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Chokoloskee Island Holiday Rentals

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Holiday Rentals in Chokoloskee Island

Waterfront 2 bedroom 1 bath with boat slip
10.0 out of 10, Exceptional, (46)
"The house was perfect get away and very clean. It had everything you needed for your stay in Chokoloskee. If I was going back I would stay there again."
United States
Connie T.
Waterfront 2 bedroom 1 bath with boat slip
Deep Water Access with a Panoramic View of Chokoloskee Bay
10.0 out of 10, Exceptional, (55)
"Property was in great location Property owner was friendly "
United States
Michelle
Deep Water Access with a Panoramic View of Chokoloskee Bay
The Ultimate Fishing Retreat- Comfortable and Convenient!
2.0 star property
9.8 out of 10, Exceptional, (13)
"Great place"
United States
Matt
The price is AU$712
includes taxes & fees
26 Oct - 27 Oct
The Ultimate Fishing Retreat- Comfortable and Convenient!
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
10.0 out of 10, Exceptional, (4)
"Will book again"
United States
ME C.
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
9.6 out of 10, Exceptional, (132)
"Well represented "
United States
Donald S.
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise
10.0 out of 10, Exceptional, (10)
"Fantastic house, quiet ,extremely clean and well stock, we loved it and would love to come back in the near future .Thank you Maureen and Brock for this dream place Maria and Richard G"
United States
maria g.
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise
Chokoloskee-incredible fishing while enjoying Florida with friends and family.
10.0 out of 10, Exceptional, (3)
"The three of us fly fished for 3 days with local guides. This house is 3 minutes from the boat ramp. Plenty of room."
United States
Ron C.
Chokoloskee-incredible fishing while enjoying Florida with friends and family.
River Wilderness Waterfront Cabins
2.5 star property
8.6 out of 10, Excellent, (268)
"I would recommend this place for pure rest and relaxation "
United States
Shodo
The price is AU$412
includes taxes & fees
19 Oct - 20 Oct
River Wilderness Waterfront Cabins
Cottage retreat with walking distance to the Dock 🐠
9.4 out of 10, Exceptional, (48)
"Good location to visit surrounding areas."
United States
Shelley C.
Cottage retreat with walking distance to the Dock 🐠
@cypresscottage
10.0 out of 10, Exceptional, (47)
"We had a great stat and would absolutely stay here again"
United States
Jeff K.
@cypresscottage
Naples Marina Getaway Studio now freshly REMODELED!
9.6 out of 10, Exceptional, (14)
"Best stay I've had in a very long time. The place is awesome, great restaurant, nice and quiet, and close to everything. Will visit again!! "
United States
Rodney
The price is AU$380
includes taxes & fees
24 Oct - 25 Oct
Naples Marina Getaway Studio now freshly REMODELED!
Lostman's Lodge -Everglades City, Sunset View,Pool
10.0 out of 10, Exceptional, (11)
"Great accommodations and beautiful scenery "
United States
michael
Lostman's Lodge -Everglades City, Sunset View,Pool
Historic Home in the Heart of Everglades City
Historic Home in the Heart of Everglades City
Getaway in the Everglades
10.0 out of 10, Exceptional, (39)
"This was an amazing place with old Florida charm."
United States
KJ T.
Getaway in the Everglades
4-bedroom house with pool steps from the dock!
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!
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
9.8 out of 10, Exceptional, (8)
"It was a friendly neighborhood!"
United States
Mary K.
The price is AU$362
includes taxes & fees
27 Oct - 28 Oct
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
7.8 out of 10, Good, (13)
"This makes our second year staying at this exact house and we are in love with it! It is so relaxing and the pool is amazing along with the view and sunsets in the afternoon! I highly recommend this as a stay. It is always super clean and perfect for our whole stay! I hope to come back to it next year as well!"
United States
Leann B.
Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D
Waterfront retreat with bay views, dog-friendly, & snowbird-ready
10.0 out of 10, Exceptional, (4)
"We had a very good stay at this house. It was clean, had everything we needed and was in a convenient location. We would definitely recommend. "
United States
Russell M.
Waterfront retreat with bay views, dog-friendly, & snowbird-ready
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
9.6 out of 10, Exceptional, (7)
"Very private and clean with everything you need for the weekend."
United States
Joseph C.
The price is AU$536
includes taxes & fees
19 Oct - 20 Oct
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
Sunrise Waterfront Cottage
10.0 out of 10, Exceptional, (44)
"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 AU$604
includes taxes & fees
30 Oct - 31 Oct
Sunrise Waterfront Cottage
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 favourite 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 depend 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 AU$362 per night. Entering your travel dates in the search wizard might find you 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.