
Holiday rentals with a pool in Lake Mary
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lake Mary
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

Relaxing 3-Bedroom Pool Getaway
This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Cozy at Flamingo Cottage
This 3 bedroom, 1.5 bath is equipped for a peaceful stay! At the intersection of 429, I-4 & SR417, under 40 miles from Disney & Parks, close to shopping & transportation, a screened private pool, a backyard, 2-car garage, cable, wi-fi, new appliances, fully equipped, renovated kitchen, a washer and dryer. Inside, tile floors keep allergens at bay. An older home set up to be comfy and homey. Vacation in a home setting! With outdoor seating and citrus trees, Florida is at your doorstep!

⭐ Beautiful 4/2, 🏌Golf, 🧡 Pool & 🎮 Games!
Enjoy the best of FL! Make this charming & relaxing home in Sanford the home base for your next great vacation! Centrally located close to stores, malls, Lake Mary Sports Complex (1.9 miles) & Trailblazer park. A community pool within walking distance & Mayfair Golf Course right across the street (0.8 miles)! 45 min. to beaches, 40 to Disney, 35 to Universal, I-Drive shopping, 30 to Winter Park, & 20 to the Springs. This beautiful home has all the amenities you'd expect and then some!

Stylish & spa like Getaway - peaceful garden suite
Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Gated community XL pool Home 2500sq/f
Our LK Mary home sits in Between the 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost

Enjoy the Magic - Floating Cottage on the River
Welcome to FLOATING COTTAGE . . . Imagine staying in a small cottage, gently afloat on the beautiful St. Johns River in Sanford, Florida. Perfect for social distancing! Sanitized between guests. Contactless check-in. Floating Cottage provides a magical space to relax, refresh and explore. Relax on the front porch; enjoy the warm breeze while watching marina activity, and the bounty of nature. Enjoy the peaceful comfort of the fully equipped small home.

Lovely Winter Park Home close to Hospitals !
Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

The Cypress House
This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb

Private 4-Bedroom home with pool!
Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!
Popular amenities for Lake Mary rentals with a pool
House rentals with a pool

Private pool home near Downtown

Bonheur Ala Maison

Manor on Knottingham Near Disney

Modern Tropical House Heated Salt Pool

Luxury Vacay Home w/ Pool 5Br/5Bath near Disney

The Lemon Cottage -NO EXTRA FEES

Spacious Home with Pool & Hot Tub near Downtown

Stunning Orlando Getaway w/Spa & Heated Pool
Apartment rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

NUEVO APTO CON PARQUE DE AGUA Y CERCA DE DISNEY

Maria Luz Studio-Huge Terrace/Universal area.

VCR2-108 Deluxe New Apartment - Convention Center

Modern Lake view Condo 1 mile from Disney

The Point Hotel & Suites - 705H Luxury - Pool View

Luxury Studio, Near to Universal-Epic ,And Disney!

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

3/2 near beaches and theme parks

Pool House Paradise-Walk to Downtown Lake Mary

LaLa's Carriage House

Quiet Neighborhood in the Country

Beautiful cozy private studio !!

Kyle's Place - Private Unit, Pool + Laundry Room

Lake Front Suite -Close to all Attractions

Sanford 2bd 2bth pool Airpt BeachTrain Orlando 8pp
When is the best time to visit Lake Mary?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $248 SGD | $162 SGD | $183 SGD | $173 SGD | $173 SGD | $173 SGD | $155 SGD | $158 SGD | $204 SGD | $220 SGD | $236 SGD | $244 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about holiday rentals with a pool in Lake Mary

Total holiday rentals
Explore 30 holiday rentals in Lake Mary

Nightly prices starting at
Lake Mary holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Lake Mary holiday rentals include wifi access

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

4.9 Average rating
Lake Mary 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
- Universal's Volcano Bay
- Give Kids the World Village
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Playalinda Beach
- Aquatica
- Disney's Hollywood Studios
- Camping World Stadium
- ICON Park
- Island H2O Live!




