Osteen Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Osteen holiday rentals

Living area

Condo resort in Coronado Beach

Ocean Beach Club
2.5 star property
10.0 out of 10, Exceptional, (1 review)
"Great spot, clean room, would love to stay again. "
United States
james
The price is HK$1,298
HK$2,240 total
includes taxes & fees
21 Jan - 22 Jan
Ocean Beach Club
Terrace/patio

Holiday Home in Whispering Oaks

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
9.2 out of 10, Wonderful, (245 reviews)
"We had a pleasant and comfortable stay. This cost less than a night at a Country Inn and Suites we were looking at but we all got our own bedroom. The beds were comfortable. I would definitely stay at this house again if in the area."
United States
Sherry
The price is HK$526
HK$920 total
includes taxes & fees
26 Jan - 27 Jan
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Outdoor pool

Cottage in Lake Mary

The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (46 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is HK$877
HK$2,090 total
includes taxes & fees
27 Jan - 28 Jan
The Little Lake Mary Guest House • Warm, Cozy & Inviting
2 bedrooms, desk, free WiFi

Apartment in Sanford

The Front Porch
3.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"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
Living area

Apartment in Sanford

Boho Nights
3.0 star property
9.2 out of 10, Wonderful, (9 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Living area

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Interior

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"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$624
HK$1,223 total
includes taxes & fees
21 Jan - 22 Jan
Totally 80's
1 bedroom, desk, iron/ironing board, free WiFi

Apartment in Orlando

Clean Luxury Boho in Orlando 25 min from Theme Parks
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The room was beautifully decorated and SPOTLESS. Just what we needed. Close to the airport and highways. Highly recommend."
United States
Leslie
The price is HK$538
HK$1,542 total
includes taxes & fees
26 Jan - 27 Jan
Clean Luxury Boho in Orlando 25 min from Theme Parks
Exterior

Cottage in Lake Helen

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
9.8 out of 10, Exceptional, (36 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is HK$702
HK$1,165 total
includes taxes & fees
21 Jan - 22 Jan
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Interior

Mobile Home in Geneva

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
9.6 out of 10, Exceptional, (16 reviews)
"This place was perfect for me and my dad and my son to stay at while my son played ball close by."
United States
Kevin D.
The price is HK$772
HK$1,326 total
includes taxes & fees
5 Feb - 6 Feb
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Fridge, microwave, oven, stovetop

Mobile Home in Union Park

“NATURE IN THE CITY”
2.0 star property
9.0 out of 10, Wonderful, (6 reviews)
" 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$1,727 total
includes taxes & fees
21 Jan - 22 Jan
“NATURE IN THE CITY”
Property grounds

Aparthotel in Daytona Beach

Silver Beach Club
3.0 star property
8.6 out of 10, Excellent, (76 reviews)
"Staff was very nice. "
United States
Heather
The price is HK$807
HK$908 total
includes taxes & fees
2 Feb - 3 Feb
Silver Beach Club
Beach

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (62 reviews)
"It was a good area to stay "
United States
Christanah O.
The price is HK$616
HK$1,195 total
includes taxes & fees
28 Jan - 29 Jan
Tiny Hidden Cottage
Property grounds

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is HK$1,107
HK$2,732 total
includes taxes & fees
14 Feb - 15 Feb
Incredible Private Lakefront Cottage Retreat
Outdoor dining

Apartment in Casselberry

Traveler's Dream: Refresh & Recharge Poolside
2.0 star property
9.2 out of 10, Wonderful, (7 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
The price is HK$526
HK$1,095 total
includes taxes & fees
27 Jan - 28 Jan
Traveler's Dream: Refresh & Recharge Poolside
Outdoor dining

Holiday Home in Titusville

To The Moon at Titusville/Space Coast/
9.2 out of 10, Wonderful, (31 reviews)
"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$764
HK$1,880 total
includes taxes & fees
26 Jan - 27 Jan
To The Moon at Titusville/Space Coast/
Smart TV

Holiday Home in Deltona

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
9.6 out of 10, Exceptional, (11 reviews)
"Great stay! "
United States
Ash L.
The price is HK$610
HK$1,106 total
includes taxes & fees
2 Feb - 3 Feb
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Interior

Cottage in Port Orange

7 Mi to Beach! Poolside Oasis in Port Orange
3.0 star property
7 Mi to Beach! Poolside Oasis in Port Orange
Exterior

Apartment in Sanford

The Jazz Loft
3.0 star property
8.0 out of 10, Very good, (6 reviews)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
The Jazz Loft
Marina

Apartment in Orlando

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
9.2 out of 10, Wonderful, (13 reviews)
"I stayed at the property from Oct 31st to Nov 2nd for the weekend. This is a very cozy and clean studio apartment which was perfect fo myself and my 2 dogs. There is a fenced in yard at lights at night so my dogs really enjoyed it also. "
United States
michael
The price is HK$577
HK$1,312 total
includes taxes & fees
26 Jan - 27 Jan
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
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

Nautilus Inn

Nautilus Inn

10/10 Excellent
"Beautiful room, clean, nicely appointed, gorgeous view, great deck. Will return. "
Elena 7-night trip
Posted 20 hours ago
Nautilus Inn

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
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  • 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 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.