Osteen holiday rentals

We found 548 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Osteen that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you expect for your stay, including parking and a TV. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Osteen

Showing deals for:11 Dec - 18 Dec

Interior
Marina
Marina
Property grounds
Exceptional
(72 reviews)

Downtown Floating Bungalow Historic Sanford Lake Monroe Marina

Sanford

8% off
AU$1,868
for 7 nights, 1 houseboat
AU$267 per night
includes taxes & fees
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Living area
Property grounds
Interior
Interior
Exceptional
(18 reviews)

Rocket & Nature Lovers! Vintage European Cottage in a lush Florida Setting

Scottsmoor

7% off
AU$1,964
for 7 nights, 1 cottage
AU$281 per night
includes taxes & fees
Rocket & Nature Lovers! Vintage European Cottage in a lush Florida Setting
Private kitchen
Bedroom with queen bed
Living area
Outdoor dining
Exceptional
(9 reviews)

Mira Bella North - 1BR Tiny House in Lake Helen

Lake Helen

8% off
AU$1,174
for 7 nights, 1 cottage
AU$168 per night
includes taxes & fees
Mira Bella North - 1BR Tiny House in Lake Helen
Interior
Fire pit with seating
Interior
Chef’s kitchen w/2 refrigerators, dish washers,sinks,commercial hood &Wolf range
Exceptional
(30 reviews)

Mediterranean/Spanish Estate Home on Lake Sidney

Deltona

7% off
AU$4,821
for 7 nights, 1 home
AU$689 per night
includes taxes & fees
Mediterranean/Spanish Estate Home on Lake Sidney
Marina
Marina
Interior
Private kitchen
Exceptional
(33 reviews)

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

Sanford

8% off
AU$1,522
for 7 nights, 1 houseboat
AU$217 per night
includes taxes & fees
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Plenty of storage for your groceries with condiments provided in fridge
relax on our new saucer hammock
Living area
Master bedroom with en suite bath and king size bed
Exceptional
(8 reviews)

Quiet Lakeside home w/bbq close to Daytona & Sanford

Deltona

6% off
AU$2,108
for 7 nights, 1 home
AU$301 per night
includes taxes & fees
Quiet Lakeside home w/bbq close to Daytona & Sanford
Private kitchen
Room
Living area
Dining
Exceptional
(19 reviews)

Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly

Lake Mary

8% off
AU$3,083
for 7 nights, 1 home
AU$440 per night
includes taxes & fees
Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly
Exterior
Interior
Interior
Room
Wonderful
(19 reviews)

Family friendly home in Sanford

Sanford

7% off
AU$2,039
for 7 nights, 1 home
AU$291 per night
includes taxes & fees
Family friendly home in Sanford
Room
Living area
Private kitchen
Living area
Exceptional
(58 reviews)

Clear Lake Front home near Orlando / Sanford SFB Boombah

Sanford

7% off
AU$2,138
for 7 nights, 1 home
AU$305 per night
includes taxes & fees
Clear Lake Front home near Orlando / Sanford SFB Boombah
Master BR with en-suite Bath with a separate sink area.
Bright and cheery space with water views all around!
Fire pit, gazebo and kayaks, all for your use!
Bright kitchen with a water view!
Exceptional
(11 reviews)

Waterfront Cottage - Your perfect Retreat to Rest and Relax on the River!

New Smyrna Beach

8% off
AU$2,671
for 7 nights, 1 apartment
AU$382 per night
includes taxes & fees
Waterfront Cottage - Your perfect Retreat to Rest and Relax on the River!
Living area
Private kitchen
Exterior
Room
Exceptional
(11 reviews)

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

Oviedo

8% off
AU$2,142
for 7 nights, 1 home
AU$306 per night
includes taxes & fees
2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house
Room
Private kitchen
Games room
Dining
Exceptional
(5 reviews)

The Billiard: super fun home close to downtown with fully-fenced yard

Sanford

20% off
AU$2,437
for 7 nights, 1 home
AU$348 per night
includes taxes & fees
The Billiard: super fun home close to downtown with fully-fenced yard
Dining
Interior
Living area
Private kitchen
Wonderful
(12 reviews)

Charming 2-bedroom house with WiFi, AC in fabulous Deltona , Florida

Deltona

15% off
AU$1,389
for 7 nights, 1 home
AU$198 per night
includes taxes & fees
Charming 2-bedroom house with WiFi, AC in fabulous Deltona , Florida
Room
Private kitchen
Interior
Interior
Exceptional
(39 reviews)

Only 2 blocks from all the action on Canal Street!

New Smyrna Beach

7% off
AU$3,192
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Only 2 blocks from all the action on Canal Street!
Property grounds
Interior
Exterior
Private kitchen
Exceptional
(19 reviews)

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Geneva

7% off
AU$1,117
for 7 nights, 1 home
AU$160 per night
includes taxes & fees
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Interior
Outdoor dining
Private kitchen
Exterior
Exceptional
(20 reviews)

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

Sanford

16% off
AU$2,538
for 7 nights, 1 home
AU$363 per night
includes taxes & fees
Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
Coffee bar/reheat station. Complimentary coffee/tea, creamer and sugar provided.
Make it a classic campfire night at The Sanctuary Den. We’ll curate it for you!
Breakfast bar
Room
Exceptional
(8 reviews)

A Backyard Retreat Worth Finding • Close to Downtown Sanford

Sanford

6% off
AU$1,367
for 7 nights, 1 apartment
AU$195 per night
includes taxes & fees
A Backyard Retreat Worth Finding • Close to Downtown Sanford

  • 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

Scenic Osteen will entice you

Learn about the unique charm of Osteen with a stay in a holiday home rental. Travellers appreciate the kayaking in this scenic city. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Osteen

Do you want to find attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Osteen a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Central Florida Zoo & Botanical Gardens (9.3 mi / 14.9 km)
  • New Smyrna Beach Golf Course (18.4 mi / 29.7 km)
  • Crane Lakes Golf and Country Club (18.8 mi / 30.3 km)
  • Orlando Speedworld (21.4 mi / 34.4 km)
  • Mayfair Country Club (10.5 mi / 16.8 km)
  • Timacuan Golf Club (11.6 mi / 18.6 km)

Exploring the natural landscape of Osteen

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

  • Lake Monroe (6.5 mi / 10.4 km)
  • Lake Jesup (8.8 mi / 14.2 km)
  • Little Big Econ State Forest (11.1 mi / 17.9 km)
  • Black Bear Wilderness Area (11.5 mi / 18.5 km)
  • Central Winds Park (11.6 mi / 18.7 km)
  • Boombah-Soldiers Creek Park (12.5 mi / 20.1 km)

How to get to and around Osteen

The nearest airport is in Orlando, FL (SFB-Orlando Sanford Intl.), located 6.9 mi (11.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Daytona Beach, FL (DAB-Daytona Beach Intl.), which is 24.2 mi (39 km) away.

Frequently asked questions

What is the best area to stay in Osteen when booking a holiday rental?
When considering a holiday rental in Osteen, Florida, a popular area to stay is near the picturesque Lake Ashby. This serene neighbourhood offers a tranquil atmosphere, great for those looking to unwind amidst nature. The area is surrounded by lush greenery and is ideal for outdoor enthusiasts, with opportunities for fishing, boating, and hiking in the nearby parks.Another appealing option is the vicinity of the St. Johns River, which provides stunning views and a variety of recreational activities. This area is not only known for its natural beauty but also for its proximity to attractions such as the Blue Springs State Park, where visitors can enjoy swimming, manatee watching, and leisurely picnics by the river.In terms of holiday rentals, Osteen has a diverse array of properties available, suiting different preferences and budgets. Staying in these inviting neighbourhoods allows visitors to experience both the charm of Osteen and the convenience of accessing nearby attractions in the greater Central Florida area.
What is the most popular type of holiday rental accomodation in Osteen?
In Osteen, holiday houses and cottages are the most popular types of holiday rentals, with several options available throughout the area. These rentals typically provide ample space with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many properties also feature outdoor spaces such as patios or gardens, allowing guests to enjoy the pleasant Florida weather.
Are there any family house rentals in Osteen?
In Osteen, Florida, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious homes that often include amenities such as fully equipped kitchens, large living rooms for family gatherings, and outdoor spaces where kids can play safely. Many properties also come with conveniences like Wi-Fi and air conditioning to ensure a comfortable stay.Visitors can enjoy the nearby scenic beauty of the St. Johns River, superb for outdoor activities like fishing and boating, as well as the natural attractions at the nearby Canova Beach Park.
Can I rent a holiday home with a pool or hot tub in Osteen?
In Osteen, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation and leisure. This charming area, located near the St. Johns River, offers a tranquil setting with the convenience of nearby attractions. Many of the rentals come equipped with private swimming pools, hot tubs, outdoor seating areas, and fully equipped kitchens, providing a comfortable and enjoyable stay for families or groups. Additionally, some properties may include amenities such as barbecue facilities and spacious gardens, allowing guests to fully embrace the outdoor lifestyle.
Are there pet-friendly house rentals in Osteen?
In Osteen, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these rentals come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces, which are superb for relaxing after a day of exploring. Some properties may also feature fenced yards, making them ideal for pets to play safely.The area is close to various parks and nature reserves, providing ample opportunities for outdoor activities with your furry friends. For instance, the nearby Lake Harney Conservation Area offers walking trails and scenic views, allowing for enjoyable outings with pets.
Are there any remote work holiday rentals in Osteen?
In Osteen, Florida, there are several holiday rentals suitable for remote work. These properties typically offer essential amenities such as free Wi-Fi, ensuring a reliable internet connection for those needing to work from home. Many accommodations also feature comfortable living spaces and designated work areas, allowing for a productive environment.Osteen is a charming area, close to the scenic St. Johns River, where you can enjoy outdoor activities during breaks from work. The nearby towns offer local shops and cafes, adding convenience to your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Osteen?
In Osteen, popular holiday rental amenities include spacious balconies and patios, providing guests with lovely outdoor spaces to enjoy the pleasant Florida weather. Many rentals also feature gardens, allowing for a tranquil environment amidst nature. Onsite parking is commonly available, making it convenient for visitors travelling by car.
When is the best time to visit Osteen for a holiday rental?
April is the most popular month to visit Osteen, Florida, as it falls within the peak travel season from February to April. This period attracts visitors seeking warmth and sunshine, making it great for outdoor activities and exploring the natural beauty of the area. The climate during these months is pleasantly warm, with temperatures ranging from 15 to 27 degrees Celsius, ideal for enjoying the many parks and rivers nearby.Osteen offers a variety of attractions, including the scenic Lake Ashby Park, where you can enjoy bird-watching, picnicking, or simply enjoying the serene surroundings. The proximity to the St. Johns River also provides opportunities for kayaking and fishing, suiting those who appreciate adventure and nature.For those looking for a more budget-friendly option, consider visiting in November. While it's outside the peak season, the weather remains mild, and you can enjoy a quieter atmosphere, allowing for a more relaxed exploration of Osteen's charm.
What are the top attractions in Osteen?
In Osteen, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The nearby Lake Ashby offers opportunities for fishing, boating, and picnicking, making it a popular spot for both locals and tourists. The area surrounding the lake is serene, providing a peaceful retreat for nature lovers.For those interested in wildlife, the Black Bear Wilderness Area is a short drive away, featuring numerous hiking trails where you can observe local flora and fauna. This expansive natural area is ideal for trekking and bird-watching, attracting outdoor enthusiasts looking to explore Florida's unique ecosystems.Additionally, the historic town of Sanford, located just a short distance from Osteen, boasts charming shops and restaurants along its picturesque riverfront.
Are all fees included in the Osteen holiday homes prices shown on Stayz?
Stayz 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 Osteen holiday homes with parking?
Stayz offers a wide selection of holiday homes in Osteen 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 Osteen holiday homes?
You can find great discounts on holiday homes in Osteen on Stayz, 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 Osteen holiday home booking on Stayz?
To find Osteen holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Osteen?
A long-stay holiday home in Osteen 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 Stayz?
Stayz'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 Osteen holiday home?
Book your Osteen 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Osteen?
Prices for holiday homes in Osteen 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. Stayz offers something for every taste and budget, from affordable homes in Osteen to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.