Search Villas in Osteen

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Villas in Osteen

Vacation Villas
Exterior

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
SeaWoods VILLA. WALK to the Beach!
Exterior

SeaWoods VILLA. WALK to the Beach!

9.8 out of 10, Exceptional, (34)
"This house was gorgeous, looked newly renovated, very clean and had everything we needed! "
SeaWoods VILLA. WALK to the Beach!
SEACLUSION..Private Family & Pet Friendly Villa by the SEA! Beach/POOLS/Trails!
Property grounds

SEACLUSION..Private Family & Pet Friendly Villa by the SEA! Beach/POOLS/Trails!

10.0 out of 10, Exceptional, (96)
"Very relaxing, awesome stay"
SEACLUSION..Private Family & Pet Friendly Villa by the SEA! Beach/POOLS/Trails!
Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs
Exterior detail

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs
Sea Woods Villa - 3 pools - steps to the Beach
Property grounds

Sea Woods Villa - 3 pools - steps to the Beach

9.8 out of 10, Exceptional, (117)
"My wife and I loved this place. A very clean and quiet setting with pools and tennis courts. A short walk or drive to the beach with the Canaveral National Seashore a few miles away. The bedrooms and bathrooms were clean and comfortable with plenty of bedding and towels. The kitchen has everything you need and the washer and dryer were very convenient. I would recommend to anyone."
Sea Woods Villa - 3 pools - steps to the Beach
Sea Woods Villa 4432- 3bdrm/2Bath
A heated pool

Sea Woods Villa 4432- 3bdrm/2Bath

10.0 out of 10, Exceptional, (4)
"Beautiful villa in an enchanted forest!Decorations are gorgeous and it was immaculate.Loved the trees… "
Sea Woods Villa 4432- 3bdrm/2Bath
Modern Coastal 2 bed 2 bath villa, pet friendly, 2 miles from beach
Exterior

Modern Coastal 2 bed 2 bath villa, pet friendly, 2 miles from beach

Modern Coastal 2 bed 2 bath villa, pet friendly, 2 miles from beach
Charming Winter Park 3 Bedroom Villa with Pool
Terrace/patio

Charming Winter Park 3 Bedroom Villa with Pool

9.8 out of 10, Exceptional, (9)
"Great, quiet little spot. Had everything we needed. Great location too! "
Charming Winter Park 3 Bedroom Villa with Pool
Come Enjoy Beach Life In Spacious Elegance.
Exterior

Come Enjoy Beach Life In Spacious Elegance.

10.0 out of 10, Exceptional, (27)
"The house was so well located nd laid out conveniently, All necessary daily living items were on hand. The hosts made very special efforts to make this a great experience for our 50th Anniversary celebration!"
Come Enjoy Beach Life In Spacious Elegance.
Otium Villa - Waterfront, intercoastal villa with a Spa-like feel.
Outdoor dining

Otium Villa - Waterfront, intercoastal villa with a Spa-like feel.

9.6 out of 10, Exceptional, (10)
"Awesome property amazing sun rise"
Otium Villa - Waterfront, intercoastal villa with a Spa-like feel.
Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!
Terrace/patio

Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!

10.0 out of 10, Exceptional, (3)
"We absolutely loved our stay and it was nice and close to the Winter Park restaurants (Park Ave), Rollins College; as well as, has a nice lake/park to go walking nearby. Quiet neighborhood and the outdoor pool/spa was a nice retreat after a busy day. "
The price is SAR 2,158
SAR 4,115 total
includes taxes & fees
8 Sep - 9 Sep
Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!
Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.
Exterior

Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.

9.4 out of 10, Exceptional, (42)
"Worked well for our team. Lots of room for teenagers to lay around"
Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Exterior

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

9.0 out of 10, Wonderful, (2)
"The stay was great. There was a slight smell of a chemical odor but not overwhelming. The bed was comfy with clean sheets and there were enough clean towels. Made friends with the local cat. Overall, its was a great stay!"
The price is SAR 304
SAR 689 total
includes taxes & fees
2 Sep - 3 Sep
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Walk to Lake: Stunning Central Florida Home!
Terrace/patio

Walk to Lake: Stunning Central Florida Home!

9.8 out of 10, Exceptional, (53)
"The house was beautiful, easy to find and very clean. Had everything we needed and would definitely stay again."
Walk to Lake: Stunning Central Florida Home!
Elegant 6-bedroom, 6-bath home, sleeps 12. Ideal for large groups with Optional Banquet Room
Exterior

Elegant 6-bedroom, 6-bath home, sleeps 12. Ideal for large groups with Optional Banquet Room

9.2 out of 10, Wonderful, (14)
"Great house with plenty of space. "
Elegant 6-bedroom, 6-bath home, sleeps 12. Ideal for large groups with Optional Banquet Room
Seconds from the ocean, one bedroom villa #4
Exterior

Seconds from the ocean, one bedroom villa #4

Seconds from the ocean, one bedroom villa #4
Aruba Collection
Exterior

Aruba Collection

4.0 star property
9.6 out of 10, Exceptional, (4)
"The best place ive ever stayed at. Very friendly and accommodating. Absolutely loved my stay."
Aruba Collection
“Harmony”_
Exterior

“Harmony”_

10.0 out of 10, Exceptional, (29)
"Very clean and beautifully decorated vrbo. Had everything we needed for an enjoyable stay."
“Harmony”_
Villa with Patio & Shared Pools, Sauna, Tennis & Gym - One Block to Beach, Dogs OK
Property grounds

Villa with Patio & Shared Pools, Sauna, Tennis & Gym - One Block to Beach, Dogs OK

9.0 out of 10, Wonderful, (59)
"Location was convenient to beach and Flagner Ave! The pool was very nice. The community was very quiet, beautiful with the all the plants, trees, etc and great for walking dogs. Highly recommend and would stay again!"
Villa with Patio & Shared Pools, Sauna, Tennis & Gym - One Block to Beach, Dogs OK
Walk to Lake: Stunning Central Florida Home!
Interior

Walk to Lake: Stunning Central Florida Home!

3.0 star property
Walk to Lake: Stunning Central Florida Home!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osteen Hotel Reviews

Frequently asked questions

Why book your villa in Osteen with Expedia?
We think that vacations shouldn't be hard, so if you're searching for villas at an affordable rate, Expedia can help. Save money and choose an all-inclusive stay, or splurge on a luxe villa to spoil your sweetheart. Our search filters make it simple to find an escape in Osteen that you'll adore.
How can I find cheap villas in Osteen?
With Expedia's helpful filter tool, sourcing cheap villas in Osteen is easy. To discover stays that give you the most bang for your buck, narrow down your search by star rating, amenities and budget.