
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.

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 home—fully equipped kitchen, baths, workspace, washer and dryer, WiFi, cable TV, and dining area. A heated community pool is available. The neighborhood has no through traffic—ideal for walking or running. Nearby are shopping and eating establishments, Lakeland-Linder airport, Publix headquarters, and I-4 for travel to Tampa or Orlando.

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.

Hollingsworth Pool Home
This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

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.

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

Luxury Cottage on Prestigious Million$ Property
Close to everything. Away from it all. Situated on 5 grassy acres and home to the Lewman family, this pristine south Lakeland home is fully fenced with a gated entry. The Guest House sits detached next to the main house with plenty of shared parking. Enjoy the outside without the worry of traffic. Free Wifi. We pride ourselves in providing a clean and safe home for you to make your own while you are here.

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.

Legoland Getaway 7 mins • Sleeps 7 • Elevator
Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.
Popular amenities for Lakeland rentals with a pool
House rentals with a pool

Relax in Heated Saltwater Pool w/ Screened Lanai

Spacious 4BR Home w/ King Bed+Covered Pool

Beautiful Villa/Golf Retreat between Orlando&Tampa

3 bedroom Villa in Kissimmee

Heated Pool Home 4BD/2BA Sleep12 Near Disney-Tampa

Florida Oasis w/ Pool near LEGOLAND

Winter Villa in Florida by the Lakes

Lifes A Beach at Southern Dunes
Condo rentals with a pool

Magical Champions Gate 3/2 Tuscan Penthouse

Stylish Condo 20 mins to Disney/King Bed

Disney Oasis by the lake

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

Spacious Apartment Near Disney

Themed Resort Condo | Pool | Spa | Mins to Disney

Disney & Epic Free Shuttle, Kitchen

Lakefront Resort Condo near Disney & Universal
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

115ep- West Haven

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

416bc-West Haven

The Manors at Westridge Home W/ Private Pool
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 $42 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 guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Weeki Wachee Springs
- Raymond James Stadium
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Vinoy Park
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- Jannus Live