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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 15 Guest Houses in Osteen with updated reviews, rates, and availability.

Sea Dip Resort Studios
Pool

Sea Dip Resort Studios

3.0 star property
6.0 out of 10, (32)
"I went for on a solo-trip to get away from the snow. For me, this was a perfect quiet location. The front desk staff is friendly and helpful. My room was clean and beautifully furnished. I felt like it was my own beach condo. I love that I can see the beach from the bed. The owner was helpful if I needed something. There’s a private beach and 2 pools (indoor and outdoor). I felt safe, and perfectly comfortable and happy here for a 3-night stay. Thank you."
The price is AED 323
AED 617 total
includes taxes & fees
26 Feb - 27 Feb
Sea Dip Resort Studios
Cabin On The Lake
Front of property

Cabin On The Lake

3.0 star property
10.0 out of 10, Exceptional, (85)
"Overall good. Just a little turned off by the restrictions, no food or drinks in the room which I understand but still! Nicely maintained place"
The price is AED 680
AED 764 total
includes taxes & fees
10 Feb - 11 Feb
Cabin On The Lake
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Detached Guesthouse over our 3 Car Garage

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (59)
"The host, location and hospitality were superb. 5 out of 5 stars "
SPRING LAKE GETAWAY SUITE (Detached Guest House)
The Ann Stevens House
Front of property

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (145)
"Beautiful historic property with welcoming hosts."
The price is AED 584
AED 657 total
includes taxes & fees
10 Feb - 11 Feb
The Ann Stevens House
Winter Park Getaway
Terrace/patio

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway
Dog Friendly Loft STEPS from Beach with Gas Barbecue Grill and Upstairs Deck!
Living Room Area with Dining Table

Dog Friendly Loft STEPS from Beach with Gas Barbecue Grill and Upstairs Deck!

10.0 out of 10, Exceptional, (10)
"Overall, everything was great. Fun Coast rentals was extremely responsive to any of my questions. The location was very convenient to the beach. The main road is a little loud, but not terrible. The space was perfect for what we needed. Everything was clean. The bed was comfy. We enjoyed our stay here and would recommend. "
The price is AED 1,255
AED 2,160 total
includes taxes & fees
16 Feb - 17 Feb
Dog Friendly Loft STEPS from Beach with Gas Barbecue Grill and Upstairs Deck!
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Private kitchen

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (79)
"The house was clean and pretty and perfect!! It’s all updated. Beds were super comfy and warm (it was cold the weekend we stayed). We did have an issue with a couple of minor things but Mike came over instantly and fixed them immediately. He was very attentive and very friendly and I enjoyed talking with him! We stayed for a soccer tournament and it was super close to Seminole Soccer Complex. I would absolutely stay there again! "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Captain’s Quarters Along the Sea Private waterfront Suite
On the water

Captain’s Quarters Along the Sea Private waterfront Suite

10.0 out of 10, Exceptional, (72)
"This place was perfect for us! We had everything we needed here and a wonderful host. We enjoyed our time fishing in the Mosquito Lagoon. Thank You! "
The price is AED 422
AED 766 total
includes taxes & fees
9 Mar - 10 Mar
Captain’s Quarters Along the Sea Private waterfront Suite
Peaceful Beachside Retreat
Beach sunrise just steps away!

Peaceful Beachside Retreat

10.0 out of 10, Exceptional, (38)
"The accommodations were very well appointed and comfortable. Candy and Dave were great hosts and very responsive. Definitely recommend this property!"
Peaceful Beachside Retreat
Tiny Cottage Farm House!
Dining

Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (16)
"The tiny cottage was very well prepared and so cute. It is in a perfect area very quiet and calm. I would highly recommend for a small family for a mini vacation. "
Tiny Cottage Farm House!
Adorable 1bed 1 bath guest house
King bed, dresser, luggage rack, plenty of closet space with full mirror

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (22)
"Our stay was perfect. The accommodations and hosts were excellent. Will definitely consider it again if/when coming to orlando. "
Adorable 1bed 1 bath guest house
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

9.8 out of 10, Exceptional, (8)
"The unit was nice though the AC was not operating properly. The Hosts were very understanding and immediately offer/processed refund and assisted in instructing us on method of cancelation to get full refund from VRBO. VRBO was also extremely prompt in processing a our full refund. This was a first for us using VRBO and was very skeptical but after this experience I will not have any reservation about using VRBO again as well as booking through this host. The AC issues were out of the hosts...
City Guesthouse in beautiful Historic Downtown Sanford
Private Poolside Guest House In Winter Park/Orlando
Pool

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very Good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando
Secluded and Quiet. View of the river and sunsets. Short walk to Flagler Ave.
Exterior

Secluded and Quiet. View of the river and sunsets. Short walk to Flagler Ave.

2.0 star property
Secluded and Quiet. View of the river and sunsets. Short walk to Flagler Ave.
NEW YEAR AT THE BEACH!
Beach

NEW YEAR AT THE BEACH!

NEW YEAR AT THE BEACH!
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 property types in Osteen

New Smyrna Waves by Exploria Resorts
Outdoor pool

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (184)
"The check in process was a little quirky and Expedia reservation had zero instructions or contact info for the property. Ended up just googling the property for the phone number to call for instructions. "
New Smyrna Waves by Exploria Resorts
Tropical Suites at Sunglow Resort
Pool

Tropical Suites at Sunglow Resort

4.5 star property
9.0 out of 10, Wonderful, (34)
"The rooms were clean and well appointed, and we enjoyed the balcony and the beach. The staff was friendly and helpful- we recommend this property for value and a great experience!"
The price is AED 489
AED 1,355 total
includes taxes & fees
10 Feb - 11 Feb
Tropical Suites at Sunglow Resort
Fantasy Island Resort, Daytona Beach Shores
Front of property

Fantasy Island Resort, Daytona Beach Shores

4.0 star property
8.6 out of 10, Excellent, (82)
"Friendly services, great rooms! "
The price is AED 450
AED 630 total
includes taxes & fees
24 Feb - 25 Feb
Fantasy Island Resort, Daytona Beach Shores
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.