Photo by Noel Benadom

Holiday Rentals in Chokoloskee

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Holiday Rentals in Chokoloskee

Waterfront 2 bedroom 1 bath with boat slip

10.0 out of 10, Exceptional, (38)
"This is our 2nd time renting this house. Location is perfect. Wake up, walk outside, get in your boat, and go! Will definitely stay here again and again. "
Waterfront 2 bedroom 1 bath with boat slip

Deep Water Access with a Panoramic View of Chokoloskee Bay

10.0 out of 10, Exceptional, (48)
"Wonderful place to stay. LM and GM are great hosts. Place was immaculate and sitting out at night looking at the oyster bars is an amazing experience. Choko is one of the last real Florida experiences left and this property exemplifies it. Thanks again!"
Deep Water Access with a Panoramic View of Chokoloskee Bay

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

9.6 out of 10, Exceptional, (122)
"Third time staying at this property. Great location with easy access to the park and Gulf. Boat slip included nearby. Clean, spacious well equipped unit with modern kitchen. Hosts very attentive. Looking forward to my next visit. Thanks Walter. "
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee-incredible fishing while enjoying Florida with friends and family.

10.0 out of 10, Exceptional, (1)
"The three of us fly fished for 3 days with local guides. This house is 3 minutes from the boat ramp. Plenty of room."
Chokoloskee-incredible fishing while enjoying Florida with friends and family.

Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft

10.0 out of 10, Exceptional, (5)
"Everything was perfect!!!!"
Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

10.0 out of 10, Exceptional, (7)
"Had an enjoyable stay with all the conveniences we needed. The owners communication was outstanding and made our stay even better. Many thanks. I would recommend this home to all my friends."
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

4-bedroom house with pool steps from the dock!

9.8 out of 10, Exceptional, (30)
"This house sleeps 12. And there were exactly 12 of us plus a four month old. We had plenty of room! The house was clean and very comfortable, perfect for a family. I would definitely rent this house again. Duane was an excellent landlord. he was available via text message and email and replied immediately whenever I contacted him."
4-bedroom house with pool steps from the dock!

River Wilderness Waterfront Cabins

2.5 star property
8.6 out of 10, Excellent, (247)
"What a gem! We loved this place; perfect for the family. Right on the water and a wonderful retreat. The whole family agreed we would like to come back."
The price is €312
includes taxes & fees
28 Dec - 29 Dec
River Wilderness Waterfront Cabins

Everglades City Cabin: Dock & Heated Pool!

8.8 out of 10, Excellent, (11)
"Good place to stay for visiting Everglades"
Everglades City Cabin: Dock & Heated Pool!

Wood cabin with private dock

7.6 out of 10, Good, (9)
"We loved this place. It’s a little rustic but had everything you need, and the location is great for exploring the Everglades. I would certainly stay here again in ever back in the area. Thank you!"
The price is €232
includes taxes & fees
23 Dec - 24 Dec
Wood cabin with private dock

Naples Marina Getaway Studio now freshly REMODELED!

9.6 out of 10, Exceptional, (10)
"If you like quiet and secluded this is the perfect place for you! Since there wasn’t a welcome book- Deb answered all my questions in timely manner. The restaurant was closed and the washer and dryers were broken - all of which was not Deb’s fault. The listing also had a hot tub and hairdryer which we weren’t present. However the pool and shower were wonderful!"
The price is €280
includes taxes & fees
3 Jan - 4 Jan 2025
Naples Marina Getaway Studio now freshly REMODELED!

Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

10.0 out of 10, Exceptional, (63)
"This makes my 3rd time staying here. It’s always a great time. Love the island feel. Great restaurants near by. Quiet neighborhood. Close to the Everglades. Love Tigertail beach. Be sure to book a boat tour out to the ten thousand islands. Lots of wildlife and beautiful scenery. We will be back again next year. Thank you for sharing you home with us. "
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

Explore the Everglades!

9.8 out of 10, Exceptional, (8)
"Close driving distance to all of our adventures. "
Explore the Everglades!

Waterfront home with kayaks, washer/dryer & fast WiFi

8.2 out of 10, Very good, (10)
"Great property on the water, but renters should be warned that Stan's bar is just across the canal, and the bands are really loud... all day long. The unit is could use upgrades throughout, especially in the master bath and kitchen. The photos in the listing make the space seem a lot newer and lighter than it is. Most screens had holes in them, so fresh air - especially in the evening when the mosquitoes were thick - was not an option. Not an issue in the summer, when AC 24/7 is the norm. But...
Waterfront home with kayaks, washer/dryer & fast WiFi

Perfect Florida Cottage

9.8 out of 10, Exceptional, (45)
"Everything was as advertised, clean, comfortable and easy access to all things in the area. Good ole fashioned Florida town, where good fishing and eating are the topics for discussion. We went to see the skunk ape. We had a great time. Except for the skeeters , I would move there in a minute. But they are en masse. We knew when we came they are at the worst in June through September but we survived. Hope it’s not another 20 years before we go back to that area. You must drive Loop Road off...
Perfect Florida Cottage

Paradise on the Bay

10.0 out of 10, Exceptional, (11)
"The apartment is very nice, cozy, super clean and with everything you need to make your stay enjoyable. The sunrise is beautiful. Very quiet area. I would come back again without hesitation."
Paradise on the Bay

Tarpon Tavern at Glades Villas-One bedroom Apartment

8.8 out of 10, Excellent, (3)
"Good value for the money. Area is still recovering from the hurricane."
Tarpon Tavern at Glades Villas-One bedroom Apartment

Extreme Naples Charters- "Comfort Zone"-Social Distancing at it's Best!

9.8 out of 10, Exceptional, (19)
"We had a great stay, & we were very comfortable. Owners were available for our questions when needed, the area was quiet at night, and the club amenities were a nice bonus."
Extreme Naples Charters- "Comfort Zone"-Social Distancing at it's Best!

The Everglades House

10.0 out of 10, Exceptional, (1)
"The house accommodations were spot on for our needs. The location on the river is fantastic! We walked to the Gun and Rod Club for dinner. Excellent! We took an airboat ride with Wootens. Another hit for all. Our 7 person party ranges from 7 to 90 yrs old."
The Everglades House

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

9.6 out of 10, Exceptional, (4)
"Loved the actual condo. Exactly as described / shown. The actual resort is a bit lacking.. ton of potential. Location is great..close enough but far enough away. Thank you for allowing us to stay!"
The price is €220
includes taxes & fees
6 Jan - 7 Jan 2025
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
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.
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Other types of properties in Chokoloskee you may be interested in

Deep Water Access with a Panoramic View of Chokoloskee Bay

10.0 out of 10, Exceptional, (48)
"Wonderful place to stay. LM and GM are great hosts. Place was immaculate and sitting out at night looking at the oyster bars is an amazing experience. Choko is one of the last real Florida experiences left and this property exemplifies it. Thanks again!"
Deep Water Access with a Panoramic View of Chokoloskee Bay

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

9.6 out of 10, Exceptional, (122)
"Third time staying at this property. Great location with easy access to the park and Gulf. Boat slip included nearby. Clean, spacious well equipped unit with modern kitchen. Hosts very attentive. Looking forward to my next visit. Thanks Walter. "
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Waterfront 2 bedroom 1 bath with boat slip

10.0 out of 10, Exceptional, (38)
"This is our 2nd time renting this house. Location is perfect. Wake up, walk outside, get in your boat, and go! Will definitely stay here again and again. "
Waterfront 2 bedroom 1 bath with boat slip
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.

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?

Deep Water Access with a Panoramic View of Chokoloskee Bay: This highly rated holiday home rental in Chokoloskee is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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 Chokoloskee Bay and Museum of the Everglades.

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.