Vacation rentals with a pool in Lakeland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lakeland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Winter Haven

4.99 out of 5 average rating, 114 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers two bedrooms, a loft , full kitchen and laundry and one full bathroom. The 1100 square foot space which offers 12 foot ceilings and unique interior design will leave you amazed. If your looking for more than a space to sleep but a place to vacation than this is It.

Guest favorite

Guesthouse in Lake Alfred

4.96 out of 5 average rating, 148 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Guest favorite

Home in Auburndale

5 out of 5 average rating, 102 reviews

Private Pool Tropical Garden Oasis, Fenced Yard

Come stay @ "The EstablishMint" while you experience Central Florida! Professionally designed home close to Disney, Legoland, Golf Courses, Lake Myrtle Sports Complex, Winter Haven Chain of Lakes, Waterskiing, Bike Trails. Between Tampa & Orlando. Minutes from Lakeland. Come relax at this clean, modern home. Hang out in the private pool or play yard games. Family & pet-friendly with fenced back yard. Walking distance to Lake Juliana for great fishing and watersports! Extended stays welcome!

Guest favorite

Home in Haines City

4.89 out of 5 average rating, 157 reviews

Southern Dunes Villa - Pool - Golf - near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 13 miles from LEGOLAND and 22 miles from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

Guest favorite

Guesthouse in Winter Haven

4.87 out of 5 average rating, 254 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Superhost

Home in Lakeland

4.84 out of 5 average rating, 140 reviews

Hollingsworth Pool Home

This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

Guest favorite

Villa in Haines City

4.82 out of 5 average rating, 117 reviews

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

Guest favorite

Guesthouse in Dade City

4.94 out of 5 average rating, 181 reviews

Hickory Breeze Guest House

We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.

Guest favorite

Guesthouse in Orlando

5 out of 5 average rating, 226 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Superhost

Guesthouse in Lakeland

4.87 out of 5 average rating, 106 reviews

Luxury Cottage on Prestigious Million$ Property

Close to everything. Away from it all. Situated on 5 grassy acres and home to the Lewman family, this pristine south Lakeland home is fully fenced with a gated entry. The Guest House sits detached next to the main house with plenty of shared parking. Enjoy the outside without the worry of traffic. Free Wifi. We pride ourselves in providing a clean and safe home for you to make your own while you are here.

Guest favorite

Camper/RV in Lakeland

4.94 out of 5 average rating, 187 reviews

Spacious Camper w/Fire Pit,Hot Tub,Pool

Our Travel Camper is an adorable retreat equipped with local made amenities. Plenty of space for sleeping and lounging with 1 small fold out sofa , a large bunk bed, a seriously comfy queen bed, and table/bed. Private bathroom, full kitchen, grill, Wi-Fi, TV, with a fire pit in our secluded shaded Oak back yard with access to our screened in pool( seasonal use) The Keurig machine is a morning necessity!

Guest favorite

Guesthouse in Auburndale

4.98 out of 5 average rating, 217 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.