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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 14 Guest Houses in Osteen with updated reviews, rates, and availability.

Sea Dip Resort Studios
Indoor pool, 2 outdoor pools

Sea Dip Resort Studios

3.0 star property
5.8 out of 10, (36)
"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 286
AED 576 total
includes taxes & fees
24 Mar - 25 Mar
Sea Dip Resort Studios
Cabin On The Lake
Front of property

Cabin On The Lake

3.0 star property
9.8 out of 10, Exceptional, (91)
"Hugo was a wonderful host. He suggested various places to visit. He made great pancakes. It was fun watching him feed the ducks. Our room was clean and had everything we needed. The house was quiet and peaceful. It's worth a return trip. "
The price is AED 529
AED 595 total
includes taxes & fees
1 Apr - 2 Apr
Cabin On The Lake
The Ann Stevens House
Exterior

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (151)
"What a beautiful, serene, magical place this is! The owners are so friendly and helpful and full of so much knowledge about the area. We loved our stay and wanted to stay longer!! "
The price is AED 511
AED 574 total
includes taxes & fees
4 Apr - 5 Apr
The Ann Stevens House
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (63)
"Perfect house, perfect location, and the host is very pleasant and easy to get in contact with. A great stay."
SPRING LAKE GETAWAY SUITE (Detached Guest 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
Peaceful Beachside Retreat
On the beach, sun loungers, beach towels

Peaceful Beachside Retreat

10.0 out of 10, Exceptional, (39)
"Mike and Candi were gracious and very attentive to all our needs. We walked and biked to beach, parks, restaurants and pickleball courts and shopping areas. Hot tub and balcony were great. Kitchenette is very small, but we grilled a lot. Main bedroom is separated by a curtain, and second bedroom has sliding glass door."
Peaceful Beachside Retreat
Dog Friendly Loft STEPS from Beach with Gas Barbecue Grill and Upstairs Deck!
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (12)
"Cozy and private. A great location and a very nice experience "
Dog Friendly Loft STEPS from Beach with Gas Barbecue Grill and Upstairs Deck!
Captain’s Quarters Along the Sea Private waterfront Suite
Miscellaneous

Captain’s Quarters Along the Sea Private waterfront Suite

10.0 out of 10, Exceptional, (75)
"This property was fantastic, clean, just overall happy with our stay. Exactly what the pictures show. The hosts were very helpful. Highly reccomend."
The price is AED 422
AED 755 total
includes taxes & fees
6 Apr - 7 Apr
Captain’s Quarters Along the Sea Private waterfront Suite
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Fridge, microwave, oven, stovetop

 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 
Adorable 1bed 1 bath guest house
Smart TV

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (23)
"Great stay while we were attending a college graduation.Plenty of room and super clean.Host was great and had all we needed. "
Adorable 1bed 1 bath guest house
City Guesthouse in beautiful Historic Downtown Sanford
TV

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
A heated 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.
Interior

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
View from property

New Smyrna Waves by Exploria Resorts

3.0 star property
9.2 out of 10, Wonderful, (204)
"I will go back for sure. Great place for a beach trip with the kids"
New Smyrna Waves by Exploria Resorts
Tropical Suites at Sunglow Resort
Outdoor pool, sun loungers

Tropical Suites at Sunglow Resort

4.5 star property
8.8 out of 10, Excellent, (37)
"I didn't realize I booked on the 10th floor. The view was amazing! We were also honored with a full red moon which was stunnind lighting the ocean surface. Crabby Joes was excellent food just a next door. Our hosts were great and the lobby people too. Love, love, love this place!"
The price is AED 410
AED 1,325 total
includes taxes & fees
15 Apr - 16 Apr
Tropical Suites at Sunglow Resort
Castaways Resort Studios
Pool

Castaways Resort Studios

3.0 star property
5.8 out of 10, (69)
"Everyone in the area is very friendly "
The price is AED 258
AED 544 total
includes taxes & fees
24 Mar - 25 Mar
Castaways Resort Studios
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.