Longwood holiday homes

We found 1,297 holiday rentals — enter your dates for availability
Discover a selection of 32 homes and other holiday rentals in Longwood that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and parking. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Longwood

Showing deals for:1 Jan - 8 Jan

Full Kitchen
Living room with sky windows for natural sunlight
Front yard
Back Yard
Exceptional
(6 reviews)

Orlando 1 Acre 4 BD Home Central Near Universal

Orlando

12% off
NZ$4,045
for 7 nights, 1 home
NZ$578 per night
includes taxes & fees
Orlando 1 Acre 4 BD Home Central Near Universal
Fully stocked gourmet kitchen whether a snack or full course meal. It has it all
Living area
Living area
Quiet living room is a great place to relax and unwind. An Oasis for reading!
Exceptional
(77 reviews)

Beautiful 5br 4bath, sleeps 14: Wekiva Springs, Disney, Universal & Antiques.

Apopka

8% off
NZ$6,153
for 7 nights, 1 home
NZ$879 per night
includes taxes & fees
Beautiful 5br 4bath, sleeps 14: Wekiva Springs, Disney, Universal & Antiques.
Outdoor dining
Dining
Living area
Private kitchen
Wonderful
(21 reviews)

Orlando 4 BR Home Centrally Located on Dead End St

Orlando

8% off
NZ$4,155
for 7 nights, 1 home
NZ$594 per night
includes taxes & fees
Orlando 4 BR Home Centrally Located on Dead End St
Property grounds
Terrace/patio
Room
Pool
Exceptional
(115 reviews)

Lake Front Suite -Close to all Attractions

Apopka

8% off
NZ$1,255
for 7 nights, 1 home
NZ$179 per night
includes taxes & fees
Lake Front Suite -Close to all Attractions
Interior
Marina
Marina
Property grounds
Exceptional
(73 reviews)

Downtown Floating Bungalow Historic Sanford Lake Monroe Marina

Sanford

8% off
NZ$2,396
for 7 nights, 1 houseboat
NZ$342 per night
includes taxes & fees
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Living area
Living area
Interior
Private kitchen
Exceptional
(6 reviews)

A comfortable home close to the city, yet tucked away from the noise.

Orlando

7% off
NZ$2,374
for 7 nights, 1 home
NZ$339 per night
includes taxes & fees
A comfortable home close to the city, yet tucked away from the noise.
Private kitchen
Marina
Marina
Exterior
Exceptional
(35 reviews)

Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford

Sanford

8% off
NZ$1,996
for 7 nights, 1 houseboat
NZ$285 per night
includes taxes & fees
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Dining
Room
Private kitchen
Living area
Exceptional
(19 reviews)

Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10

Lake Mary

8% off
NZ$4,679
for 7 nights, 1 home
NZ$668 per night
includes taxes & fees
Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
Interior
Interior
Private kitchen
Room
Wonderful
(19 reviews)

Family friendly home in Sanford

Sanford

7% off
NZ$2,732
for 7 nights, 1 home
NZ$390 per night
includes taxes & fees
Family friendly home in Sanford
Bathroom
Interior
climate control, couch, room, refrigerator, indoor, bed, private space, Large TV
Room
Exceptional
(9 reviews)

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Sanford

14% off
NZ$1,461
for 7 nights, 1 apartment
NZ$209 per night
includes taxes & fees
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Living area
Living area
Have a family game night with Uno, Jenga, Yahtzee, and more!
Room
Exceptional
(23 reviews)

Stylish 2BR in Downtown Orlando, Walk to Lake Eola & Colonial Town!

Orlando

11% off
NZ$2,781
for 7 nights, 1 home
NZ$397 per night
includes taxes & fees
Stylish 2BR in Downtown Orlando, Walk to Lake Eola & Colonial Town!
Exterior
Outdoor dining
Private kitchen
Interior
Exceptional
(20 reviews)

Charming 1920's House - pet friendly, 45 minutes from beach & attractions!

Sanford

16% off
NZ$3,294
for 7 nights, 1 home
NZ$471 per night
includes taxes & fees
Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
only 2 minutes drive to Uptown Mall walk park is beutiful. Mall and Imax movie D
Private kitchen
Entry 🌙
dinning
Exceptional
(70 reviews)

Tiny Hidden Cottage

Longwood

8% off
NZ$1,474
for 7 nights, 1 cottage
NZ$211 per night
includes taxes & fees
Tiny Hidden Cottage
Interior
Property grounds
Room
Private kitchen
Exceptional
(8 reviews)

Trailhouse Retreat with Hot Tub, Firepit & Bikes

Sanford

7% off
NZ$4,082
for 7 nights, 1 home
NZ$583 per night
includes taxes & fees
Trailhouse Retreat with Hot Tub, Firepit & Bikes
private screened swimming pool with sundeck
full size kitchen to utilize everything included
Covered spa/hot tub, patio grill available, view to fenced bach yard
family room directly off the pool patio
Exceptional
(12 reviews)

Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches

Altamonte Springs

7% off
NZ$3,168
for 7 nights, 1 home
NZ$453 per night
includes taxes & fees
Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches
Room
Living area
Living area
Dining
Very good
(8 reviews)

Two bedroom park model near Disney

Apopka

7% off
NZ$1,285
for 7 nights, 1 home
NZ$184 per night
includes taxes & fees
Two bedroom park model near Disney
Living room + TV
Outdoor area
Second Bedroom (with lakeview)
Living Room
Exceptional
(10 reviews)

Charming 2-bedroom lakefront bungalow in Orlando

Orlando

7% off
NZ$1,961
for 7 nights, 1 home
NZ$280 per night
includes taxes & fees
Charming 2-bedroom lakefront bungalow in Orlando
Breakfast bar
Make it a classic campfire night at The Sanctuary Den. We’ll curate it for you!
Room
Coffee bar/reheat station. Complimentary coffee/tea, creamer and sugar provided.
Exceptional
(8 reviews)

A Backyard Retreat Worth Finding • Close to Downtown Sanford

Sanford

6% off
NZ$2,010
for 7 nights, 1 apartment
NZ$287 per night
includes taxes & fees
A Backyard Retreat Worth Finding • Close to Downtown Sanford
Private kitchen
Living area
Dining
Room
Exceptional
(8 reviews)

Cozy Private Apartment 10 minutes from Downtown Orlando

Orlando

7% off
NZ$1,144
for 7 nights, 1 apartment
NZ$163 per night
includes taxes & fees
Cozy Private Apartment 10 minutes from Downtown Orlando
Living area
Interior
Room
Private kitchen
Exceptional
(31 reviews)

Sanford Hideaway • Near Historic Downtown • Sleeps 4 • Free Parking

Sanford

8% off
NZ$1,779
for 7 nights, 1 apartment
NZ$254 per night
includes taxes & fees
Sanford Hideaway • Near Historic Downtown • Sleeps 4 • Free Parking
Living area
Private kitchen
Living area
Room
Exceptional
(12 reviews)

2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house

Oviedo

8% off
NZ$2,706
for 7 nights, 1 home
NZ$387 per night
includes taxes & fees
2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house
Dining
Private kitchen
Room
Interior
Exceptional
(9 reviews)

Charming Walkable Attic Bungalow near Lake Eola with Full Kitchen

Orlando

8% off
NZ$2,343
for 7 nights, 1 apartment
NZ$335 per night
includes taxes & fees
Charming Walkable Attic Bungalow near Lake Eola with Full Kitchen
Room
Living area
Private kitchen
Interior
Exceptional
(18 reviews)

Treehouse Lake Davis - 1BR Private Modern Home with Balcony Downtown

Orlando

8% off
NZ$2,593
for 7 nights, 1 apartment
NZ$370 per night
includes taxes & fees
Treehouse Lake Davis - 1BR Private Modern Home with Balcony Downtown
Dining
Private kitchen
Resident guest greeter, Lightning.
Room
Exceptional
(83 reviews)

Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora

Mount Dora

8% off
NZ$2,908
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Vibrant Longwood will entice you

The lake and surrounding scenery provide a peaceful ambience to your holiday home in Longwood. Well known for its shopping, restaurants and golfing, this cosmopolitan city won't disappoint. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Longwood

Are you hoping to find things to do during your stay? Venture out of your holiday home and experience everything that makes Longwood a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (17.5 mi / 28.2 km)
  • Universal Orlando Resort (17.7 mi / 28.5 km)
  • The Wizarding World of Harry Potter™ (17.4 mi / 28 km)
  • Universal’s Islands of Adventure (17.9 mi / 28.8 km)
  • Universal’s Volcano Bay (18.6 mi / 29.9 km)
  • Central Florida Zoo & Botanical Gardens (8.7 mi / 14 km)

Exploring the natural features in Longwood

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Longwood is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Boombah-Soldiers Creek Park (2.1 mi / 3.3 km)
  • Cranes Roost Park (3.8 mi / 6.2 km)
  • Sanlando Park (3.9 mi / 6.2 km)
  • Central Winds Park (4 mi / 6.5 km)
  • Kraft Azalea Gardens (6.4 mi / 10.3 km)
  • Lake Jesup (7.4 mi / 11.9 km)

How to get to and around Longwood

The nearest airport is in Orlando, FL (SFB-Orlando Sanford Intl.), located 7.6 mi (12.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Orlando International Airport (MCO), which is 18.9 mi (30.4 km) away.

Catch a ride on the metro at Longwood Station for ease of access to the rest of the city.

Frequently asked questions

What is the best area to stay in Longwood when booking a holiday rental?
When considering a holiday rental in Longwood, Florida, the best area to stay in is the charming neighbourhood surrounding the historic downtown. This area boasts a variety of properties, from quaint cottages to more modern homes, providing ample options for visitors. One of the highlights of this neighbourhood is the beautiful Reiter Park, which features walking trails, a playground, and picnic areas, making it a lovely spot for relaxation and outdoor activities. Additionally, the nearby Longwood Historic District offers a fascinating glimpse into the town's past, with its well-preserved architecture and local shops.Another great option is the area near the Wekiva Springs State Park, which is just a short drive away. This natural oasis is great for those who appreciate the outdoors, offering opportunities for swimming, kayaking, and hiking. Staying in this vicinity allows visitors to experience both the tranquillity of nature and the charm of local culture.
What is the most popular type of holiday rental accomodation in Longwood?
In Longwood, holiday houses are the most popular type of holiday rental, with around 104 available across the area. These spacious properties are typically found in family-friendly neighbourhoods and offer various amenities, including fully equipped kitchens, multiple bedrooms, and outdoor spaces such as patios or gardens, making them ideal for families or larger groups. Additionally, there are about 16 cottages which provide a charming, rustic experience, often featuring unique architectural details and cosy interiors. For those seeking smaller accommodations, several apartments, chalets, and condos are also available, suiting different preferences and budgets.
Are there any family house rentals in Longwood?
In Longwood, Florida, there are numerous family-friendly house rentals available—specifically, around 23 options throughout the area. This charming locale is situated near popular attractions such as the scenic Wekiva Springs State Park, which offers opportunities for outdoor activities like hiking and picnicking, making it a great spot for families.Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces ideal for children to play. Additional amenities often include air conditioning and Wi-Fi, ensuring a comfortable stay for all.For families looking to explore, the nearby Cranes Roost Park offers walking trails, playgrounds, and beautiful lakeside views, great for a day out.
Can I rent a holiday home with a pool or hot tub in Longwood?
In Longwood, Florida, there are several holiday homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This suburban area is known for its beautiful parks and proximity to Orlando, making it an ideal spot for families or groups looking to enjoy a relaxing getaway.Travellers can expect a range of amenities in these rentals, including private swimming pools, hot tubs for unwinding, spacious outdoor areas for barbecues, and well-equipped kitchens for preparing meals. Many properties also provide comfortable living spaces, superb for lounging after a day of exploring the local attractions or enjoying the Florida sunshine.
Are there pet-friendly house rentals in Longwood?
In Longwood, there are some pet-friendly house rentals available, offering a variety of amenities for travellers. Many of these homes come equipped with spacious yards, ideal for pets, as well as modern kitchens and comfortable living spaces. Guests can expect features such as private patios, BBQ grills, and Wi-Fi, making them great for both relaxation and entertainment.The area is well-situated near several parks, providing excellent opportunities for outdoor activities with pets. For instance, the nearby Cranes Roost Park offers walking trails and green spaces, making it a great spot for a leisurely stroll with your furry companions. Additionally, the local community often hosts pet-friendly events, adding to the charm of the neighbourhood.
Are there any remote work holiday rentals in Longwood?
In Longwood, Florida, there are numerous remote work holiday rentals available, with around 124 options to choose from. This charming area offers a variety of properties that cater to those needing a comfortable workspace while enjoying a getaway. Many of these rentals come equipped with free Wi-Fi, ensuring that guests can stay connected and productive during their stay.Travellers can expect a mix of amenities such as spacious work areas, fully equipped kitchens for convenient meal preparation, and comfortable living spaces superb for relaxation after a day's work. The surroundings of Longwood also provide access to local parks and recreational areas, making it easy to take breaks and enjoy the outdoors. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Longwood?
In Longwood, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals comfortably. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant Florida weather. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, most rentals come with coffee and tea makers, superb for a refreshing start to the day.
When is the best time to visit Longwood for a holiday rental?
The best time to visit Longwood for a holiday rental is during the peak season from February to April, with March being particularly popular. This vibrant period draws visitors eager to enjoy the pleasant Florida climate and explore the area's beautiful parks and nature trails. Expect comfortable temperatures ranging from 15 to 25 degrees Celsius, superb for outdoor activities such as hiking and sightseeing.During these months, the landscape comes alive, with blooming flowers and lush greenery, making it an ideal time for nature lovers. Longwood's proximity to attractions like the Central Florida Zoo and the historic downtown area enhances the appeal for travellers.For those looking for a more budget-friendly option, November is a wonderful time to visit. While it falls outside the main tourist season, you can still relish the mild weather and enjoy a quieter atmosphere, allowing for a more relaxed experience as you explore local parks and gardens.
What are the top attractions in Longwood?
In Longwood, Florida, visitors can explore several attractions that showcase the area's natural beauty and cultural offerings. One of the most great spots is the historic downtown area, where you can find charming boutiques, local eateries, and the beautiful Reiter Park, which features walking trails, playgrounds, and picnic areas.Another highlight is the nearby Wekiva Springs State Park, known for its stunning springs and diverse wildlife, offering opportunities for canoeing, kayaking, and hiking along scenic trails. The park's natural beauty makes it a great spot for outdoor enthusiasts.For those interested in history, the Longwood Historic District features several preserved buildings that reflect the town's heritage, providing a glimpse into its past.
Are all fees included in the Longwood holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Longwood holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Longwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Longwood holiday homes?
You can find great discounts on holiday homes in Longwood on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Longwood holiday home booking on Bookabach?
To find Longwood holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Longwood?
A long-stay holiday home in Longwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Longwood holiday home?
Book your Longwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Longwood?
Prices for holiday homes in Longwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Longwood to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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