
Holiday 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.

Orlando Poolside Oasis
Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

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

"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!

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

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

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disny

3 bedroom Villa in Kissimmee

Private pool home near Downtown

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Cozy at Flamingo Cottage

The Lemon Cottage -NO EXTRA FEES
Apartment rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

3161-305 Condo Resort Water Park Pools near Disney

NUEVO APTO CON PARQUE DE AGUA Y CERCA DE DISNEY

5 mins Universal 10 mins Epic park | Rustic LOFT

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

Lakefront Resort Studio -5 min to Universal

Maria Luz Studio-Huge Terrace/Universal area.

Stunning view, near Disney.
Other holiday rentals with a pool

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

LaLa's Carriage House

“Lakefront” Guesthouse Getaway

Sapphire Cottage - sleeps 6, on 5 acres with canal

Enjoy the Magic - Floating Cottage on the River

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

Modern efficiency ~ Great location

Lakefront House ~ Pool ~ 5 Star Location
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £155 | £156 | £149 | £150 | £152 | £152 | £174 | £165 | £144 | £137 | £144 | £151 |
| 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 Longwood

Total holiday rentals
Explore 20 holiday rentals in Longwood

Nightly prices starting at
Longwood holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 1,070 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
20 of Longwood holiday 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Rentals with a patio Longwood
- House rentals Longwood
- Rentals with outdoor seating Longwood
- Rentals with a washing machine and dryer Longwood
- Rentals with a firepit Longwood
- Rentals with a fireplace Longwood
- Family-friendly rentals Longwood
- Pet-friendly rentals Longwood
- Rentals with pools Seminole County
- Rentals with pools Florida
- Rentals with pools United States
- 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!




