Osteen Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Osteen

Tropical Suites at Sunglow Resort
Relax by the clear pool overlooking the ocean, surrounded by sun loungers and a beachside building.

Tropical Suites at Sunglow Resort

4.5 star property
8.6 out of 10, Excellent, (52)
"Clean, easy, family friend! Will definitely be coming back often to stay! So happy i found this place! "
The price is S$434
includes taxes & fees
11 Aug - 12 Aug
Tropical Suites at Sunglow Resort
New Smyrna Waves by Exploria Resorts
Enjoy a serene beach experience with access to the ocean.

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (244)
"Our family had a great vacation this place was perfect for our family of 6"
New Smyrna Waves by Exploria Resorts
Fantasy Island Resort, Daytona Beach Shores
Beach/ocean view

Fantasy Island Resort, Daytona Beach Shores

4.0 star property
8.6 out of 10, Excellent, (104)
"The people there were very generous and made the stay there very pleasant!!"
The price is S$212
includes taxes & fees
7 Sept - 8 Sept
Fantasy Island Resort, Daytona Beach Shores
Silver Beach Club
Park your vehicle and enjoy the beachside views.

Silver Beach Club

3.5 star property
8.4 out of 10, Very good, (68)
"Not a good location."
The price is S$187
includes taxes & fees
4 Sept - 5 Sept
Silver Beach Club
Castaways Resort Studios
Enjoy stunning ocean views from the comfort of our hotel, surrounded by lush lawns and palm trees.

Castaways Resort Studios

3.0 star property
5.8 out of 10, (83)
"Loved the ocean view from the room-great access to beach thru security door-great hot water shower pressure-comfortable beds-tv had Netflix-great location to dining"
The price is S$170
includes taxes & fees
13 Aug - 14 Aug
Castaways Resort Studios
Shoreline Suites & Cabana Cottages
Relax by the pool surrounded by sun loungers and a palm tree, with a scenic ocean view and shaded areas nearby.

Shoreline Suites & Cabana Cottages

2.0 star property
8.8 out of 10, Excellent, (375)
"Love the location and how cute the cabanas are. "
Shoreline Suites & Cabana Cottages
Pirates Cove Resort Studios
Enjoy beach access and safety with a lifeguard tower nearby.

Pirates Cove Resort Studios

3.0 star property
6.2 out of 10, (138)
"Nice clean room with great water view!"
The price is S$179
includes taxes & fees
13 Aug - 14 Aug
Pirates Cove Resort Studios
Vacation Villas
Efficient kitchen with a refrigerator, microwave, dishwasher, sink, and coffee maker.

Vacation Villas

3.0 star property
8.8 out of 10, Excellent, (317)
"We loved our stay here. The staff was amazing. The accommodations weren’t the ritz but we thought they were great for our family and the price. Reminded us of the condo where we used to live in Florida. Quiet neighborhood. Great spot down the road to watch the rocket launches! And overall just a great stay. "
Vacation Villas
Oceanside Inn Studios by Brightwild
Relax by the oceanfront pool surrounded by lounge chairs and a palm tree.

Oceanside Inn Studios by Brightwild

3.5 star property
6.0 out of 10, (1)
"I like itvwas right on beach "
The price is S$424
includes taxes & fees
10 Aug - 11 Aug
Oceanside Inn Studios by Brightwild
Oceanfront Daytona Beach Studio w/ Pool Access
Interior

Oceanfront Daytona Beach Studio w/ Pool Access

3.0 star property
4.0 out of 10, (1)
"Not 100% update in room microwave broken unsafe glass on door and room not 100% clean as should be 1 bed looks like slept in with out washing sheets. bed not made just slop together and must be from a yard sale way outdated for the price per night. freezer frost makes unusable may need to thaw? yes not a question just a fact. Does not even come close to as described at time of booking. "
Oceanfront Daytona Beach Studio w/ Pool Access
Spacious Modern King bed Game Room More
Room

Spacious Modern King bed Game Room More

2.0 star property
Spacious Modern King bed Game Room More
Sea Club IV
Relax by the oceanfront pool surrounded by lounge chairs and umbrellas, with access to the beach and stunning views.

Sea Club IV

3.0 star property
8.6 out of 10, Excellent, (58)
"Very nice accommodations will use again "
Sea Club IV
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osteen Hotel Reviews

Nautilus Inn

Nautilus Inn

10/10 Excellent
"Beautiful room with a beautiful view"
Cheyenne 1-night trip
Posted 18 hours ago
Nautilus Inn

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 a coffee maker.

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.