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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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Top guest favorite
A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.
Apartment in Winter Haven
4.98 out of 5 average rating, 163 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

Guest favorite
The exterior of the home features a light-colored facade with a welcoming entrance. A neatly landscaped yard includes vibrant green shrubs and a palm tree. The driveway leads to a single-car garage with a white door, set against a backdrop of clear blue skies.
Home in Haines City
4.9 out of 5 average rating, 192 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. 13 miles from LEGOLAND, 22 miles from DISNEY, 29 miles from UNIVERSAL, 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 & the security & beauty of its homes.

Top guest favorite
The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.
Tiny home in Lakeland
4.99 out of 5 average rating, 128 reviews

Charming Tiny House on 5 acres with POOL/ HOT TUB

Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

Guest favorite
A screened-in patio area features a private pool surrounded by comfortable lounge chairs. The inviting water reflects the colors of the sunset sky, and a small dining table is visible nearby. The home is designed for relaxation and outdoor enjoyment.
Villa in Davenport
4.9 out of 5 average rating, 190 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

This sunny single story home has 4 beautiful bedrooms (2 master suites) and 3 full bathrooms with its own private screened pool. It is an ideal accommodation for 2 families to share, or one large family. This villa is located in the gated community, a small peaceful community set away from any main road traffic. The home is situated approximately 15 minutes from the Walt Disney World, and is conveniently located from all major Orlando attractions, nearby restaurants and shopping.

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 138 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Guest favorite
The image presents a collage featuring a private pool area with a screened enclosure under a blue sky, a cozy bedroom with green accents and a whimsical theme, and an elegant living space with modern furnishings. Natural light brightens each area, showcasing inviting design elements.
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Great Location | Heated Pool | Awesome Design

Welcome to Casa Bahama, an inviting and attractive vacation home situated in a peaceful, centrally located gated community. Our spacious property is designed to provide you with a comfortable and memorable stay, allowing you to unwind and appreciate all that the surrounding area has to offer! Our prime location puts you just minutes from a range of popular attractions, including all of the Disney Attractions. • 12 Miles to Old Town • 21 Miles to Universal Studios

Top guest favorite
An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.
Home in Winter Haven
4.91 out of 5 average rating, 199 reviews

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.

Guest favorite
A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.
Villa in Haines City
4.86 out of 5 average rating, 166 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.

Top guest favorite
A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.
Guesthouse in Auburndale
4.97 out of 5 average rating, 245 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. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Top guest favorite
A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.
Villa in Davenport
4.92 out of 5 average rating, 126 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Guest favorite
Townhouse in Lakeland
4.88 out of 5 average rating, 209 reviews

TRENDY TOWNHOME *Btw beach & Disney+ smart TVs*

The BEST home and BEST service in the state of Florida. Modern, trendy townhome right off highway I-4 between Disney and Gulf Beaches! 3 bed, 2.5 bath townhome. 3 smart Tv’s to make your vacation that much more relaxing. And newly renovated kitchen, stocked with every appliance for short or long term stays. You won't find a better place in lakeland whether you are hosting a couples getaway, traveling for work, or vacationing with your family!

Guest favorite
The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.
Condo in Four Corners
4.88 out of 5 average rating, 173 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

Popular amenities for Lakeland rentals with a pool

When is the best time to visit Lakeland?

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Avg. priceﺩ.ﺇ525ﺩ.ﺇ547ﺩ.ﺇ547ﺩ.ﺇ551ﺩ.ﺇ529ﺩ.ﺇ503ﺩ.ﺇ510ﺩ.ﺇ518ﺩ.ﺇ510ﺩ.ﺇ496ﺩ.ﺇ588ﺩ.ﺇ606
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Quick stats about vacation rentals with a pool in Lakeland

  • Total vacation rentals

    Explore 130 vacation rentals in Lakeland

  • Nightly prices starting at

    Lakeland vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 4,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Lakeland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeland rentals

  • 4.9 Average rating

    Lakeland stays are highly rated by guests—averaging 4.9 out of 5!

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