
Vacation rentals with a pool in Longwood
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longwood
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.

Comfortable Guest Suite-Stylish Altamonte Springs!
Enjoy a stylish experience with *remodeled pool* in this Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

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.

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

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.

"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.

Pvt Fishing lk , Pets,Nature, Pool,garage
No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , 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 DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

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

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.

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.

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 Longwood rentals with a pool
House rentals with a pool

3BR / 2BR Heated Pool Home 7 Min to Disney |

3 BR/2BA Home w Private Pool~12 min to Airport!

Lake Dora Dream-Waterfront/Pool

Quiet Place, convenient to everything!

4 bedroom Modern pool home, close to UCF&Boombah

Rate Discount~ Pool~Private Country Retreat

⭐ Beautiful 4/2, 🏌Golf, 🧡 Pool & 🎮 Games!

Tropical Oasis - Heated Luxury Pool - Game Room
Condo rentals with a pool

Lovely Winter Park Home close to Hospitals !

Stylish Condo 20 mins to Disney/King Bed

Enchanting Newly Renovated 1.5miles to Disney (760

5 mins Universal 10 mins Epic park | Rustic LOFT

Resort Style Sunshine Oasis near Theme Parks

tranquil resort, near Disney, no extra fee.208

Suites at Lake Buena Vista close Disney Spring A2

Sol y Mar Resort Style Condo - NO RESORT FEES
Other vacation rentals with a pool

Entire Condo with Water View.

Pool House Paradise-Walk to Downtown Lake Mary

Sunny Side Stay

“Lakefront” Guesthouse Getaway

Cozy Zen DT Orlando Apartment - Free Parking

Entire cottage for 5, close to Disney, Universal!

Villa with Guest House & Pool-Patio

Generations Gateway (Pool/Sauna)
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ768 | ﺩ.ﺇ771 | ﺩ.ﺇ735 | ﺩ.ﺇ742 | ﺩ.ﺇ749 | ﺩ.ﺇ749 | ﺩ.ﺇ859 | ﺩ.ﺇ815 | ﺩ.ﺇ712 | ﺩ.ﺇ672 | ﺩ.ﺇ779 | ﺩ.ﺇ735 |
| 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 vacation rentals with a pool in Longwood

Total vacation rentals
Explore 20 vacation rentals in Longwood

Nightly prices starting at
Longwood vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 990 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
20 of Longwood vacation rentals include wi-fi access

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

4.9 Average rating
Longwood 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
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town
- Epcot
- ESPN Wide World of Sports
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Daytona International Speedway
- Universal's Volcano Bay
- Playalinda Beach
- Discovery Cove
- Aquatica
- Apollo Beach
- Island H2O Water Park
- Titusville Beach
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club




