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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Osteen

Tropical Suites at Sunglow Resort

4.5 star property
8.8 out of 10, Excellent, (53)
"The front door need to change new door please. Thank you "
Tropical Suites at Sunglow Resort

Intercoastal Retreat

3.0 star property
9.6 out of 10, Exceptional, (9)
"Really nice"
Intercoastal Retreat

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (247)
"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

4.0 star property
8.6 out of 10, Excellent, (105)
"The studio Apt. Was excellent but the let out couch bed was not comfortable at all & as a guest me & my wife had to make our own bed & take out the trash as guest that’s not expected of us to do"
The price is NZ$253
includes taxes & fees
21 Sept - 22 Sept
Fantasy Island Resort, Daytona Beach Shores

Shoreline Suites & Cabana Cottages

2.0 star property
8.8 out of 10, Excellent, (376)
"Love the location and how cute the cabanas are. "
The price is NZ$241
includes taxes & fees
24 Aug - 25 Aug
Shoreline Suites & Cabana Cottages

Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

9.6 out of 10, Exceptional, (261)
"Had a wonderful time on our extended weekend. The property was wonderful, we are definitely planning to return. Beautiful views from the balcony and easy access to the beach and the night life on Flagler Ave. We give it 5 stars."
Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

Pirates Cove Resort Studios

3.0 star property
6.2 out of 10, (138)
"Nice clean room with great water view!"
The price is NZ$267
includes taxes & fees
24 Aug - 25 Aug
Pirates Cove Resort Studios

Spacious 5-bedroom house South Daytona with Movie room, Hot tub & Gameroom

9.0 out of 10, Wonderful, (2)
"Perfectly located gorgeous getaway house..."
The price is NZ$764
includes taxes & fees
1 Sept - 2 Sept
Spacious 5-bedroom house South Daytona with Movie room, Hot tub & Gameroom

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

9.2 out of 10, Wonderful, (220)
"Nice place to stay when waiting to board ship. "
The price is NZ$263
includes taxes & fees
25 Aug - 26 Aug
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

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 NZ$240
includes taxes & fees
3 Sept - 4 Sept
Castaways Resort Studios

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

Ocean Front Condo - Sea Turtle Penthouse Breathtaking View -Walk to Flagler Ave

10.0 out of 10, Exceptional, (57)
"Our stay at Sea Turtle was most enjoyable. The view of the beach and ocean is breathtaking. The condo is charmingly decorated, well maintained and communication with the owner was excellent. The king-size bed is very comfortable, and thoughtful little details throughout made our stay completely comfortable. We fell in love with the town of New Smyrna Beach and the surrounding area. Can't wait to go back!"
Ocean Front Condo - Sea Turtle Penthouse Breathtaking View -Walk to Flagler Ave

Oceanside Inn Studios by Brightwild

3.5 star property
6.0 out of 10, (1)
"I like itvwas right on beach "
The price is NZ$615
includes taxes & fees
27 Aug - 28 Aug
Oceanside Inn Studios by Brightwild

Lake Front Suite -Close to all Attractions

9.4 out of 10, Exceptional, (80)
"The property was amazing. Would definitely stay there again !"
Lake Front Suite -Close to all Attractions

The House On Crawford COTTAGE Historic House, Independent Apartment

9.4 out of 10, Exceptional, (101)
"This was the perfect spot for 2 out of town friends to enjoy this beautiful beach town. Quaint, cozy, comfy and quiet. Ideal location! Just lovely. "
The price is NZ$310
includes taxes & fees
4 Sept - 5 Sept
The House On Crawford COTTAGE Historic House, Independent Apartment

BEACHFRONT NEWLY remodeled 4 bed/4 Bath 1/2 Block from the Main strip & shops!

8.4 out of 10, Very good, (82)
"Check in easy , property extremely accessible, great host , clean house, coming back next year !!!"
BEACHFRONT NEWLY remodeled 4 bed/4 Bath 1/2 Block from the Main strip & shops!

Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out

9.0 out of 10, Wonderful, (20)
"Access and location to beach was fantastic. Property very clean and equipped. "
The price is NZ$494
includes taxes & fees
3 Sept - 4 Sept
Beachfront Property, Near Flagler Ave, Early Check in - Late Check Out

Sea Club IV

3.0 star property
8.6 out of 10, Excellent, (59)
"Very nice accommodations will use again "
Sea Club IV

Beautiful Beach Front Condo

9.8 out of 10, Exceptional, (113)
"Had a great view, was cozy and is located at a great beach!"
The price is NZ$827
includes taxes & fees
2 Sept - 3 Sept
Beautiful Beach Front Condo

Silver Beach Club

3.5 star property
8.4 out of 10, Very good, (68)
"This was a nice hotel, staff was great! "
The price is NZ$276
includes taxes & fees
31 Aug - 1 Sept
Silver Beach Club
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

Top Osteen Hotel Reviews

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.