
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!

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.

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.

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 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.

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!

Legoland Lakeside Splash 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.

Full-Service Gated Resort, Disney, Universal, MCO!
Minutes to Theme Parks, Full-Service Resort, Space for the Whole Family, Pools, Splash Pad & Much More! This 3-bedroom villa at Bahama Bay Resort & Spa is ideal for family or group vacations. Comfortable queen beds are standard in the main bedroom and first guest bedroom, while the second guest bedroom features two twin beds. The villa features two full bathrooms. All resort amenities are free and available to guests. 24/7 guard gate and front desk service.

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.

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**

It's too much like a elegant mini-hotel (7)
It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.
Popular amenities for Lakeland rentals with a pool
House rentals with a pool

Hollingsworth Pool Home

Lakeland Paradise Villa

Awesome Vacation Home w/ Private Heated Pool/Spa

Little Castle on the canal on lake Arietta

Florida Oasis w/ Pool near LEGOLAND

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

Fantastic Water Front Home on the Chain of Lakes

Great Location | Heated Pool | Awesome Design
Condo rentals with a pool

9 miles from Disney - Bella Piazza spacious condo

Magical Champions Gate 3/2 Tuscan Penthouse

Stylish Condo 20 mins to Disney/King Bed

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

Spacious Apartment Near Disney

Chic Disney Resort Condo • Pool Access Near Parks

Sol and Mar Resort Style Condo - NO RESORT FEES

"Ocean's Gate" - 2BD/2BA condo near Disney
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

7547oml-Solterra Resort

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Champions Gate 6bed 5bath Vacation Home

The Manors at Westridge Home W/ Private Pool
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.ﺇ529 | ﺩ.ﺇ518 |
| 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 120 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 4,280 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
110 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Saint Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Condo rentals Lakeland
- Villa rentals Lakeland
- Guesthouse rentals Lakeland
- Waterfront rentals Lakeland
- Family-friendly rentals Lakeland
- Cabin rentals Lakeland
- Apartment rentals Lakeland
- Rentals with a patio Lakeland
- Rentals with lake access Lakeland
- Rentals with outdoor seating Lakeland
- Cottage rentals Lakeland
- Smoking-friendly rentals Lakeland
- Rentals with a hot tub Lakeland
- House rentals Lakeland
- Fitness-friendly rentals Lakeland
- Rentals with a washer and dryer Lakeland
- Lakehouse rentals Lakeland
- Pet-friendly rentals Lakeland
- Private suite rentals Lakeland
- Rentals with a fire pit Lakeland
- Rentals with a fireplace Lakeland
- Rentals with pools Polk County
- Rentals with pools Florida
- Rentals with pools United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Raymond James Stadium
- Epcot
- Weeki Wachee Springs
- ESPN Wide World of Sports
- Walt Disney World Resort Golf
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Vinoy Park
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- Jannus Live




