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Vacation rentals with a pool in Lakeland

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Lakeland

  • Total vacation rentals

    Explore 150 vacation rentals in Lakeland

  • Nightly prices starting at

    Lakeland vacation rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 5,320 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    140 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!

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
An open living space features a dining area with a floral tablecloth and wooden chairs. Adjacent, a cozy seating area includes a light fixture and a large window providing natural light. The polished tile flooring reflects the warmth of the interior.
Home in Lakeland

Edinger's Nest

Relax with the whole family in this natural setting with abundant birds and wildlife. Host has garden next door with seasonal fruits and vegetables. Located in central Florida between Tampa and Orlando. Easy access to I-4 with a short drive to Disney, Busch Gardens, and Legoland. Directly across the lake from the Detroit Tiger's Stadium with beautiful sunset views and home game Sat. night fireworks. 5 min. drive to Southeastern U. 10 min to Florida Southern U. & 14 min to Florida Polytechnic U.

LocationFamilyLayout

5.0 out of 5 average rating, 63 reviews
Top guest favorite
Home in Cypress Gardens

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)

ValueFamilyOutdoor spaces

4.98 out of 5 average rating, 137 reviews
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

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.

ValueLocationAmenities

4.99 out of 5 average rating, 160 reviews
Top guest favorite
The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.
Home in Winter Haven

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!

ValueFamilyWalkability

4.98 out of 5 average rating, 138 reviews
Guest favorite
A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.
Home in Winter Haven

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!

LocationValueLayout

4.98 out of 5 average rating, 124 reviews
Top guest favorite
Home in Lakeland

“Pool Retreat, Sleeps 10. Near Downtown Lakeland”

Welcome to this beautiful house with a pool in Lakeland, ideal for families and groups of up to 10 guests. Large pool with a covered terrace, lounge chairs and a grill. 3 bedrooms, 6 comfortable beds and 3 full bathrooms. Equipped kitchen, washer and dryer. Fenced garden, perfect for children. Close to downtown, Lake Hollingsworth, and parks. Legoland is 25 minutes away, Tampa is 45 minutes away, and Orlando is 1 hour away. Self check-in, fast Wi-Fi, and EV charger.

LocationValueTV

4.97 out of 5 average rating, 38 reviews
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

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.

LocationFamilyBackyard

4.92 out of 5 average rating, 226 reviews
Top guest favorite
The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.
Home in Winter Haven

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 6 miles from LEGOLAND, this spacious 4BR, 3BA pool home is made for family vacations and group getaways. Spend sunny Florida days relaxing by the private screened pool and patio, then gather together in the bright, open living and dining space. Comfortable beds, a fully equipped kitchen, stylish furnishings and plenty of room to spread out make this an easy, relaxing home base for theme park days, pool time and making memories together in Central Florida.

LocationValueCheckout

4.99 out of 5 average rating, 149 reviews
Top guest favorite
A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.
Home in Winter Haven

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!

LocationFamilyPool

4.98 out of 5 average rating, 125 reviews
Guest favorite
Home in Lakeland

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.

FamilyValueGrill

4.83 out of 5 average rating, 29 reviews
Guest favorite
The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.
Home in Lakeland

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!

FamilyLocationTV

4.85 out of 5 average rating, 40 reviews
Top guest favorite
A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.
Home in Auburndale

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).

LocationValueGrill

4.95 out of 5 average rating, 171 reviews

Popular amenities for Lakeland rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Haines City

Breathtaking Home

FamilyValueHot tub

4.89 out of 5 average rating, 133 reviews
Guest favorite
The screened-in patio area features a spacious pool with clear water, surrounded by a stone deck. Comfortable seating is arranged nearby, providing a relaxing space for lounging. The area is enclosed, offering protection from insects.
Home in Lakeland

Casa Corona Del Mar - With Heated Pool!

FamilyLocationNearby

4.89 out of 5 average rating, 53 reviews
Guest favorite
A spacious living room features two light-colored sofas facing each other, positioned around a central glass-top coffee table. A modern fireplace is visible with a flat-screen TV mounted above it. Large windows and glass doors invite natural light, leading to the outdoor area.
Home in Lakeland

Lakeland Highlands Oasis - 3BR Heated Pool Home

FamilyValueAccuracy

4.87 out of 5 average rating, 61 reviews
Superhost
Home in Lakeland

McQuillen Mansion

FamilyValueHospitality

4.95 out of 5 average rating, 41 reviews
Top guest favorite
Home in Lakeland

Family Heated Pool Home Sleep 12 Near Tampa Disney

FamilyLocationAmenities

5.0 out of 5 average rating, 51 reviews
Guest favorite
The single-story white villa is surrounded by lush green grass and mature trees. Windows are framed with dark accents, and several planters are positioned along the exterior. The expansive yard offers a spacious area for outdoor activities.
Home in Lakeland

Lakeland Paradise Villa

FamilyLocationGrill

4.98 out of 5 average rating, 45 reviews
Guest favorite
A modern kitchen and dining area feature glossy white cabinetry and sleek stainless steel appliances. A large island with three stools provides ample workspace, while a dining table with high-backed chairs accommodates several guests. Natural light streams through the windows, enhancing the bright and open feel.
Home in Lakeland

Beautiful Family Home with a pool

FamilyValueTV

4.91 out of 5 average rating, 54 reviews
Guest favorite
Home in Lakeland

3/2 Luxury Spanish Villa + Pool + Pet Friendly

FamilyLocationParking

4.89 out of 5 average rating, 99 reviews

Condo rentals with a pool

Guest favorite
The exterior features a beige, single-story structure surrounded by lush greenery and palm fronds. Two entry doors are framed by neatly trimmed shrubbery, contributing to a welcoming atmosphere. A clear blue sky is visible overhead, enhancing the bright appearance of the entrance.
Condo in Mulberry

Time Out!

ValueFamilyQuiet

4.88 out of 5 average rating, 114 reviews
Guest favorite
Condo in Davenport

Luxurious living just 15 min/Disney.

LocationFamilyCheckout

4.88 out of 5 average rating, 117 reviews
Guest favorite
Condo in Kissimmee

Green View Condo near Disney

FamilyValueParks

4.84 out of 5 average rating, 108 reviews
Guest favorite
An open-concept living area features a spacious gray sofa with decorative pillows, a coffee table, and a dining set for six. Natural light fills the room through a large window, while a modern ceiling fan provides comfort. The kitchen area, visible in the background, showcases dark cabinetry and pendant lighting.
Condo in Reunion

NEW 3 Bedroom Resort Condo - Disney - Universal

FamilyLocationBeach

4.9 out of 5 average rating, 259 reviews
Top guest favorite
Two thatched-roof cabanas are set on a sandy area, providing shaded spots for relaxation. Lush greenery surrounds the space, and a hammock can be seen hanging nearby. The clear blue sky enhances the tranquil environment.
Condo in Davenport

Bahama Bay Hideaway - Condo by Orlando theme parks

FamilyLocationNearby

4.89 out of 5 average rating, 140 reviews
Guest favorite
A resort-style pool area is surrounded by palm trees and lush landscaping, with inviting lounge chairs arranged nearby. The clear water reflects a bright sky, and a separate lounge area with a decorative façade is partially visible in the background.
Condo in Davenport

Orlando Spacious 2 Suites & Resort-Style Pool

ValueFamilyView

4.85 out of 5 average rating, 185 reviews
Top guest favorite
A spacious outdoor pool area is surrounded by lush palm trees and vibrant landscaping. Lounge chairs are arranged around the pool, which is accented by umbrellas. Cobblestone paving offers a sturdy surface, inviting relaxation in a sunlit setting.
Condo in Davenport

Spacious & Peaceful Condo Near Champions Gate

FamilyLocationCheck-in

4.88 out of 5 average rating, 100 reviews
Guest favorite
A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.
Condo in Kissimmee

Stylish Condo 20 mins to Disney/King Bed

FamilyValueSolo travel

4.87 out of 5 average rating, 148 reviews

Other vacation rentals with a pool

Top guest favorite
Home in Winter Haven

Lakefront Fun: Pool, Games, Hot Tub, Sleeps 17

LocationFamilyGetting around

5.0 out of 5 average rating, 28 reviews
Guest favorite
Home in Lakeland

Horse Haven

FamilyLocationCleanliness

4.88 out of 5 average rating, 26 reviews
Guest favorite
A sparkling pool reflects the clear blue sky, surrounded by a welcoming patio area. Comfortable seating is available under a shaded structure, perfect for relaxation. A BBQ grill can be seen in the background, enhancing the outdoor experience.
Home in Lakeland

Home Paradise Heated Pool Jacuzzi BBQ Backyard

FamilyLocationBackyard

4.87 out of 5 average rating, 95 reviews
Top guest favorite
A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.
Home in Cypress Gardens

Winter Haven Waterfront Retreat

LocationFamilyDecor

5.0 out of 5 average rating, 45 reviews
Top guest favorite
A neatly arranged sleeping area features a black metal frame bed with white bedding. A small nightstand holds a lamp and a framed picture. A decorative plant adds greenery, while dark curtains cover the window, enhancing the cozy ambiance.
Home in Lakeland

Modern Pool House w/ King Beds - 5 min to Downtown

ValueFamilyLong stay

4.97 out of 5 average rating, 97 reviews
Guest favorite
Home in Lakeland

Golden Pearl Oasis {Private Pool & Screened} 3-8ft

FamilyLocationCheck-in

4.88 out of 5 average rating, 16 reviews
Top guest favorite
Home in Lakeland

Spacious Pool Home in South Lakeland

FamilyLocationCondition

4.98 out of 5 average rating, 54 reviews
Superhost
A spacious outdoor pool area is highlighted with a curvy shape and gentle steps leading in. Sun loungers are positioned nearby, inviting relaxation. A well-kept lawn and trees surround the area, adding to the tranquil environment, while a covered patio is visible adjacent to the pool.
Home in Lakeland

Prado Paradise

LocationFamilyIndoor spaces

4.9 out of 5 average rating, 79 reviews

When is the best time to visit Lakeland?

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Avg. price€141€153€154€163€141€141€122€124€122€119€141€145
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