Grab your popcorn and your passport! Set jetting is your ticket to stepping into your favorite TV and movie scenes. Staypineapple cities are where iconic shows and films come to life. Pack your bags — it’s time for a reel adventure!

Every baseball fan needs a stadium bucket list! From iconic classics to modern showstoppers, these must-visit ballparks deliver epic views, electric crowds and unforgettable game-day vibes.

Pets stay free with our Pineapple Pup Plus One Package

Lulu of @hansandlulu was crowned top dog in our 8th Annual Dash, The Pineapple Pup’s Costume Contest!

We took top spots for Best Pet-Friendly Getaway two years running!

Our partnership with Procure Impact helps support our community through thoughtful sourcing

Unleash your creativity and enter your dog into Dash, The Pineapple Pup’s Costume Contest!

Celebrate the special furr-iend who fills your life with happiness!

Staypineapple Chicago ranks #3 for the Best Boutique Hotel in the nation!

Staypineapple hotels have once again landed top spots on Tripadvisor!