pool & Spa | 18+, Private

🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Family · Value · View

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Location · Value · Pets

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Family · Value · Beach

Legoland Lakehouse Canoe&Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Value · Location · Wifi

McQuillen Mansion

Beautiful Polk county mansion! Bring the whole family to this great place with lots of room for fun. This 5 bedroom 4 bathroom house is centrally located in Lakeland, FL. Close to Tampa and Orlando, this house is perfect for the family get away. Includes bunk bed and a crib. Pool, fire pit, outdoor kitchen and lighted putting green make this the perfect place to unwind and enjoy nature at its finest. The listing is for the house and pool area only.

Family · Location · Long stay

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Location · Value · Breakfast

Casa Planta Cozy Tropical Oasis Pool View Suite

Casa Planta is a garden-inspired oasis where nature & relaxation meet. Our tropical landscape is currently in a seasonal restoration phase due to extreme winter freezes, w/ an evolving garden setting. Enjoy a peaceful walk to your private entrance & unwind poolside in your 2BR/1BA suite. The pool and interior remain exactly as pictured—private, comfy, & serene. The guest suite is attached to the main house but completely blocked off from it.

Location · Value · Backyard

Welcome to your home away from home!

Enjoy a refreshing dip in the private pool or unwind in the serene outdoor space, perfect for soaking up the Florida sun. The separate office space is great for remote work or studying, ensuring you can balance productivity with leisure. We pride ourselves on being kid and pet friendly, making it easy for everyone to feel at home. Located near local attractions, parks, and dining options, you'll have everything you need at your fingertips.

Location · Family · Nearby

“Relaxing Pool Retreat Near Downtown Lakeland”

Welcome to this beautiful and spacious house located near Downtown Lakeland, a few minutes from Lake Hollingsworth. Near Hollis Garden next to Munn Park, Bonnet Spring Park. Near Polk Theater, Legoland 25 min, Tampa Airport 45 min, Orlando theme parks 1 hour. Walking distance from 92 W, 98 Nt and I 4 Fully equipped kitchen, pool, covered terrace and large garden secured and fully fenced for the safety of your pets and children

Family · Location · Quiet

Relax in Heated Saltwater Pool w/ Screened Lanai

Experience luxury and comfort in this spacious rental featuring a master suite with king bed and en suite bath, fully equipped kitchen, dedicated office, and cozy living areas. Enjoy a heated saltwater pool, outdoor TV, grill, and large fenced yard. All bedrooms have large beds, TVs, and ample storage. Includes free WiFi, private driveway, and welcome snacks. Perfect for families, couples, or business travelers!

Location · Family · Laundry

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing. The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

Location · Value · River

Luxury Pool Retreat | Heated Pool & Pet Friendly

You won't find another Lakeland vacation home like this one! The "Landing on Lunn" is a Pet Friendly home that will not disappoint! From the moment you enter the private electronic gate, you will be spoiled with space, sparkling chandeliers, an open floor plan, a gourmet kitchen, spacious bedrooms, and a spa master bath that you won't want to leave!

Family · Location · Parking