Pine Key holiday lettings

We found 161 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Pine Key that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Can I find holiday rentals in Pine Key?
Yes, there are holiday rentals close to the most popular sights in Pine Key, or you can select a more secluded option if you're looking for a relaxing stay.
What can I see and do in Pine Key?
While exploring the area, visit family-friendly sights like Splash Island Water Park, or get outside and enjoy nature at Tampa Bay. John's Pass Village & Boardwalk and Eckerd College are a couple of places you'll find in the wider area.
What are holiday rentals like in Pine Key?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Key. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip.