Osteen Vacation Rentals & Ski-in/Ski-out Homes
House
9.8Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $243/Night
7 Nights - US $1,701
Hotel
9.4Exceptional
(390 Reviews)
1 Bath
- Balcony/Terrace
- Kitchen
Parking
Air Conditioner
US $109/Night
7 Nights - US $763
House
- Florida
- ·
- Volusia County
- 23.93 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $330/Night
7 Nights - US $2,309
House
- DeLand
- ·
- Deltona Lakes
- 1.78 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1001.04 ft²
View- Pet Friendly
- Parking
- Air Conditioner
US $152/Night
7 Nights - US $1,064
House
- DeLand
- ·
- Deltona Lakes
- 1.55 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
1587 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $161/Night
7 Nights - US $1,125
Cottage
- Orlando
- ·
- Lemon Bluff
- 0.23 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $181/Night
7 Nights - US $1,270
House
- DeLand
- ·
- Deltona Lakes
- 2.02 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $142/Night
7 Nights - US $992
House
- DeLand
- ·
- Deltona Lakes
- 1.82 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
8 Guests
Private Pool- Fireplace/Heating
- Pool
- Kitchen
US $192/Night
7 Nights - US $1,342
Luxury Places to Stay in Osteen
Over 321+ Luxury Places to Stay in or Near Osteen
Villa
9.2Exceptional
(17 Reviews)
6 Bedrooms
6 Baths
12 Guests
3600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $723/Night
7 Nights - US $5,063
House
4 Bedrooms
2 Baths
8 Guests
1862.16 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $720/Night
7 Nights - US $5,040
Bed & Breakfast
- DeLand
- ·
- Deltona Lakes
- 3.62 mi to center
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $648/Night
7 Nights - US $4,535
House
- DeLand
- ·
- Deltona Lakes
- 3.40 mi to center
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $630/Night
7 Nights - US $4,407
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
2800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $622/Night
7 Nights - US $4,351
House
- Orlando
- ·
- Lemon Bluff
- 0.13 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $563/Night
7 Nights - US $3,938
House
3 Bedrooms
2 Baths
7 Guests
5446.54 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $556/Night
7 Nights - US $3,892
House
9.6Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
26 Guests
2100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $536/Night
7 Nights - US $3,753
House
3 Bedrooms
2 Baths
6 Guests
1571.53 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $508/Night
7 Nights - US $3,556
Top-Rated Vacation Rentals with a Pool in Osteen
Over 55+ Top-Rated Vacation Rentals with a Pool in or Near Osteen
House
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
1665 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $320/Night
7 Nights - US $2,239
House
- DeLand
- ·
- Deltona Lakes
- 1.76 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1740 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $318/Night
7 Nights - US $2,223
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
1400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $295/Night
7 Nights - US $2,063
House
- DeLand
- ·
- Deltona Lakes
- 0.86 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1756 ft²
- Fireplace/Heating
- Pool
- Ocean View
- View
US $253/Night
7 Nights - US $1,768
House
- DeLand
- ·
- Deltona Lakes
- 1.74 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
10 Guests
1765.28 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $330/Night
7 Nights - US $2,311
House
- DeLand
- ·
- Deltona Lakes
- 1.35 mi to center
9.8Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $358/Night
7 Nights - US $2,508
Apartment
- DeLand
- ·
- Deltona Lakes
- 3.07 mi to center
9.6Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1110 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $343/Night
7 Nights - US $2,403
House
- DeLand
- ·
- Deltona Lakes
- 2.44 mi to center
9.5Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
3 Guests
1399.31 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $177/Night
7 Nights - US $1,242
Hotel
9.4Exceptional
(54 Reviews)
1 Bath
- Pool
Breakfast- Air Conditioner
- Child Friendly
US $135/Night
7 Nights - US $946
Pet-Friendly Vacation Rentals in Osteen
Over 120+ Pet-Friendly Vacation Rentals in or Near Osteen
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
1399.31 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $249/Night
7 Nights - US $1,746
House
- DeLand
- ·
- Deltona Lakes
- 2.13 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $142/Night
7 Nights - US $997
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
904.17 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $233/Night
7 Nights - US $1,629
House
- DeLand
- ·
- Deltona Lakes
- 2.01 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,238
House
- DeLand
- ·
- Deltona Lakes
- 3.35 mi to center
9.6Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $1,000
House
- DeLand
- ·
- Deltona Lakes
- 1.84 mi to center
9.4Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $140/Night
7 Nights - US $983
House
- DeLand
- ·
- Deltona Lakes
- 0.35 mi to center
9.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $254/Night
7 Nights - US $1,780
House
- DeLand
- ·
- Deltona Lakes
- 1.84 mi to center
8.4Excellent
(14 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $146/Night
7 Nights - US $1,022
House
- DeLand
- ·
- Deltona Lakes
- 3.33 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $261/Night
7 Nights - US $1,828
Large Vacation Homes & Villas in Osteen
Over 38+ Large Vacation Homes & Villas in or Near Osteen
House
- DeLand
- ·
- Deltona Lakes
- 2.89 mi to center
9.5Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $204/Night
7 Nights - US $1,428
House
- DeLand
- ·
- Deltona Lakes
- 2.57 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $377/Night
7 Nights - US $2,636
New
House
- DeLand
- ·
- Deltona Lakes
- 1.74 mi to center
1 Bedroom
1 Bath
10 Guests
2583.34 ft²
- Pool
- Parking
- Air Conditioner
- Internet
US $384/Night
7 Nights - US $2,686
House
- DeLand
- ·
- Deltona Lakes
- 1.74 mi to center
8.8Fabulous
(13 Reviews)
5 Bedrooms
4 Baths
10 Guests
1760 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $452/Night
7 Nights - US $3,165
House
- DeLand
- ·
- Deltona Lakes
- 1.66 mi to center
3 Bedrooms
2 Baths
10 Guests
1119 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $191/Night
7 Nights - US $1,336
House
9.8Exceptional
(27 Reviews)
4 Bedrooms
3 Baths
10 Guests
1960 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $360/Night
7 Nights - US $2,520
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $278/Night
7 Nights - US $1,946
House
- DeLand
- ·
- Deltona Lakes
- 2.43 mi to center
4 Bedrooms
3 Baths
14 Guests
2142 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $359/Night
7 Nights - US $2,513
House
- DeLand
- ·
- Deltona Lakes
- 2.69 mi to center
5 Bedrooms
4 Baths
11 Guests
- Pet Friendly
- Air Conditioner
- Child Friendly
Laundry
US $350/Night
7 Nights - US $2,450
Wheelchair Accessible Vacation Homes in Osteen
Over 4+ Wheelchair Accessible Vacation Homes in or Near Osteen
House
9.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
2303.48 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $319/Night
7 Nights - US $2,235
Apartment
- DeLand
- ·
- Deltona Lakes
- 1.77 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $113/Night
7 Nights - US $789
Hotel
9.6Exceptional
(70 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $155/Night
7 Nights - US $1,088
House
5.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Kitchen
- Air Conditioner
- Child Friendly
Wheelchair Accessible
US $130/Night
7 Nights - US $910
Osteen Resorts and Airbnb Homes Under $200
Over 145+ Osteen Resorts and Airbnb Homes Under $200
Apartment
9.9Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $121/Night
7 Nights - US $847
Apartment
- DeLand
- ·
- Deltona Lakes
- 2.06 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
96 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $52/Night
7 Nights - US $362
Apartment
- DeLand
- ·
- Deltona Lakes
- 2.06 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $79/Night
7 Nights - US $550
Apartment
9.8Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
699.65 ft²
- View
- Parking
- Air Conditioner
- Internet
US $184/Night
7 Nights - US $1,291
Apartment
- DeLand
- ·
- Deltona Lakes
- 0.76 mi to center
2 Bedrooms
1 Bath
7 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $119/Night
7 Nights - US $835
New
Apartment
- DeLand
- ·
- Deltona Lakes
- 4.26 mi to center
1 Bedroom
1 Bath
2 Guests
825 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $80/Night
7 Nights - US $559
House
- DeLand
- ·
- Deltona Lakes
- 2.36 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
1470 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $182/Night
7 Nights - US $1,276
House
- DeLand
- ·
- Deltona Lakes
- 0.88 mi to center
9.8Exceptional
(69 Reviews)
3 Bedrooms
2 Baths
8 Guests
1345 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $193/Night
7 Nights - US $1,354
House
- DeLand
- ·
- Deltona Lakes
- 0.92 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
7 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $196/Night
7 Nights - US $1,374
Instantly Bookable Vacation Homes in Osteen
Over 156+ Instantly Bookable Vacation Homes in or Near Osteen
House
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1582 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $264/Night
7 Nights - US $1,847
House
- DeLand
- ·
- Deltona Lakes
- 2.62 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $242/Night
7 Nights - US $1,693
House
- DeLand
- ·
- Deltona Lakes
- 2.27 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $233/Night
7 Nights - US $1,630
House
- DeLand
- ·
- Deltona Lakes
- 1.94 mi to center
9.4Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
9 Guests
1356 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $279/Night
7 Nights - US $1,950
House
- DeLand
- ·
- Deltona Lakes
- 1.55 mi to center
9.2Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1864 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $200/Night
7 Nights - US $1,400
House
- DeLand
- ·
- Deltona Lakes
- 2.31 mi to center
9.0Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1976 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $381/Night
7 Nights - US $2,668
House
- DeLand
- ·
- Deltona Lakes
- 2.74 mi to center
9.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
9 Guests
1385 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $269/Night
7 Nights - US $1,885
House
- DeLand
- ·
- Deltona Lakes
- 2.09 mi to center
6.0Good
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $163/Night
7 Nights - US $1,144
House
- DeLand
- ·
- Deltona Lakes
- 1.12 mi to center
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $139/Night
7 Nights - US $971
Book a Last Minute Place to Stay in Osteen
About Osteen Vacation Rentals
Explore over 330 vacation rentals in Osteen with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Osteen for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Osteen. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Osteen tailored to your preferences. On average, these rentals offer 803.77 ft² of space, and are priced at an average of US $246 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Osteen at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Osteen
| Type | Count |
|---|---|
| Vacation Homes | 235 |
| Holiday Apartments | 62 |
| Cottages | 10 |
| Cabin Rentals | 5 |
| Villas | 4 |
| Unique Vacation Rentals | 3 |
| B&B | 2 |
| Others | 2 |
Use these Quick Filters to Find a Vacation Rental in Osteen
★ Pro Tip: Discover Your Ideal Vacation Rental in Osteen with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Osteen, FL
View the weather forecast for Osteen before booking your Osteen Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Osteen, FL
Sunski offers a large selection of top attractions around Osteen . Research things to do on your vacation before you visit Osteen.
Other Places to Stay in Osteen, FL
Frequently Asked Questions About Osteen?
What are the top vacation rentals in Osteen?
When organizing your trip to Osteen, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Osteen. Peruse our collection of highly-rated properties and secure your reservation today.
- Historic Cottage, super clean, comfortable and well equipped.
- Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
- Charming bungalow in Sanford's historical district
- Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
- Day Trip to Disney: Deltona Escape w/Patio
- Serenity @ Court
- Historic Hotspot Walk to Downtown Fun Luxury Beds
- The Cozy Euphoric cottage nestled in nature with relaxing River front views.
- Lovely RV with outdoor pool and Jacuzzi.
- Quiet Lakeside home BBQ, RELAX, FISH AND REPEAT
How many vacation rentals have private pools in Osteen?
Uncover 17 vacation rentals boasting private pools near Osteen. Explore top-rated RBO homes offering access to a swimming pool:
- Little Lux House, Swim Spa & Patio Oasis -on 2 acres
- Cozy 4bed 2bth villa - daytona beach
- ⭐️ Pool ⭐️ Game Room ⭐️ BBQ ⭐️ Fire Pit ⭐️ Coffee Bar
- Alameda Homestay.n
Which vacation homes or resorts in Osteen are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Osteen. Enjoy great views, locations and save money with SunSki Resorts.™
- Condo w/Pool & Beach Access Near Theme Park
- Charming Retreat - Your Perfect Getaway!
- Deltona Lake House, Day Trip to Disney & Universal
How many SunSkiResorts vacation rentals or resorts are available in Osteen?
Discover the ideal vacation rental in Osteen with SunSki Resorts™. We provide an extensive selection of over 330 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Osteen.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Deltona Lakes Vacation Rentals in Orlando, Florida | 76 |
People Also Ask
Finding the best prices in Osteen
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