Deals on vacations and trips to Osteen
Save when you book Osteen package deals
Osteen flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $814, price is now $350 per person
$350
per person
Aug 4 - Aug 11
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Palazzo Lakeside Hotel
Price was $1,299, price is now $354 per person
$354
per person
Aug 18 - Aug 25
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Westgate Town Center Resort
Save 100% on your flight
Price was $821, price is now $359 per person
$359
per person
Aug 4 - Aug 11
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Save 100% on your flight
Price was $1,101, price is now $514 per person
$514
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,640, price is now $864 per person
$864
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
Top Osteen hotels deals
Sheraton Orlando North Hotel
600 N Lake Destiny Dr Maitland FL
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $95 total per night
$95 total
Jul 1 - Jul 2
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and concierge services.
Pool
Hot Tub
Perry's Ocean Edge Resort
2209 S Atlantic Ave Daytona Beach Shores FL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $128 total per night
$128 total
Jun 9 - Jun 10
Total with taxes and fees
2 outdoor pools, an indoor pool, and a hot tub are all featured at this smoke-free resort. Families will appreciate the children's pool and barbecue grills. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Hot Tub
Hilton Orlando/Altamonte Springs
350 S Northlake Blvd Altamonte Springs FL
$126 nightly
The price is $143 total per night
$143 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Nautilus Inn
1515 S Atlantic Ave Daytona Beach FL
$104 nightly
The price is $117 total per night
$117 total
Jun 11 - Jun 12
Total with taxes and fees
This hotel features an outdoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a garden are also offered.
Pool
Hot Tub
The Shores Resort & Spa
2637 S Atlantic Avenue Daytona Beach Shores FL
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $166 total per night
$166 total
Jun 16 - Jun 17
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Pool
Hot Tub
Bahama House
2001 S Atlantic Ave Daytona Beach Shores FL
$145 nightly
The price is $163 total per night
$163 total
Jun 3 - Jun 4
Total with taxes and fees
This hotel features an outdoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Hot Tub
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.
Popular places to visit
Wiregrass Prairie Preserve
Explore the great outdoors at Wiregrass Prairie Preserve, a lovely green space in Osteen. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
Pell's Citrus & Nursery
Enjoy an outing to Pell's Citrus & Nursery during your stay in Osteen. While you're in the area, stroll along the lakeside.
Frequently asked questions
Photos of local treasures
Browse Osteen vacation photos for more inspiration
