Chokoloskee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chokoloskee holiday rentals

The Ultimate Fishing Retreat- Comfortable and Convenient!

The Ultimate Fishing Retreat- Comfortable and Convenient!
Ochopee
9.8 out of 10, Exceptional, (18 reviews)
"Phenomenal place to stay. Enjoyed everyday we were there. "
United States
Devon G.
The price is NZ$880
includes taxes & fees
1 June - 2 June
The Ultimate Fishing Retreat- Comfortable and Convenient!

River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (287 reviews)
"Such a beautiful, cozy and relaxing stay! "
United States
Patrick
The price is NZ$436
includes taxes & fees
13 May - 14 May
River Wilderness Waterfront Cabins

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
Ochopee
10.0 out of 10, Exceptional, (21 reviews)
"Cool place, beautiful inside"
United States
Sarah J
The price is NZ$574
includes taxes & fees
11 May - 12 May
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

Sunrise Waterfront Cottage

Sunrise Waterfront Cottage
Marco Island
10.0 out of 10, Exceptional, (46 reviews)
"The host always responded to my emails quickly and was very accommodating during my stay, she and her husband was great."
United States
Dean L.
The price is NZ$631
includes taxes & fees
11 May - 12 May
Sunrise Waterfront Cottage

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
Naples
9.8 out of 10, Exceptional, (11 reviews)
"Perfect location. "
United States
Jennifer E.
The price is NZ$397
includes taxes & fees
14 May - 15 May
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is NZ$314
includes taxes & fees
11 May - 12 May
Exclusive 10,000 Islands Access: Naples Studio

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (24 reviews)
"Very nice room and property - and affordable! Clean and comfortable."
United States
Vickie W.
The price is NZ$408
includes taxes & fees
11 May - 12 May
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Resort-Style Studio 15 Mi to Everglades NP

Resort-Style Studio 15 Mi to Everglades NP
Naples
6.0 out of 10, (1 review)
"The room was not very clean. The price was good but you get what you pay for. I would not stay here again! "
United States
Jodie M.
The price is NZ$314
includes taxes & fees
17 May - 18 May
Resort-Style Studio 15 Mi to Everglades NP
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chokoloskee Hotel Reviews

Find out more about Chokoloskee

Everything you need to know about Chokoloskee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chokoloskee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chokoloskee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chokoloskee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chokoloskee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chokoloskee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chokoloskee holiday rentals we have selected for you start as low as NZ$397 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chokoloskee rentals

At Expedia, we put the best Chokoloskee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chokoloskee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chokoloskee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chokoloskee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chokoloskee?

Yes, there are holiday rentals close to the most popular sights in Chokoloskee, or you can select a more secluded option if you're looking for a relaxing stay. Chokoloskee is known for its waterfront and seafood restaurants.

What are some of the best holiday rentals that Chokoloskee has to offer?

The Ultimate Fishing Retreat- Comfortable and Convenient!: This highly rated holiday home rental in Chokoloskee is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Another good choice for your trip to Chokoloskee is Deep Water Access with a Panoramic View of Chokoloskee Bay.

How many holiday rentals are there in Chokoloskee?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

While exploring the area, visit family-friendly sights like Rookery Bay Reserve Lands, or get outside and enjoy nature at Everglades National Park. In the wider area, you’ll find Smallwood Store and Chokoloskee Bay.

What are holiday rentals like in Chokoloskee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chokoloskee. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.