
Holiday rentals in Longwood
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Longwood

Total holiday rentals
Explore 90 holiday rentals in Longwood

Nightly prices starting at
Longwood holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 4,530 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Longwood holiday rentals include wifi access

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

4.8 Average rating
Longwood stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated holiday rentals in Longwood
Guests agree: these stays are highly rated for location, cleanliness and more.

Farmhouse-Chic Retreat with a Charming Patio
Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches
Your Tropical Paradise is ready and fully furnished from top to bottom! The Pool area has a hot tub. Near all attractions. Top of the line furnishings. Split plan--Master Bedroom is a king suite, pvt bathroom, 2 seperate bdrms on the other side of house. Heated pool/ hot tub has an small add'l fee Moments from I-4 & 20-25 minutes to Disney, Sea World, Universal, Famous Names discount malls, 35 minutes to Daytona & New Symerna Beach. Cranes Roost Park, Altamonte Uptown/Mall, 5 min

Private Studio King Bed & Massage Chair + Sofabed
Quiet, peaceful & centrally-located private studio in Altamonte Springs. 1st floor, 2 private entrances, full kitchen, private AC, strong WiFi, free parking, and total privacy. Walk to Sandlando Park & Seminole Wekiva Trail. Just 2 blocks from I-4, 1.5 mi to Cranes Roost, Uptown & Altamonte Mall. Less than 10 min to Downtown Orlando, Wekiva Springs, hospitals & shopping. Ideal for remote work, extended stays, couples or solo travelers. Enjoy comfort, location & convenience. Book now and enjoy!

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

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

A Home Where Eclectic Luxury Meets Affordability
Welcome to The Altamonte House. Your home away from home. We offer fully free amenities, luxury bedding and pillows, and quintessential design throughout the rooms and home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Pet Fee's per pet: $100 (notify host if you are bringing a pet- charged separately upon check in) Read the rules of the property before booking, to ensure that you agree.

Private 4-Bedroom home with pool!
Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! (Family visits are welcome 🤗) Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!

Sunset Cottage in Lake Mary, Florida
Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

3/1 house conveniently located in central Florida!
Relax with your whole family in this peaceful quiet home. Your home away from home is Conveniently Located close to all the attraction and beaches. It's a small 800 sq ft 3 bed 1 bath House with Casper beds and flat screen in every room. 10 Minutes away from the Altamonte Springs hospital. Full Stocked kitchen with everything you need to cook a home cooked meal. It's a perfect place to stay with your family instead of a Hotel for a more comfortable stay and peace of mind.

Markham Woods 4BR Pool Retreat near Attractions
1 camera near the front door for security. Recording 24/7. Small pre-approved gatherings/events may be allowed with written approval before booking. Max 30 people on property. Event/visitor fee: $20 per person. No outside music after 11 PM. No bottles or glass near the pool. Spacious 4BR Lake Mary retreat with pool, bright living areas, king master suite, oversized showers, and easy access to Disney, Daytona Beach, and local attractions.

RemodeledHouse w/king beds near Downtown Lake Mary
Newly remodeled house located in beautiful Lake Mary, Florida. If the dates don't work for you, see our other nearby listing here: airbnb.com/h/gm-vacation-rentals-2 With the Central Florida theme parks, the surrounding restaurants, Florida's beautiful beaches, and dozens of other nearby attractions, you'll never run out of things to do. We look forward to being able to give you an amazing guest experience at our house.
Popular amenities for Longwood holiday rentals
Other great holiday rentals in Longwood

Casa Alma Vacation Home Steps from LM Event Center

The Tiny Cottage in the Springs/ Central FL

Pool House Paradise-Walk to Downtown Lake Mary

Central Florida Pool Home

2BR Home in Heart of Longwood

Nob Hill-Comfort cozy home away from home Longwood

Cozy & Bright Historic Bungalow

The Lakefront Brantley House
When is the best time to visit Longwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 SGD | $190 SGD | $189 SGD | $162 SGD | $170 SGD | $161 SGD | $161 SGD | $197 SGD | $176 SGD | $166 SGD | $175 SGD | $181 SGD |
| 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Longwood?
Longwood has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Longwood?
Experience the best of Longwood with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Longwood?
Four-legged friends are welcome in Longwood. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Longwood?
Yes! Work meets play with ease at over 40 vacation rentals in Longwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Longwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Longwood, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Longwood have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Longwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Longwood have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Longwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Longwood have wifi?
Absolutely! We offer over 70 house rentals with wifi in Longwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Longwood have free parking?
Absolutely! We offer over 70 house rentals with free parking in Longwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Longwood?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a kitchen, over 70 homes with free parking, over 70 homes with air conditioning, over 70 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Daytona International Speedway
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- Playalinda Beach
- Aquatica
- ICON Park
- Tinker Field





