Osteen Holiday Rentals

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Holiday Rentals in Osteen

Fantasy Island Resort, Daytona Beach Shores

3.5 star property
8.4 out of 10, Very good, (71)
"We were able to check in early. Rooms were clean. They had everything that we needed in our room, such as paper towels, utensils, etc. Friendly staff. Reasonable priced. "
The price is AU$212
includes taxes & fees
28 Nov - 29 Nov
Fantasy Island Resort, Daytona Beach Shores

Tropical Suites at Sunglow Resort

4.5 star property
8.6 out of 10, Excellent, (26)
"The front desk were very polite and helpful the pool and deck were immaculate and the room was very clean and had all we needed for a stress free stay"
The price is AU$452
includes taxes & fees
4 Dec - 5 Dec
Tropical Suites at Sunglow Resort

Pirates Cove Resort Studios

3.0 star property
6.4 out of 10, (119)
"The room was great we booked very last minute. Wasn’t sure to expect. There wasn’t a door or curtain on the closet when you walk in. But otherwise it was really cute and clean. We stopped at the grocery store before we arrived they had accommodations in the room to make food that was nice. There was no interaction with any staff if you need anything. Just a text confirmation. There is a sign book but didn’t even see it till we left. Still super cute the beach was clean. Bummer the pool was...
The price is AU$221
includes taxes & fees
25 Nov - 26 Nov
Pirates Cove Resort Studios

Vacation Villas

3.0 star property
8.8 out of 10, Excellent, (284)
"Great , very comfortable spacious place to spend with your family. "
Vacation Villas

Castaways Resort Studios

3.0 star property
5.8 out of 10, (68)
"Everyone in the area is very friendly "
The price is AU$227
includes taxes & fees
24 Nov - 25 Nov
Castaways Resort Studios

Shoreline Suites & Cabana Cottages

2.0 star property
8.8 out of 10, Excellent, (362)
"Our stay was great one. The room was very clean and comfortable. "
The price is AU$178
includes taxes & fees
24 Nov - 25 Nov
Shoreline Suites & Cabana Cottages

Ocean Front Condo w/ Amazing Views, Pool & Hot Tub

9.2 out of 10, Wonderful, (51)
"We stayed for 8 nights. The Condo was nice and clean plenty of towels for our stay. Kitchen was well equipped. Would defiantly stay here again. "
The price is AU$692
includes taxes & fees
4 Dec - 5 Dec
Ocean Front Condo w/ Amazing Views, Pool & Hot Tub

~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

8.6 out of 10, Excellent, (23)
"Very impressed with employees and studio."
The price is AU$233
includes taxes & fees
22 Dec - 23 Dec
~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

Lake Front Suite -Close to all Attractions

9.4 out of 10, Exceptional, (62)
"Enjoyed our time here. "
Lake Front Suite -Close to all Attractions

New Smyrna Rv Bunkhouse Pool Private Family RV

9.4 out of 10, Exceptional, (52)
"Great place to stay. We will definitely be back. "
New Smyrna Rv Bunkhouse Pool Private Family RV

Getaway New Smyrna Beach, Sun, Pool, Shopping.

9.2 out of 10, Wonderful, (103)
"This property was rented for our workers stay in Edgewater. We canceled stay due to their discomfort in this location. Our team found another place with great conditions where they have a good rest time after daily work."
Getaway New Smyrna Beach, Sun, Pool, Shopping.

Direct Ocean Front Condo with Pool

10.0 out of 10, Exceptional, (60)
"Condo was lovely and very comfortable! Only downside was the community pool was not heated as listed."
Direct Ocean Front Condo with Pool

Beautiful View of the Atlantic Ocean from your balcony

9.6 out of 10, Exceptional, (173)
"Very comfortable room with gorgeous views and private balcony. "
Beautiful View of the Atlantic Ocean from your balcony

Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-SECURE WIFI!

8.6 out of 10, Excellent, (56)
"The building and the room we stayed in were outdated and could use some sprucing up. The bed was not comfortable, and you sunk into the middle. Very little decor in the room. One piece of "decor" was a divided serving tray. The bathtub did not drain well - while taking a shower, you'd be ankle deep in water. The view was beautiful. Centrally located to a lot of restaurants and things to do. For the price, we got what we paid for - not horrible but not worth taking pictures to post of social...
Budget Friendly OceanFront 7th Floor Condo-Clean & Comfortable-Close to Pier & Dining-SECURE WIFI!

Oceanfront Tropical Hawaiian Studio

9.6 out of 10, Exceptional, (196)
"Very pleased with our short stay at this property. Everything we needed was included, communication with host was fantastic. Pool area was really nice food/drinks at Tiki bar were good overall. People were very kind and atmosphere was perfect for what we wanted on this trip. "
Oceanfront Tropical Hawaiian Studio

Cute Studio! Remodeled! Direct Ocean Front! Pirates Cove 6th Floor

9.4 out of 10, Exceptional, (52)
"This is a great place to stay. Great location, close to stores and restaurants. Easy access to everything."
Cute Studio! Remodeled! Direct Ocean Front! Pirates Cove 6th Floor

Coastal Waters 107 - A studio poolside retreat

7.8 out of 10, Good, (19)
"Location is fantastic. Pool is large with ocean views. Beach is a few steps away. The place could be a bit cleaner and more updated,though. Dehumidifier wasn't working. Dust is visible on the ceiling fan. Coffee machine is carafe only, we were hoping for pods. The host was very responsive and helpful. Self check in was a breeze. Our 4 star review is more like 4 and a half, honestly. We will gladly come again with the hope for a tiny improvement.Thanks!"
The price is AU$352
includes taxes & fees
8 Dec - 9 Dec
Coastal Waters 107 - A studio poolside retreat

New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants

9.0 out of 10, Wonderful, (92)
"Great little place, with amenities."
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants

Stylish Boutique Guest house in Historic Winter Park.

10.0 out of 10, Exceptional, (68)
"The only thing that we had a problem with was learning how to use the TV’s. House was well appointed. Comfortable outdoor spaces."
The price is AU$541
includes taxes & fees
1 Dec - 2 Dec
Stylish Boutique Guest house in Historic Winter Park.

Breathtaking Views, Heated Pool & Beach Access!

9.2 out of 10, Wonderful, (36)
"Needed a place for one night on our trip. Great Responce .. but we did not see that the pool was under maintenance or the window air conditioners in Liv room and bedroom in stead of central air- noisy. Room very well decorated and smelled cleaning products. Great view of ocean!"
The price is AU$501
includes taxes & fees
1 Dec - 2 Dec
Breathtaking Views, Heated Pool & Beach Access!
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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Other types of properties in Osteen you may be interested in

Best Western Aku Tiki Inn

2.5 star property
8.0 out of 10, Very good, (1015)
"Great "
The price is AU$138
includes taxes & fees
1 Dec - 2 Dec
Best Western Aku Tiki Inn

Hilton Orlando/Altamonte Springs

4.0 star property
8.8 out of 10, Excellent, (1010)
"Safe, close to major highways and attractions. "
The price is AU$176
includes taxes & fees
27 Nov - 28 Nov
Hilton Orlando/Altamonte Springs

The Shores Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (1409)
"Great staff, helpful and personable! Greatbroom view (upgraded)!! Got some awesome pics. My pet was welcome no problem. My only "questionable" was the restroom which had a used razor and seemed to be mising a towel...not sure if it was thoroughly cleaned last time. Everything else was in order and neat. Would definitely stay here again!"
The price is AU$277
includes taxes & fees
1 Dec - 2 Dec
The Shores Resort & Spa
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 free WiFi 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.