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.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Guest suite in Longwood

4.97 out of 5 average rating, 109 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. 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 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

Top guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 360 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

Home in Longwood

4.96 out of 5 average rating, 137 reviews

Pvt Fishing lk , Pets,Nature, Pool,garage

No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes and kayak, peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions NEW SHOWS at DISNEY close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Top guest favorite

Guest suite in Oviedo

4.92 out of 5 average rating, 414 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 guests have complete privacy. There are 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. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

Guest favorite

Home in Sanford

4.87 out of 5 average rating, 247 reviews

Private Pool 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

Home in Maitland

4.95 out of 5 average rating, 168 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Superhost

Boat in Sanford

4.91 out of 5 average rating, 317 reviews

Unique Concrete House Boat!!! NO CLEANING FEES!!!

This ferrocement boat was made in Sweden in 1973. That’s right! It’s made of concrete! The boat circumnavigated the globe twice before eventually ending up here in sunny Sanford FL. We spent 2 years completely renovating everything and tried to leave as much of the boat’s original personality intact while adding modern amenities. Restaurant/bar, pool, laundry facilities, showers and restrooms, diner, and marina store all on site, and downtown historic Sanford and river walk close by.

Top guest favorite

Guest suite in Lake Mary

4.96 out of 5 average rating, 344 reviews

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.

Top guest favorite

Guest suite in Orange City

4.94 out of 5 average rating, 114 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. :)

Superhost

Home in Lake Mary

4.89 out of 5 average rating, 262 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

Top guest favorite

Guesthouse in Orlando

4.99 out of 5 average rating, 157 reviews

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

Top guest favorite

Houseboat in Sanford

4.98 out of 5 average rating, 192 reviews

Floating Cottage - Summer/Fall Rates Reduced

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.