A calm lake with a clear sky and scattered clouds, surrounded by dense green forest.

Chokoloskee Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chokoloskee holiday rentals

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

1. Amazing little fishing cabin on the water with a boat ramp in Everglades City

Amazing little fishing cabin on the water with a boat ramp in Everglades City
Everglades City
10.0 out of 10, Exceptional, (3 reviews)
"We had a fabulous stay."
United States
Christie
The price is HK$1,144
HK$2,392 total
includes taxes & fees
24 Sept - 25 Sept
Amazing little fishing cabin on the water with a boat ramp in Everglades City
A wooden deck with outdoor seating and a grill, surrounded by trees and a body of water.

2. 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 HK$1,553
HK$2,703 total
includes taxes & fees
24 Sept - 25 Sept
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
A wooden deck with a glass door leading to a balcony overlooking a body of water.

3. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (298 reviews)
"Great stay!"
United States
Quentin
The price is HK$1,790
HK$2,040 total
includes taxes & fees
24 Sept - 25 Sept
River Wilderness Waterfront Cabins
A modern living room with a sofa, armchair, and ottoman, a kitchen area with bar stools, and a ceiling fan.

4. If you prefer wildlife over nightlife this is the place for you, Fakahatchee!

If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
Copeland
10.0 out of 10, Exceptional, (5 reviews)
"Great place, the home and the fishing was phenomenal."
United States
Luke W.
The price is HK$1,569
HK$3,159 total
includes taxes & fees
27 Sept - 28 Sept
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
A kitchen with a stainless steel sink, a coffee maker, and a dishwasher.

5. Resort-style Naples Studio w/ Marina Access!

Resort-style Naples Studio w/ Marina Access!
3.0 star property
Naples
The price is HK$596
HK$1,194 total
includes taxes & fees
30 Sept - 1 Oct
Resort-style Naples Studio w/ Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

6. Naples Resort Retreat w/ Pool Access!

Naples Resort Retreat w/ Pool Access!
Naples
6.6 out of 10, (4 reviews)
"Great potential needs work no bar restaurants as advertised "
United States
Mike S.
The price is HK$455
HK$1,315 total
includes taxes & fees
29 Sept - 30 Sept
Naples Resort Retreat w/ Pool Access!
A spacious living area with wicker furniture, a fireplace, and a staircase.

7. Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (25 reviews)
"The host is amazing and very helpful. I messaged a lot and she always replied and was very nice. Will definitely book again"
United States
glynn l.
The price is HK$745
HK$1,910 total
includes taxes & fees
29 Sept - 30 Sept
Naples Marina Getaway Studio DIRECT WATER VIEWS!
A spacious living area with wicker furniture, a fireplace, and a staircase.

8. 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)
"The host did a great jobThe resort was as advertised"
United States
Skip S.
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

9. Resort-Style Naples Studio w/ Marina Access!

Resort-Style Naples Studio w/ Marina Access!
Naples
The price is HK$384
HK$1,236 total
includes taxes & fees
30 Sept - 1 Oct
Resort-Style Naples Studio w/ Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

10. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is HK$486
HK$1,350 total
includes taxes & fees
24 Sept - 25 Sept
Pool Access: Everglades Resort Retreat!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

11. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is HK$486
HK$1,350 total
includes taxes & fees
24 Sept - 25 Sept
Exclusive 10,000 Islands Access: Naples Studio
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

12. Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is HK$486
HK$1,350 total
includes taxes & fees
24 Sept - 25 Sept
Everglades Getaway 15 Mi to NP: Sail + Swim!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

13. Everglades Studio w/ Resort Amenities & Porch!

Everglades Studio w/ Resort Amenities & Porch!
Naples
6.6 out of 10, (4 reviews)
"Nice place to spend for a short stay. Unit not really set up for a long stay."
United States
James L.
The price is HK$612
HK$1,497 total
includes taxes & fees
29 Sept - 30 Sept
Everglades Studio w/ Resort Amenities & Porch!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

14. Everglades Escape w/ Outdoor Pool & Marina Access!

Everglades Escape w/ Outdoor Pool & Marina Access!
Naples
8.0 out of 10, Very good, (3 reviews)
"Great Stay!!!"
United States
Ryan S.
The price is HK$486
HK$1,350 total
includes taxes & fees
24 Sept - 25 Sept
Everglades Escape w/ Outdoor Pool & Marina Access!

15. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
The price is HK$714
HK$1,325 total
includes taxes & fees
24 Sept - 25 Sept
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

16. Dock, Pool & Tennis Courts: Naples Resort Retreat!

Dock, Pool & Tennis Courts: Naples Resort Retreat!
Naples
6.0 out of 10, (2 reviews)
"Super cute and updated. Pool was great. Short walk to beach. "
United States
Christy R.
The price is HK$612
HK$1,497 total
includes taxes & fees
29 Sept - 30 Sept
Dock, Pool & Tennis Courts: Naples Resort Retreat!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

17. Bring Your Boat: Condo w/ Pool in Naples!

Bring Your Boat: Condo w/ Pool in Naples!
Naples
4.0 out of 10, (1 review)
"no restaurant open during the week "
United States
Robert S.
The price is HK$447
HK$1,306 total
includes taxes & fees
24 Sept - 25 Sept
Bring Your Boat: Condo w/ Pool in Naples!
A spacious interior with a high ceiling, multiple levels, and a central staircase.

18. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
Naples
4.8 out of 10, (3 reviews)
"Room shown was still in use when we arrived then substituted for a non upgraded, dirty room. Heavy chemical cleaner smell, floors, kitchen, and bathroom not clean or anywhere near what was shown in listing pictures. Felt like a bait and switch. Emailed Evolve Travel upon checkout, a formal claim initiated by them. 5 days later still no resolution. "
United States
Liane H.
The price is HK$486
HK$1,350 total
includes taxes & fees
29 Sept - 30 Sept
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

19. Near the Everglades: Studio at Port of the Islands

Near the Everglades: Studio at Port of the Islands
Naples
6.0 out of 10, (2 reviews)
"Very quiet, adjacent to marina with a nice pool. Staff was very friendly and responsive."
United States
Sally G.
The price is HK$518
HK$1,384 total
includes taxes & fees
29 Sept - 30 Sept
Near the Everglades: Studio at Port of the Islands
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

20. Resort-Style Studio 15 Mi to Everglades NP

Resort-Style Studio 15 Mi to Everglades NP
Naples
7.0 out of 10, Good, (2 reviews)
"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 HK$431
HK$1,289 total
includes taxes & fees
29 Sept - 30 Sept
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.
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Top Chokoloskee Hotel Reviews

Everglades Adventures Hotel Suites by Ivey House

Everglades Adventures Hotel Suites by Ivey House

10/10 Excellent
"The room was clean and smelled fresh, the bed comfortable and the TV worked."
Matthew 1-night trip
Posted 3 days ago
Everglades Adventures Hotel Suites by Ivey House

Find out more about Chokoloskee

Search for holiday rentals in Chokoloskee on Expedia! You can easily find your home rentals, villas, holiday apartments in Chokoloskee using one of the methods below:

  • View our selection of featured holiday rentals in Chokoloskee
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  • Enter your travel dates to view the best deals on holiday rentals in Chokoloskee while they last

Look no further and take a look at our great range of rental properties in Chokoloskee!

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 Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool: This highly rated holiday home rental in Chokoloskee offers an outdoor pool, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Chokoloskee?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

Big Cypress National Preserve and Everglades National Park are a couple of lovely local spots to get outside and enjoy nature. Chokoloskee Bay and Smallwood Store are other places to visit while you're in town.

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.