Osteen Vacation Rentals

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Vacation Rentals in Osteen

Silver Beach Club

3.5 star property
8.6 out of 10, Excellent, (64)
"The room were very spacious and great views!"
The price is ¥20,793
¥23,392 total
includes taxes & fees
Jun 29 - Jun 30
Silver Beach Club

Fantasy Island Resort, Daytona Beach Shores

4.0 star property
8.6 out of 10, Excellent, (101)
"The people there were very generous and made the stay there very pleasant!!"
Fantasy Island Resort, Daytona Beach Shores

Castaways Resort Studios

3.0 star property
5.8 out of 10, (77)
"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 ¥12,807
¥24,428 total
includes taxes & fees
Jun 29 - Jun 30
Castaways Resort Studios

Oceanside Inn Studios by Brightwild

3.5 star property
The price is ¥8,407
¥47,959 total
includes taxes & fees
Jul 2 - Jul 3
Oceanside Inn Studios by Brightwild

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (232)
"Absolutely amazing!!!! We will definitely stay here again!"
New Smyrna Waves by Exploria Resorts

Tropical Suites at Sunglow Resort

4.5 star property
8.8 out of 10, Excellent, (47)
"Clean, easy, family friend! Will definitely be coming back often to stay! So happy i found this place! "
The price is ¥16,176
¥52,277 total
includes taxes & fees
Jul 1 - Jul 2
Tropical Suites at Sunglow Resort

Vacation Villas

3.0 star property
8.8 out of 10, Excellent, (316)
"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

Shoreline Suites & Cabana Cottages

2.0 star property
8.8 out of 10, Excellent, (373)
"Love the location and how cute the cabanas are. "
The price is ¥19,741
¥22,209 total
includes taxes & fees
Jun 29 - Jun 30
Shoreline Suites & Cabana Cottages

Pirates Cove Resort Studios

3.0 star property
6.2 out of 10, (134)
"They are doing construction on the hotel but I didn’t notice any loud noises when we stayed. "
The price is ¥14,230
¥26,028 total
includes taxes & fees
Jun 29 - Jun 30
Pirates Cove Resort Studios

The House On Crawford COTTAGE Historic House, Independent Apartment

9.4 out of 10, Exceptional, (96)
"Cute place a 5 minute easy walk to either beach or restaurants. Fully equipped with practically anything imaginable. "
The price is ¥12,937
¥26,442 total
includes taxes & fees
Jun 29 - Jun 30
The House On Crawford COTTAGE Historic House, Independent Apartment

3-Bedroom Condo in Lovely Daytona Beach Shores with Amazing Views!

9.8 out of 10, Exceptional, (7)
"very clean "
3-Bedroom Condo in Lovely Daytona Beach Shores with Amazing Views!

Direct Ocean Front Cozy Condo with Pool - Amazing View!

9.8 out of 10, Exceptional, (76)
"Love the location. Great communication with owner. Our 4th stay with Heyl's."
Direct Ocean Front Cozy Condo with Pool - Amazing View!

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

9.0 out of 10, Wonderful, (99)
"The property is as advertised. It’s clean and has all the towels and sheets available. It’s well air conditioned and well lit. We only slept and showered for a family of 5 (with teenagers) and it worked for that purpose. "
New Smyrna Beach Cozy Pool Home, Beach, Shopping & Restaurants

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

8.8 out of 10, Excellent, (32)
"Entire apt was neat, clean, well stocked. Close to (by car) good seafood restaurants. Apt is on street side of building, but pool and beach access is just across parking lot on ground floor.Wish weather had cooperated for sunning."
The price is ¥7,260
¥23,323 total
includes taxes & fees
Jul 27 - Jul 28
~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

9.6 out of 10, Exceptional, (252)
"Wife and I were very comfortable in the unit. Close to all interested locales. We enjoyed it all."
Breath Taking Oceanfront Penthouse Condo 1 Bed 1 Bath Sleeps 4

Lake Front Suite -Close to all Attractions

9.4 out of 10, Exceptional, (73)
"Close to our airport and to state parks we wanted to visit. "
Lake Front Suite -Close to all Attractions

Ocean Front at Pirates Cove

9.2 out of 10, Wonderful, (52)
"Clean, quiet enjoyable stay !"
Ocean Front at Pirates Cove

Ocean Reef # 311 Right On The Beach! Breathtaking Views All Around!

9.8 out of 10, Exceptional, (226)
"Good place to kick back and relax"
Ocean Reef # 311 Right On The Beach! Breathtaking Views All Around!

Oceanview Condo-Clean & Comfy-PRIVATE BALCONY-WIFI in Daytona Beach Shores

10.0 out of 10, Exceptional, (6)
"All was great "
The price is ¥12,778
¥30,638 total
includes taxes & fees
Jul 6 - Jul 7
Oceanview Condo-Clean & Comfy-PRIVATE BALCONY-WIFI in Daytona Beach Shores

Dreamy oceanfront suite with kitchenette, beach access & fast WiFi

8.2 out of 10, Very Good, (44)
"Easy to book, easy to check-in, no problems whatsoever. Cute, clean place right on the beach. Worked perfect for our trip. Would definitely recommend and stay here again!"
Dreamy oceanfront suite with kitchenette, beach access & fast WiFi
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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Frequently asked questions

Can I find vacation rentals in Osteen?

Yes, we have vacation rentals in Osteen close to Pell's Citrus & Nursery, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Osteen has to offer?

Pirates Cove Resort Studios: Visitors like this Osteen vacation home rental. It 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.

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 vacation rental in Osteen like?

Vacation rentals are private properties you can stay in for several days or longer in Osteen. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.