Osteen Holiday Rentals

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Check prices for these dates

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Osteen

Terrace/patio
The Front Porch

Apartment in Sanford

3.0 star property
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
The Front Porch
Exterior
The Blue Aztec

Apartment in Sanford

3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Exterior
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Holiday Home in Whispering Oaks

9.2 out of 10, Wonderful, (236)
"Very cute neighborhood. Comfy house. Met our needs, stayed one night before a cruise.Amazing paintings throughout house!Good restaurant nearby."
United States
Stephanie M.
The price is HK$506
HK$897 total
includes taxes & fees
24 Dec - 25 Dec
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Exterior
Totally 80's

Apartment in Sanford

3.0 star property
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is HK$623
HK$1,221 total
includes taxes & fees
14 Dec - 15 Dec
Totally 80's
Terrace/patio
“NATURE IN THE CITY”

Mobile Home in Union Park

2.0 star property
9.0 out of 10, Wonderful, (6)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is HK$596
HK$1,702 total
includes taxes & fees
6 Dec - 7 Dec
“NATURE IN THE CITY”
Living area
Boho Nights

Apartment in Sanford

3.0 star property
8.8 out of 10, Excellent, (6)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Floor plan
Daytona 3BR Getaway Pool, Gym, Pet Friendly

Apartment in Daytona Beach

3.0 star property
The price is HK$710
HK$2,622 total
includes taxes & fees
5 Dec - 6 Dec
Daytona 3BR Getaway Pool, Gym, Pet Friendly
Fridge, microwave, oven, stovetop
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Cottage in Lake Helen

9.8 out of 10, Exceptional, (36)
"A really lovely little property, especially the adorable front porch! I would have appreciated some more kitchen supplies, but aside from that it was a perfect stay!"
United States
Ren Brady P.
The price is HK$701
HK$1,163 total
includes taxes & fees
26 Dec - 27 Dec
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Private kitchen
Charming Caribbean 1-bedroom roomy Apartment in amazing Downtown Sanford

Apartment in Sanford

2.0 star property
9.6 out of 10, Exceptional, (4)
"Clean, close to downtown restaurant and sights. Was a work trip and host helped my wife set up her work computer which was much appreciated. Just a great place to stay for short term."
United States
Frank F.
The price is HK$740
HK$2,240 total
includes taxes & fees
3 Dec - 4 Dec
Charming Caribbean 1-bedroom roomy Apartment in amazing Downtown Sanford
Interior
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Mobile Home in Geneva

9.6 out of 10, Exceptional, (16)
"I stayed in the Luxury RV for the past 3 miles months while I was working nearby. The host, and his family, were excellent hosts and were constantly checking to make sure I had all my needs met. I sincerely hope that I can return to stay again in the future!"
United States
Aaron A.
The price is HK$748
HK$1,298 total
includes taxes & fees
3 Dec - 4 Dec
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Outdoor pool
The Little Lake Mary Guest House • Warm, Cozy & Inviting

Cottage in Lake Mary

9.8 out of 10, Exceptional, (43)
"Absolutely incredible house, felt like home away from home"
United States
Hannah R.
The price is HK$876
HK$2,094 total
includes taxes & fees
13 Dec - 14 Dec
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Exterior
The Jazz Loft

Apartment in Sanford

3.0 star property
7.6 out of 10, Good, (5)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
The Jazz Loft
Property grounds
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

Apartment in Deltona

2.0 star property
9.6 out of 10, Exceptional, (4)
"Loved the proximity to the wonderful bike and walking trail!"
United States
Sharon H.
The price is HK$662
HK$2,272 total
includes taxes & fees
8 Dec - 9 Dec
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
Interior
To The Moon at Titusville/Space Coast/

Holiday Home in Titusville

9.2 out of 10, Wonderful, (31)
"Nice property close to restaurants and activities. Patio was really nice. Enclosed so no bugs. A few minutes walk to the park where we watched a SpaceX launch. Host was very attentive and friendly. Definitely would stay there again. "
United States
Kelly N.
The price is HK$763
HK$1,870 total
includes taxes & fees
3 Dec - 4 Dec
To The Moon at Titusville/Space Coast/
Microwave, oven, stovetop
Vacation Mode: Activated in NSB

Apartment in Canal Street Historic District

10.0 out of 10, Exceptional, (2)
"Great location. Charming. Very responsive host. "
United States
Gary H.
The price is HK$554
HK$1,217 total
includes taxes & fees
3 Dec - 4 Dec
Vacation Mode: Activated in NSB
2 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Apartment in Orlando

10.0 out of 10, Exceptional, (5)
"Great host, and stayed connected with us."
United States
Christopher
The price is HK$817
HK$1,959 total
includes taxes & fees
10 Dec - 11 Dec
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Exterior
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Holiday Home in Deltona

9.6 out of 10, Exceptional, (10)
"The space was private, comfortable and very clean. Ashlee is an amazing hostess. "
United States
Belinda M.
The price is HK$610
HK$1,105 total
includes taxes & fees
9 Dec - 10 Dec
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Exterior
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Apartment in Orlando

10.0 out of 10, Exceptional, (27)
"This was an excellent place to stay. Perfect for a couple. The entire place was extremely clean and very welcoming. We would absolutely stay here again. "
United States
Craig K.
The price is HK$662
HK$1,426 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Private Apartment - Stylish & Spotless — No sharing areas
1 bedroom, desk, iron/ironing board, free WiFi
Yania's Cozy Getaway

Apartment in Azalea Park

9.6 out of 10, Exceptional, (11)
"Clean quiet property. Perfect for studying. "
United States
Angela S.
The price is HK$476
HK$1,305 total
includes taxes & fees
3 Dec - 4 Dec
Yania's Cozy Getaway
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House

Cottage in Sanford

8.8 out of 10, Excellent, (13)
"Cozy little place to stay"
United States
Ruth P.
The price is HK$416
HK$1,101 total
includes taxes & fees
14 Dec - 15 Dec
The Sanford Foodie Guest House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osteen Hotel Reviews

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

10/10 Excellent
"Super friendly and helpful front desk clerk! Room was ok, bathroom wasn’t the cleanest but not a huge deal. Slept great!"
Daniel 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Orlando Lake Mary

Find out more about Osteen

Search for holiday rentals in Osteen on Expedia! You can easily find your home rentals, villas, holiday apartments in Osteen using one of the methods below:

  • View our selection of featured holiday rentals in Osteen
  • Use the map to find apartments and other holiday homes in the Osteen neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osteen while they last

Look no further and take a look at our great range of rental properties in Osteen!

Frequently asked questions

Can I find holiday rentals in Osteen?

Yes, there are holiday rentals in Osteen close to Pell's Citrus & Nursery, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osteen has to offer?

Pirates Cove Resort Studios: This holiday home rental outside of Osteen is on the beach, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave and kitchenware.

How many holiday rentals are there in Osteen?

Expedia has 3 holiday rentals for your stay in Osteen.

What’s there to see and do in Osteen?

Lake Jesup and Lake Monroe Conservation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Pell's Citrus & Nursery. Lake Jesup Conservation Area and Lake Ashby Park are other places to visit while you're in town.

What’s a holiday rental in Osteen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osteen. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.