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Chokoloskee Vacation Rentals

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Vacation Rentals in Chokoloskee

Deep Water Access with a Panoramic View of Chokoloskee Bay
10.0 out of 10, Exceptional, (47)
"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
Waterfront 2 bedroom 1 bath with boat slip
10.0 out of 10, Exceptional, (34)
"Awesome place, very clean and well equipped. Probably the nicest and most accommodating hosts we have experienced so far We definitely plan to be back"
Waterfront 2 bedroom 1 bath with boat slip
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
9.6 out of 10, Exceptional, (117)
"Wanted to bring the family down to experience the wilds of the Everglades and spend some time in a part of Florida that hadn’t been turned into a tourist trap. Chokoloskee and Big Blue came through spectacularly. The natural beauty and experiences here are something that will always stick with us. The host Walter was top notch in offering ideas of places to go and things to see, great in communicating with us. We had a snag with our plans on staying elsewhere the night before we were supposed...
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
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Two bedroom home fully furnished.
10.0 out of 10, Exceptional, (3)
"Not much parking with a boat trailer. The people are very nice around there,and you can get fuel and bait and tackle all at the same place and don’t have to drive up town. Overall perfect location. I will keep coming back for sure."
Two bedroom home fully furnished.
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
River Wilderness Waterfront Cabins
2.5 star property
8.4 out of 10, Very Good, (241)
"Great view on the water - watched dophins swimming by and many birds. Very nice cabin. Had all we needed for our first visit to the area. comfortable beds. Kitchen well stocked. Convenient to all local attractions. Great staff - very friendly and helpful."
The price is ¥30,974
¥35,310 total
includes taxes & fees
Jun 6 - Jun 7
River Wilderness Waterfront Cabins
4-bedroom house with pool steps from the dock!
9.8 out of 10, Exceptional, (29)
"This is our second time staying with Duane at the Everglades home. We love it here. Our family has been fishing in EGC for more than 60 years and it is always a tradition for us. This home fits our family of 7 with room to spare. Having the pool after a long day of fishing was relaxing and cooling especially for the kiddos. Be prepared to scoop crabs out of the pool! (It became a fun morning activity with the kids) Great kitchen, comfy beds, big couch, really amazing place. There is a dock area...
4-bedroom house with pool steps from the dock!
Port of The Islands Naples Marina getaway!
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 ¥18,584
¥45,353 total
includes taxes & fees
Jun 6 - Jun 7
Port of The Islands Naples Marina getaway!
Waterfront dog-friendly home with kayaks, washer/dryer & fast WiFi
8.6 out of 10, Excellent, (8)
"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 dog-friendly home with kayaks, washer/dryer & fast WiFi
Wood cabin with private dock
9.0 out of 10, Wonderful, (6)
"The cabin was as pictured But we had no check in info before we arrived just a note that we could check in early. So we had to email the owner/property manager for lock combo. Unsettling because there aren’t many options if we couldn’t get into our room in Everglades city. Fortunately he responded within 15-20 minutes Which seemed like forever. When we got in the ac was off. South Florida is hot in May… took most of the evening to cool off. Stay was uneventful, but again no instructions about...
The price is ¥17,036
¥36,534 total
includes taxes & fees
Jun 13 - Jun 14
Wood cabin with private dock
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
10.0 out of 10, Exceptional, (62)
"Great vacation! House was very clean and conveniently located to the marina. 5 stars!"
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
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!
Marina Fish- Boat and Relax in this Paradise 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 ¥15,487
¥41,451 total
includes taxes & fees
Jun 6 - Jun 7
Marina Fish- Boat and Relax in this Paradise in Naples, Florida!
Perfect Florida Cottage
9.8 out of 10, Exceptional, (43)
"We had a great stay at this Everglades. It was as advertised, clean and tastefully decorated. The host was very helpful with timely responses to our questions. We will be back."
Perfect Florida Cottage
Sunny hotel-style studio with pool, game room, sauna, tennis, restaurant, gym
Sunny hotel-style studio with pool, game room, sauna, tennis, restaurant, gym
Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ
Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ
Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D
7.0 out of 10, Good, (7)
"This house is great with a beautiful, peaceful location. It could’ve been a little cleaner (we arrived to an almost full recycling bin and a hairball in the shower), but the house was otherwise clean. The pool was great, especially at sunset. The kitchen is awesome, and the house has nice finishes. The air conditioning had an issue while we were there, but still worked somewhat. The house was in the high 80s inside when we arrived, but property management sent someone out the day after we...
Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D
Unique pet-friendly waterfront home in Historic Goodland w/ dock & kayaks
9.2 out of 10, Wonderful, (15)
"We had a large group of college friends stay here for a long weekend and it was exactly what we needed! Plenty of beds, large outdoor space, towels/showers. Also, walking distance to Stan's on Sundays and a short drive over to Marco Island. Would stay here again!"
Unique pet-friendly waterfront home in Historic Goodland w/ dock & kayaks
Naples Studio w/ Community Pool & Tennis Courts!
10.0 out of 10, Exceptional, (1)
"This place was so nice, my favorite on this trip we stayed at, everyone was so friendly "
Naples Studio w/ Community Pool & Tennis Courts!
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See all available properties in Chokoloskee
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.

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, (47)
"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, (117)
"Wanted to bring the family down to experience the wilds of the Everglades and spend some time in a part of Florida that hadn’t been turned into a tourist trap. Chokoloskee and Big Blue came through spectacularly. The natural beauty and experiences here are something that will always stick with us. The host Walter was top notch in offering ideas of places to go and things to see, great in communicating with us. We had a snag with our plans on staying elsewhere the night before we were supposed...
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, (34)
"Awesome place, very clean and well equipped. Probably the nicest and most accommodating hosts we have experienced so far We definitely plan to be back"
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.

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Frequently asked questions

Can I find vacation rentals in Chokoloskee?

Yes, there are vacation rentals close to the most popular attractions in Chokoloskee, or you can choose a more secluded option if you're looking for relaxation. Chokoloskee is known for its waterfront and seafood restaurants.

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

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

How many vacation rentals are there in Chokoloskee?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

While you're exploring the area, Everglades National Park and Chokoloskee Bay are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Gulf Coast Visitor Center and Museum of the Everglades.

What are vacation rentals like in Chokoloskee?

Vacation rentals are private accommodations you can reserve for a short or long stay in Chokoloskee. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.

Recent reviews of Chokoloskee properties
Expedia verified reviews