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Chokoloskee Island Holiday Rentals

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Holiday Rentals in Chokoloskee Island

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee
10.0 out of 10, Exceptional, (5)
"A great property with a million dollar location, great headquarters for my 3 day stay.."
United States
Randy L.
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee
10.0 out of 10, Exceptional, (57)
"This home is an ideal destination for a fishing trip. My two brothers and I had a great time."
United States
Spencer H.
Deep Water Access with a Panoramic View of Chokoloskee Bay

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

Chokoloskee
9.6 out of 10, Exceptional, (132)
"Stayed for 11 days to do some fishing and get away from the northern US cold weather. Nice place for relaxing."
United States
Kimberly B.
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

The Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
Ochopee
9.8 out of 10, Exceptional, (13)
"Great place"
United States
Matt
The price is NZ$825
includes taxes & fees
10 Nov - 11 Nov
The Ultimate Fishing Retreat- Comfortable and Convenient!

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee
10.0 out of 10, Exceptional, (47)
"We enjoyed our stay."
United States
Peter B.
Waterfront 2 bedroom 1 bath with boat slip

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

Chokoloskee
10.0 out of 10, Exceptional, (10)
"This place had everything you need or would want if your planning a fishing trip! Close to the boat ramp as well. House was clean and just as pictured."
United States
Justin P.
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

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

Ochopee
10.0 out of 10, Exceptional, (3)
"The property was a great fit for our fishing trip! We were 4 guys and having the four bedrooms worked great. The additional refrigerators also made storing food and drink very easy. We were 3-4 minutes from marina which was perfect."
United States
Dean B.
Chokoloskee-incredible fishing while enjoying Florida with friends and family.

River Wilderness Waterfront Cabins

2.5 star property
Everglades City
8.6 out of 10, Excellent, (269)
"I would recommend this place for pure rest and relaxation "
United States
Shodo
The price is NZ$463
includes taxes & fees
10 Nov - 11 Nov
River Wilderness Waterfront Cabins

@cypresscottage

Ochopee
10.0 out of 10, Exceptional, (47)
"We would stay here again."
United States
Whitney M.
@cypresscottage

Cottage retreat with walking distance to the Dock 🐠

Everglades City
9.4 out of 10, Exceptional, (51)
"Good location to visit surrounding areas."
United States
Shelley C.
Cottage retreat with walking distance to the Dock 🐠

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples
9.6 out of 10, Exceptional, (14)
"Port of the islands is one of my favorite spots; very laid back and relaxing. Deborah's place was very cute, clean, and comfortable. Perfect for a weekend getaway!"
United States
Julie D.
The price is NZ$429
includes taxes & fees
10 Nov - 11 Nov
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat

3.0 star property
Everglades City
9.0 out of 10, Wonderful, (6)
"This little cottage was nice and in a good location. Stayed with a group of five and had plenty of room. Owner's were very nice and responsive to any questions that I had. Would recommend this place for anyone who is looking for a nice comfortable place to stay in Everglades city."
United States
Judy A.
Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat

Charming 2-bedroom cottage in superb Marco Island with AC

Marco Island
Charming 2-bedroom cottage in superb Marco Island with AC

4-bedroom house with pool steps from the dock!

Everglades City
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay very much. Perfect location and clean!"
United States
Robert L.
4-bedroom house with pool steps from the dock!

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

Ochopee
9.6 out of 10, Exceptional, (7)
"We enjoyed our visit "
United States
Armando T.
The price is NZ$624
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

Historic Home in the Heart of Everglades City

Everglades City
Historic Home in the Heart of Everglades City

Sunrise Waterfront Cottage

Marco Island
10.0 out of 10, Exceptional, (44)
"Exception host. Very nice to have all the little extras on hand waiting for you. Great location for exploring the Everglades & Marco Island beaches."
United States
Myra S.
The price is NZ$704
includes taxes & fees
10 Nov - 11 Nov
Sunrise Waterfront Cottage

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

Naples
9.8 out of 10, Exceptional, (8)
"It was a friendly neighborhood!"
United States
Mary K.
The price is NZ$441
includes taxes & fees
17 Nov - 18 Nov
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D

Naples
7.8 out of 10, Good, (13)
"Dock, pool and had everything we needed. Local manager Mandy was excellent for any questions."
United States
charles z.
Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D

Waterfront retreat with bay views, dog-friendly, & snowbird-ready

Goodland
10.0 out of 10, Exceptional, (4)
"This was our first time staying on Goodland. This home was super clean, well managed and had everything we could need. Beds were super comfortable. The tiny screened in porch was nice to be outside without bugs! We rented kayaks and took them out each morning to go check out the surrounding islands. Would definitely stay here again."
United States
Susie A.
Waterfront retreat with bay views, dog-friendly, & snowbird-ready
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 Island Hotel Reviews

Find out more about Chokoloskee Island

Everything you need to know about Chokoloskee Island 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 Island 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 Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chokoloskee Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chokoloskee Island. 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 Island 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 Island holiday rentals we have selected for you start as low as NZ$429 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chokoloskee Island rentals

At Expedia, we put the best Chokoloskee Island 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 Island 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 Island 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 Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.