
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.

Unique Concrete House Boat! No cleaning fees!
This ferrocement boat Later Gator 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.

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!

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.

Lake Front Suite -Close to all Attractions
Multi Room Suite on Little Bear Lake - Fun place to stay! The suite is attached to main house but has private entrance. 1/2 bath in Master BR. A Separate Full Luxury Bath w High Flow Therapy Shower provides Spa quality relief from a tough day! Master has King and hideabed, smart tv w Hulu. HEPA air filtrate removes viruses. Wireless internet. Kitchenette has tv, microwave, hot water kettle, coffee pot, toaster oven, charcoal grill (outside), frig/freezer w water, tea, wine & snacks.

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

Bonheur Ala Maison
Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

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.
Popular amenities for Longwood rentals with a pool
House rentals with a pool

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

Lake Dora Dream-Waterfront/Pool

Quiet Place, convenient to everything!

Waterfront Wizarding Near Universal's Harry Potter

4 bedroom Modern pool home, close to UCF&Boombah

Rate Discount~ Pool~Private Country Retreat

The Lemon Cottage -NO EXTRA FEES

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

3161-305 Resort Lake View Disney Universal Orlando

5 mins Universal 10 mins Epic park | Rustic LOFT

303_To Infinity & the Ocean Breeze Apartment

Suites at Lake Buena Vista close Disney Spring A2

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Westgate Palace Resort 2 bedroom
Home rentals with a private pool

Beautiful 9 Br Pool Home In the Solterra Resort!

Gorgeous 9bd (sleeps 24) In the Solterra Resort!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $288 CAD | $289 CAD | $276 CAD | $278 CAD | $281 CAD | $281 CAD | $322 CAD | $306 CAD | $267 CAD | $252 CAD | $292 CAD | $276 CAD |
| 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 $96 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Longwood vacation rentals include wifi 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 Kissimmee
- Epcot
- ESPN Wide World of Sports
- Amway 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




