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Chokoloskee Island Vacation Rentals

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Vacation Rentals in Chokoloskee Island

Deep Water Access with a Panoramic View of Chokoloskee Bay
Property grounds
Deep Water Access with a Panoramic View of Chokoloskee Bay
10.0 out of 10, Exceptional, 47 reviews
"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
Fridge, microwave, oven, stovetop
Waterfront 2 bedroom 1 bath with boat slip
10.0 out of 10, Exceptional, 34 reviews
"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
Property grounds
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
9.6 out of 10, Exceptional, 117 reviews
"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.
Fridge, microwave, oven, stovetop
Two bedroom home fully furnished.
10.0 out of 10, Exceptional, 3 reviews
"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.
Outdoor dining
Chokoloskee-incredible fishing while enjoying Florida with friends and family.
10.0 out of 10, Exceptional, 1 review
"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
Fridge, microwave, oven, stovetop
Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft
10.0 out of 10, Exceptional, 5 reviews
"Everything was perfect!!!!"
Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft
River Wilderness Waterfront Cabins
Lake
River Wilderness Waterfront Cabins
2.5 star property
8.4 out of 10, Very Good, 241 reviews
"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 $200
$228 total
includes taxes & fees
Jun 6 - Jun 7
River Wilderness Waterfront Cabins
4-bedroom house with pool steps from the dock!
Property grounds
4-bedroom house with pool steps from the dock!
9.8 out of 10, Exceptional, 29 reviews
"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!
Pool
Port of The Islands Naples Marina getaway!
9.6 out of 10, Exceptional, 10 reviews
"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 $120
$293 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
Dining
Waterfront dog-friendly home with kayaks, washer/dryer & fast WiFi
8.6 out of 10, Excellent, 8 reviews
"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
Marina
Wood cabin with private dock
9.0 out of 10, Wonderful, 6 reviews
"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 $110
$236 total
includes taxes & fees
Jun 13 - Jun 14
Wood cabin with private dock
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
Property grounds
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
10.0 out of 10, Exceptional, 62 reviews
"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!
Pool
Extreme Naples Charters- "Comfort Zone"-Social Distancing at it's Best!
9.8 out of 10, Exceptional, 19 reviews
"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!
Pool
Marina Fish- Boat and Relax in this Paradise in Naples, Florida!
9.6 out of 10, Exceptional, 4 reviews
"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 $100
$268 total
includes taxes & fees
Jun 6 - Jun 7
Marina Fish- Boat and Relax in this Paradise in Naples, Florida!
Perfect Florida Cottage
Beach nearby, beach towels
Perfect Florida Cottage
9.8 out of 10, Exceptional, 43 reviews
"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
Interior
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
Interior
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
Property grounds
Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D
7.0 out of 10, Good, 7 reviews
"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
Fridge, microwave, oven, stovetop
Unique pet-friendly waterfront home in Historic Goodland w/ dock & kayaks
9.2 out of 10, Wonderful, 15 reviews
"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!
Pool
Naples Studio w/ Community Pool & Tennis Courts!
10.0 out of 10, Exceptional, 1 review
"This place was so nice, my favorite on this trip we stayed at, everyone was so friendly "
Naples Studio w/ Community Pool & Tennis Courts!
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.

Chokoloskee Island Vacation Rental Travel Info

Popular accommodation
Chokoloskee Island private vacation homes
International airport
Miami, FL (MIA-Miami Intl.)

Other types of properties in Chokoloskee Island you may be interested in

Deep Water Access with a Panoramic View of Chokoloskee Bay
Property grounds
Deep Water Access with a Panoramic View of Chokoloskee Bay
10.0 out of 10, Exceptional, 47 reviews
"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
Property grounds
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
9.6 out of 10, Exceptional, 117 reviews
"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
Fridge, microwave, oven, stovetop
Waterfront 2 bedroom 1 bath with boat slip
10.0 out of 10, Exceptional, 34 reviews
"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.

Everything you need to know about Chokoloskee Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chokoloskee Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chokoloskee Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chokoloskee Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $100 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chokoloskee Island rentals

At Expedia, we put the best Chokoloskee Island vacation 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 vacation.

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.

Recent reviews of Chokoloskee Island properties
Expedia verified reviews

Ivey House Everglades Adventures Hotel

Ivey House Everglades Adventures Hotel

5/5 Excellent
Great Stay .....
"Very clean and comfortable. It was made even better by having a wonderful pizza restaurant right down the street. Wildman's Pizza, Pasta and Python. Yum !!!"
A verified traveler stayed at Ivey House Everglades Adventures Hotel
Posted 1 day ago
Ivey House Everglades Adventures Hotel