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Vacation 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.

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Guest favorite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.87 out of 5 average rating, 592 reviews

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.

Top guest favorite
The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.
Bungalow in College Park
4.98 out of 5 average rating, 129 reviews

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

Top guest favorite
A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 368 reviews

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

Top guest favorite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guesthouse in Lake Cherokee
4.98 out of 5 average rating, 120 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Top guest favorite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guesthouse in Longwood
4.98 out of 5 average rating, 123 reviews

"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.

Top guest favorite
A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.
Home in Longwood
4.96 out of 5 average rating, 106 reviews

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.

Guest favorite
Home in Sanford
4.87 out of 5 average rating, 262 reviews

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!

Top guest favorite
Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.
Guest suite in Oviedo
4.92 out of 5 average rating, 443 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and there is no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge, microwave, TV, Wifi and access to non-heated swimming pool. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

Top guest favorite
A cozy lounge area features a gray sofa and a small dining table with two wooden chairs. A wall with natural wood accents complements a colorful beach-themed art piece. Light streams through a nearby window, enhancing the inviting atmosphere.
Guest suite in Orange City
4.95 out of 5 average rating, 129 reviews

The Hillside Haven Oasis

Enjoy a warm and inviting stay in our beautiful Sanctuary in your own private guest quarters, sweetly dubbed, "The Hillside Haven Oasis" This is an extension of our home, similar to a Mother In Law Suite. Only shared space would be the outdoors and we leave that for your private enjoyment. We created this Oasis with a desire is for our guests to feel calm, comfort and tranquility while being showered with Florida Sun. It would be our privilege to serve you as our guests here. :)

Guest favorite
A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.
Home in Lake Mary
4.9 out of 5 average rating, 272 reviews

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

Guest favorite
A modern kitchen features sleek cabinetry and a large island with bar seating. Unique patterned ceiling tiles complement the granite countertops. A stainless steel refrigerator and double ovens are visible, highlighting a functional yet stylish cooking space.
Home in Lake Mary
4.88 out of 5 average rating, 111 reviews

Markham Woods 4BR Pool Retreat near Attractions

1 camera near the front door for security. Recording 24/7 ANY PARTIES HOSTED WILL BE CANCELED STRICT POLICY Great blend of medieval charm and modern comforts in the spacious living area with expansive glass windows. Luxuriate in the lavish master suite boasting a king-sized bed and indulgent oversized showers. Outside, discover a sprawling backyard with a pool. Conveniently close to Disney, Daytona Beach, and local attractions for a serene getaway. getaway.

Top guest favorite
A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.
Home in Sanford
4.99 out of 5 average rating, 156 reviews

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

Popular amenities for Lake Mary rentals with a pool

When is the best time to visit Lake Mary?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$40,990 GYDG$26,769 GYDG$30,324 GYDG$28,651 GYDG$28,651 GYDG$28,651 GYDG$25,723 GYDG$26,142 GYDG$33,670 GYDG$28,233 GYDG$28,860 GYDG$26,142 GYD
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Quick stats about vacation rentals with a pool in Lake Mary

  • Total vacation rentals

    Explore 30 vacation rentals in Lake Mary

  • Nightly prices starting at

    Lake Mary vacation rentals start at G$4,183 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Lake Mary vacation rentals include wi-fi 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!