Search Villas in Osteen

    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

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Villas in Osteen

Vacation Villas
Full-size fridge, microwave, oven, stovetop

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
SeaWoods VILLA. WALK to the Beach!
Outdoor pool, a heated pool

SeaWoods VILLA. WALK to the Beach!

9.8 out of 10, Exceptional, (26)
"Great accommodations (clean and pleasant). Comfortable beds in both guest room and master. Across the street from the ocean in a friendly, forested community. We hope to stay here again."
SeaWoods VILLA. WALK to the Beach!
Otium Villa - Waterfront, intercoastal villa with a Spa-like feel.
Outdoor dining

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

9.4 out of 10, Exceptional, (6)
"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!
Fridge, microwave, oven, stovetop

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 2,288
SAR 4,302 total
includes taxes & fees
28 Jul - 29 Jul
Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!
Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs
Pool

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs
SEACLUSION..Private Family & Pet Friendly Villa by the SEA! Beach/POOLS/Trails!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (95)
"Very well decorated, comfortable furniture, very clean, a nicely equipped kitchen. Unit is close to beach and walking trails, great location to restauranrs. Host very good at communication"
SEACLUSION..Private Family & Pet Friendly Villa by the SEA! Beach/POOLS/Trails!
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Terrace/patio

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 334
SAR 722 total
includes taxes & fees
25 Jul - 26 Jul
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
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, (116)
"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, (2)
"This place was beautiful, exactly as described in the listing, and so generously supplied. Our family of 7 had ample room, easily went back and forth to the beach and pool, and thoroughly enjoyed our time. Highly recommend!"
Sea Woods Villa 4432- 3bdrm/2Bath
Modern Coastal 2 bed 2 bath villa, pet friendly, 2 miles from beach
Smart TV

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
Vacation Villa next to pool
Pool

Vacation Villa next to pool

2.0 out of 10, (1)
"Hard to rate this because we didn't stay. We arrived at the location with zero information on check-in, other than the address. We reached out to the owner and heard nothing, and the voicemail was full and out texts went unanswered. The property had people going in and out of the main house, but no one came out to check with us. Reached out to VRBO customer service and they got us moved to another spot for our trip. Neighborhood was nice and seemed quiet. "
The price is SAR 281
SAR 455 total
includes taxes & fees
25 Jul - 26 Jul
Vacation Villa next to 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.
2 Bdrm 2 Bath Sea Woods Villa-Unit 4406
Pool

2 Bdrm 2 Bath Sea Woods Villa-Unit 4406

9.4 out of 10, Exceptional, (6)
"We enjoyed our stay! Clean and comfortable!"
2 Bdrm 2 Bath Sea Woods Villa-Unit 4406
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, (41)
"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.
Charming Winter Park 3 Bedroom Villa with Pool
Property grounds

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

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

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

9.2 out of 10, Wonderful, (14)
"Love the house "
Elegant 6-bedroom, 6-bath home, sleeps 12. Ideal for large groups with Optional Banquet Room
Cozy Gated Nature Walk to MallParkPublix 2Story
Terrace/patio

Cozy Gated Nature Walk to MallParkPublix 2Story

9.0 out of 10, Wonderful, (2)
"Very nice and cozy. Spiral staircase might be off putting to some. Clean, nice and quiet. Would definitely stay here again."
Cozy Gated Nature Walk to MallParkPublix 2Story
Walk to Lake: Stunning Central Florida Home!
Outdoor pool

Walk to Lake: Stunning Central Florida Home!

10.0 out of 10, Exceptional, (51)
"Was great to use the property for a few days with our family. it had everything we needed. "
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

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.