Osteen Holiday Rentals

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Holiday Rentals in Osteen

Our top choices for Osteen holiday rentals

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
9.8 out of 10, Exceptional, (12)
"Everything was great"
Intercoastal Retreat

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (248)
"Our family had a great vacation this place was perfect for our family of 6"
New Smyrna Waves by Exploria Resorts

Shoreline Suites & Cabana Cottages

2.0 star property
8.8 out of 10, Excellent, (378)
"Love the location and how cute the cabanas are. "
The price is AU$180
includes taxes & fees
2 Sept - 3 Sept
Shoreline Suites & Cabana Cottages

Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

9.6 out of 10, Exceptional, (262)
"On the beach and a short walk away from Flagler Ave."
Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

Fantasy Island Resort, Daytona Beach Shores

4.0 star property
8.6 out of 10, Excellent, (106)
"The people there were very generous and made the stay there very pleasant!!"
The price is AU$228
includes taxes & fees
28 Sept - 29 Sept
Fantasy Island Resort, Daytona Beach Shores

Pirates Cove Resort Studios

3.0 star property
6.2 out of 10, (139)
"Clean and comfortable"
The price is AU$227
includes taxes & fees
2 Sept - 3 Sept
Pirates Cove Resort Studios

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 AU$211
includes taxes & fees
2 Sept - 3 Sept
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

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 AU$691
includes taxes & fees
8 Sept - 9 Sept
Spacious 5-bedroom house South Daytona with Movie room, Hot tub & Gameroom

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 AU$204
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 Reef # 311 Right On The Beach! Breathtaking Views All Around!

9.8 out of 10, Exceptional, (232)
"Loved the location and had a great weekend stay. Place was very nice and clean"
Ocean Reef # 311 Right On The Beach! Breathtaking Views All Around!

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 "
Oceanside Inn Studios by Brightwild

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 AU$283
includes taxes & fees
9 Sept - 10 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!

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

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 AU$439
includes taxes & fees
10 Sept - 11 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, (60)
"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 AU$752
includes taxes & fees
10 Sept - 11 Sept
Beautiful Beach Front Condo
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

Find out more about Osteen

Find out more about Osteen

Everything you need to know about Osteen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osteen holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osteen holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osteen. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osteen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osteen holiday rentals we have selected for you start as low as AU$180 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osteen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osteen holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osteen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.