
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.

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!

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.

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.

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.

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!

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

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.

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.

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.

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**

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!

"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
House rentals with a pool

3BR Family Home near Orlando!

Relax in Heated Saltwater Pool w/ Screened Lanai

Disney Area 3BR Pool Home | Family-Friendly

Nature Lover's Lake & Pool Home w/ Sunrise View!

Fantastic Water Front Home on the Chain of Lakes

Disney & Universal Retreat| Heated Pool | Fire Pit

Spacious 4BR Retreat Minutes to Downtown & Airport

3/2 Luxury Spanish Villa + Pool + Pet Friendly
Condo rentals with a pool

Magical Champions Gate 3/2 Tuscan Penthouse

Stylish Condo 20 mins to Disney/King Bed

tranquil resort, near Disney, no extra fee.208

Private Rooftop Suite! No resort fees!

Spacious Apartment Near Disney

Chic Disney Resort Condo • Pool Access Near Parks

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

Orlando Fun: Minutes to Disney and Margaritaville
Other vacation rentals with a pool

Costa 1BD Lake Condo | Paradise | Full Kitchen |

Luxurious Living 15 minutes from Disney.

2309 4BD - Brand New Townhome in Solara Resort

Paradise Cottage & Tiki Hut at Bay Lake Resort

Heron Haven Comfy 2BR condo w/pool Great Location

Kid-friendly Home w/ Pool & BBQ

Little Castle on the canal on lake Arietta

Serenity House|Pool, Gym, & Park
When is the best time to visit Lakeland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ525 | ﺩ.ﺇ547 | ﺩ.ﺇ547 | ﺩ.ﺇ551 | ﺩ.ﺇ529 | ﺩ.ﺇ503 | ﺩ.ﺇ510 | ﺩ.ﺇ518 | ﺩ.ﺇ510 | ﺩ.ﺇ496 | ﺩ.ﺇ588 | ﺩ.ﺇ606 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Raymond James Stadium
- Universal's Volcano Bay
- Give Kids the World Village
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Vinoy Park
- Amalie Arena
- Aquatica
- Disney's Hollywood Studios




