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Chokoloskee Island Holiday Rentals

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Holiday Rentals in Chokoloskee Island

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
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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 NZ$371
includes taxes & fees
17 Jun - 18 Jun
River Wilderness Waterfront Cabins
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!
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 NZ$477
includes taxes & fees
17 Jun - 18 Jun
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
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
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 NZ$384
includes taxes & fees
18 Jun - 19 Jun
Wood cabin with private dock
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 NZ$436
includes taxes & fees
17 Jun - 18 Jun
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
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!
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
Don't see what you're looking for?
See all available properties in Chokoloskee Island
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 Island 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chokoloskee Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chokoloskee Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chokoloskee Island. Seeing all the best attractions is bound to make you fall in love with Chokoloskee Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chokoloskee Island short-term rentals, that won’t be hard to do.

Recent reviews of Chokoloskee Island properties
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