Osteen holiday homes

We found 546 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:4 Dec - 11 Dec

Interior
Marina
Marina
Exterior
Exceptional
(72 reviews)

Downtown Floating Bungalow Historic Sanford Lake Monroe Marina

Sanford

8% off
NZ$2,270
for 7 nights, 1 houseboat
NZ$324 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
NZ$2,355
for 7 nights, 1 cottage
NZ$336 per night
includes taxes & fees
Rocket & Nature Lovers! Vintage European Cottage in a lush Florida Setting
Open floor plan with kitchen/ dining/ family room
Fire pit with seating
Interior
Interior
Exceptional
(30 reviews)

Mediterranean/Spanish Estate Home on Lake Sidney

Deltona

8% off
NZ$5,856
for 7 nights, 1 home
NZ$837 per night
includes taxes & fees
Mediterranean/Spanish Estate Home on Lake Sidney
Marina
Marina
Private kitchen
Exterior
Exceptional
(33 reviews)

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

Sanford

8% off
NZ$1,890
for 7 nights, 1 houseboat
NZ$270 per night
includes taxes & fees
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Living area
Bedroom with queen bed
Private kitchen
Property grounds
Exceptional
(9 reviews)

Mira Bella North - 1BR Tiny House in Lake Helen

Lake Helen

8% off
NZ$1,451
for 7 nights, 1 cottage
NZ$207 per night
includes taxes & fees
Mira Bella North - 1BR Tiny House in Lake Helen
Private kitchen
Room
Living area
Living area
Exceptional
(19 reviews)

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

Lake Mary

8% off
NZ$3,710
for 7 nights, 1 home
NZ$530 per night
includes taxes & fees
Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly
Property grounds
Terrace/patio
Private kitchen
Marina
Exceptional
(53 reviews)

1 Bedroom - 2 Guests Maximum

Oak Hill

8% off
NZ$1,492
for 7 nights, 1 cabin
NZ$213 per night
includes taxes & fees
1 Bedroom - 2 Guests Maximum
Private kitchen
Interior
Exterior
Interior
Excellent
(18 reviews)

Family friendly home in Sanford

Sanford

7% off
NZ$2,478
for 7 nights, 1 home
NZ$354 per night
includes taxes & fees
Family friendly home in Sanford
Exterior
Private kitchen
Room
Living area
Exceptional
(11 reviews)

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

Oviedo

8% off
NZ$2,614
for 7 nights, 1 home
NZ$373 per night
includes taxes & fees
2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house
Interior
relax on our new saucer hammock
Living area
Plenty of storage for your groceries with condiments provided in fridge
Exceptional
(8 reviews)

Quiet Lakeside home w/bbq close to Daytona & Sanford

Deltona

6% off
NZ$2,526
for 7 nights, 1 home
NZ$361 per night
includes taxes & fees
Quiet Lakeside home w/bbq close to Daytona & Sanford
Room
Living area
Private kitchen
Dining
Exceptional
(58 reviews)

Clear Lake Front home near Orlando / Sanford SFB Boombah

Sanford

7% off
NZ$2,598
for 7 nights, 1 home
NZ$371 per night
includes taxes & fees
Clear Lake Front home near Orlando / Sanford SFB Boombah
Exterior detail
Interior
Dining
Private kitchen
Wonderful
(12 reviews)

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

Deltona

15% off
NZ$1,698
for 7 nights, 1 home
NZ$243 per night
includes taxes & fees
Charming 2-bedroom house with WiFi, AC in fabulous Deltona , Florida
Games room
Private kitchen
Interior
Dining
Exceptional
(5 reviews)

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

Sanford

20% off
NZ$2,917
for 7 nights, 1 home
NZ$417 per night
includes taxes & fees
The Billiard: super fun home close to downtown with fully-fenced yard
Fire pit, gazebo and kayaks, all for your use!
Bright and cheery space with water views all around!
Bright kitchen with a water view!
En-Suite Bath with separate sink area and large closet.
Exceptional
(11 reviews)

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

New Smyrna Beach

8% off
NZ$3,224
for 7 nights, 1 apartment
NZ$461 per night
includes taxes & fees
Waterfront Cottage - Your perfect Retreat to Rest and Relax on the River!
Property grounds
Interior
Private kitchen
Exterior
Exceptional
(19 reviews)

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

Geneva

7% off
NZ$1,380
for 7 nights, 1 home
NZ$197 per night
includes taxes & fees
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Exterior
Outdoor dining
Interior
Private kitchen
Exceptional
(20 reviews)

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

Sanford

16% off
NZ$3,120
for 7 nights, 1 home
NZ$446 per night
includes taxes & fees
Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
Living area
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
(7 reviews)

A Backyard Retreat Worth Finding • Close to Downtown Sanford

Sanford

6% off
NZ$1,723
for 7 nights, 1 apartment
NZ$246 per night
includes taxes & fees
A Backyard Retreat Worth Finding • Close to Downtown Sanford
Terrace/patio
Private kitchen
Interior
Room
Exceptional
(39 reviews)

Only 2 blocks from all the action on Canal Street!

New Smyrna Beach

7% off
NZ$3,651
for 7 nights, 1 home
NZ$522 per night
includes taxes & fees
Only 2 blocks from all the action on Canal Street!
Living area
Private kitchen
Room
Dining
Exceptional
(52 reviews)

Hot Tub, Fire Pit, Near the Beach!

Edgewater

8% off
NZ$2,856
for 7 nights, 1 home
NZ$408 per night
includes taxes & fees
Hot Tub, Fire Pit, Near the Beach!
Living area
View from Master
Exterior
Outdoor dining
Exceptional
(134 reviews)

Alderwood lake house Sanford/Orlando near SFB

Sanford

7% off
NZ$2,636
for 7 nights, 1 home
NZ$377 per night
includes taxes & fees
Alderwood lake house Sanford/Orlando near SFB
  • 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)
  • Venetian Bay Golf Club (14.9 mi / 24 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)
  • Twin Rivers Golf Course (13.9 mi / 22.4 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)
  • Lake Monroe Park (9.6 mi / 15.5 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 most popular type of holiday home accommodation in Osteen?
The most in-demand types of holiday homes in Osteen are houses. Prefer something different? Bookabach offers a variety of options to match the needs of our guests, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Osteen?
The average price for a holiday home in Osteen depends on several factors, like length of stay, property type and season. Whether you're dreaming about a sprawling villa with a pool or a comfy cabin that's perfect for two, just add your travel dates to see stays with terrific value.
How much does it cost to rent a beach house in Osteen?
Prices for beach houses in Osteen may differ depending on the size and type of the property and time of year you're travelling. Simply enter your travel dates into Bookabach and how many guests to view your holiday home options and prices. From there you can use our filter tool to tailor your search by ratings, amenities, nearby activities and more.
What are popular home amenities in Osteen?
When it comes to home amenities that people are looking for in Osteen, a barbecue grill, a garden and a nearby waterfront rank highest. With Bookabach holiday homes, there are options to fit your style and taste, whether you're going on a holiday with family, friends or even pets.
What are the top attractions for families in Osteen?
You'll find loads of cool things to see and do with the family in Osteen, such as:
  • AMF Deltona Lanes
  • Gemini Springs Park
  • Green Springs Park
How old do you have to be to rent a holiday home in Osteen?
We advise checking with the Osteen holiday home you'd like on Bookabach as the age limit differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Osteen for?
The length of time you can rent a holiday home in Osteen differs according to the property. Simply enter your desired dates to see a list of options offering extended stays. With lots of features like air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to find the perfect place to call your home away from home in Osteen.