
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.

ā¤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney
Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

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.

Time Out!
Quiet and well appointed, Time Out! Is not a punishment, but a place to relax, regroup, and refresh. Spacious and comfortable, it has all the amenities of a homeāfully equipped kitchen, baths, workspace, washer and dryer, WiFi, cable TV, and dining area. A heated community pool is available. The neighborhood has no through trafficāideal for walking or running. Nearby are shopping and eating establishments, Lakeland-Linder airport, Publix headquarters, and I-4 for travel to Tampa or Orlando.

Near Disney/Kid-Friendly/Disney-Themed/Water Park
Your magical vacation starts here! Just 15 minutes from Disney World, this beautiful, family-friendly home offers luxury, themed rooms, and fun, perfect for creating unforgettable memories. The home is located in the ChampionsGate area. It has 3 bedrooms, 2.5 bathrooms, modern furniture, and super fast internet. You will have free access to the Enclaves at Festival amenities center which features a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant, and gym.

Adorable Agave Suite w/ private pool and entrance
Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your āshomeā 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 ā 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!

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.

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!

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.

Villa Blanca
Relax with the whole family at this peaceful pool home located off the quiet roads along the higher elevation of the Florida ridge. Propane tank for home generator. In ground pool covered by enclosed screen. Property fronts the old Sun Air Golf course (not active). An active bar and grill still operates in the old country club at the end of the neighborhood. Right in the center of both Legoland and Disney World
Popular amenities for Lakeland rentals with a pool
House rentals with a pool

Relax in Heated Saltwater Pool w/ Screened Lanai

Hollingsworth Pool Home

The Bentley Lakehouse

Mickey's Lakefront Villa at Sunset Lakes

Modern Home for Family and Vacations groups

Awesome Vacation Home w/ Private Heated Pool/Spa

*Luxurious Paradise Mansion: Pool, Spa & Cinema

Casa Corona Del Mar - With Heated Pool!
Condo rentals with a pool

Stylish Condo 20 mins to Disney/King Bed

303_To Infinity & the Ocean Breeze Apartment

Suites at Lake Buena Vista close Disney Spring A2

Spacious Apartment Near Disney

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

Lakefront Resort Condo near Disney and Universal

Full-Service Gated Resort, Disney, Universal, MCO!

Close to Disney and Retail Therapy
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Cozy Family Friendly Pool Home with Game Room

The Manors at Westridge Home W/ Private Pool

Balmoral Resort-195 cubic meters
When is the best time to visit Lakeland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $198 CAD | $206 CAD | $206 CAD | $208 CAD | $199 CAD | $190 CAD | $192 CAD | $195 CAD | $192 CAD | $187 CAD | $199 CAD | $195 CAD |
| 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 $42Ā CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
110 of Lakeland vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lakeland rentals

4.9 Average rating
Lakeland stays are highly rated by guestsāaveraging 4.9 out of 5!
Destinations to explore
- SeminoleĀ Vacation rentals
- Central FloridaĀ Vacation rentals
- MiamiĀ Vacation rentals
- Saint Johns RiverĀ Vacation rentals
- OrlandoĀ Vacation rentals
- Gold CoastĀ Vacation rentals
- Miami BeachĀ Vacation rentals
- Fort LauderdaleĀ Vacation rentals
- Four CornersĀ Vacation rentals
- TampaĀ Vacation rentals
- KissimmeeĀ Vacation rentals
- Key WestĀ Vacation rentals
- Rentals with outdoor seatingĀ Lakeland
- Rentals with a hot tubĀ Lakeland
- Private suite rentalsĀ Lakeland
- Rentals with a firepitĀ Lakeland
- Fitness-friendly rentalsĀ Lakeland
- Rentals with a washer and dryerĀ Lakeland
- Waterfront rentalsĀ Lakeland
- Cabin rentalsĀ Lakeland
- Condo rentalsĀ Lakeland
- Smoking-friendly rentalsĀ Lakeland
- Apartment rentalsĀ Lakeland
- Rentals with a patioĀ Lakeland
- Guesthouse rentalsĀ Lakeland
- Rentals with lake accessĀ Lakeland
- Pet-friendly rentalsĀ Lakeland
- Lake house rentalsĀ Lakeland
- Villa rentalsĀ Lakeland
- House rentalsĀ Lakeland
- Family-friendly rentalsĀ Lakeland
- Cottage rentalsĀ Lakeland
- Rentals with a fireplaceĀ Lakeland
- Rentals with poolsĀ Polk County
- Rentals with poolsĀ Florida
- Rentals with poolsĀ United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Raymond James Stadium
- Old Town Kissimmee
- Epcot
- ESPN Wide World of Sports
- Weeki Wachee Springs
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Vinoy Park
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park




