Kissimmee Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Save 100% on your flight

per person

Jul 19 - Jul 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 3.5-star beach hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vilano Beach and Castillo de San Marcos National Monument are located nearby.

Meliá Orlando Celebration

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star spa hotel in Celebration. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Old Town are located nearby.

Westgate Palace Hotel / Universal / I-Drive

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.

Westgate Town Center Resort

per person

Jul 19 - Jul 26

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.

Westgate Vacation Villas Resort

per person

Jul 19 - Jul 26

found 5 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.

Westgate Towers Resort

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

per person

Jul 19 - Jul 26

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Villas At Regal Palms

Save 100% on your flight

per person

Jul 19 - Jul 26

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this 4-star spa aparthotel in Davenport. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Disney's Animal Kingdom® Theme Park and ChampionsGate Golf Club are located nearby.

Kissimmee Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Vilano Beach

Save 100% on your flight

per person

Jul 19 - Jul 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Westgate Palace Hotel / Universal / I-Drive

Florida Center

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

per person

Jun 10 - Jun 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Westgate Vacation Villas Resort

Save 100% on your flight

per person

Jun 11 - Jun 15

found 24 hours ago

Roundtrip flight included

Chicago (ORD) to Orlando (MCO)

Kissimmee Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.

Palazzo Lakeside Hotel

Save 100% on your flight

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)