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 favourite

Home in Haines City

4.88 out of 5 average rating, 136 reviews

3 Bedroom Executive with Private Pool near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 15 minutes from LEGOLAND and 25 minutes 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.

Nov. 18 – 25

$224 CAD per night

Guest favourite

Home in Tampa

4.97 out of 5 average rating, 111 reviews

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk. Full kitchen, W/D & Everything you need provided for a NO stress stay!

Dec. 19 – 26

$222 CAD per night

Guest favourite

Guesthouse in Lake Alfred

4.95 out of 5 average rating, 120 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.

Aug. 9 – 16

$141 CAD per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 233 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 ****

Feb. 10 – 17

$143 CAD per night

Guest favourite

Home in Lakeland

4.86 out of 5 average rating, 109 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.

Nov. 15 – 22

$328 CAD per night

Guest favourite

Home in Winter Haven

4.9 out of 5 average rating, 154 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 96 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.

Sep. 25 – Oct. 2

$311 CAD per night

Guest favourite

Guesthouse in Lakeland

4.94 out of 5 average rating, 82 reviews

Beacon Hill Historic District - Cozy Cottage

Welcome to Lakeland! This studio style cottage resides in Lakeland's Historic Beacon Hill Historic District. The guest house is furnished with a queen size bed, stylish high-top table and chairs, kitchenette, and full bath. Amenities include a shared pool, fire pit, and outdoor dining area. Easy access to downtown and all the Historic Districts of Lakeland. Street parking, private entrance, and self check-in. We hope enjoy all Lakeland has to offer!

May 23 – 30

$182 CAD per night

Guest favourite

Guesthouse in Dade City

4.95 out of 5 average rating, 162 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.

May 9 – 16

$103 CAD per night

Guest favourite

Camper/RV in Lakeland

4.94 out of 5 average rating, 163 reviews

Spacious Camper w/Fire Pit & Hot Tub

Our Travel Camper is an adorable retreat equipped with local made amenities. Plenty of space for sleeping and lounging with 1 pop out, a bunk bed, a seriously comfy queen bed, foldout couch 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!

Jul. 3 – 10

$161 CAD per night

Guest favourite

Guesthouse in Auburndale

4.97 out of 5 average rating, 194 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.

Jan. 9 – 16

$128 CAD per night

Guest favourite

Home in Winter Haven

4.98 out of 5 average rating, 99 reviews

Spectacular Waterfront Home in Winter Haven

Have 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. 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest.

Jun. 24 – Jul. 1

$1,197 CAD per night

Guest favourite

Guest suite in Winter Haven

4.96 out of 5 average rating, 258 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Mar. 7 – 14

$174 CAD per night