A night sky with the Milky Way over a calm body of water and a rocky shoreline with wooden posts.

Chokoloskee Island Vacation Rentals

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Our top choices for Chokoloskee Island vacation rentals

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
Ochopee
9.8 out of 10, Exceptional, (21 reviews)
"Phenomenal place to stay. Enjoyed everyday we were there. "
United States
Devon G.
The price is CA $315
CA $740 total
includes taxes & fees
Jun 29 - Jun 30
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (294 reviews)
"Great stay!"
United States
Quentin
The price is CA $324
CA $369 total
includes taxes & fees
Jun 29 - Jun 30
River Wilderness Waterfront Cabins

Sunrise Waterfront Cottage

Sunrise Waterfront Cottage
Marco Island
10.0 out of 10, Exceptional, (47 reviews)
"Beautiful location on the water and nearby restaurants Bikes and kayaks available Our host was wonderful "
United States
Joseph W.
The price is CA $254
CA $539 total
includes taxes & fees
Jun 27 - Jun 28
Sunrise Waterfront Cottage

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

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
Naples
9.8 out of 10, Exceptional, (11 reviews)
"The host did a great jobThe resort was as advertised"
United States
Skip S.
The price is CA $121
CA $327 total
includes taxes & fees
Jun 29 - Jun 30
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

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

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
Ochopee
10.0 out of 10, Exceptional, (21 reviews)
"Cool place, beautiful inside"
United States
Sarah J
The price is CA $281
CA $493 total
includes taxes & fees
Jun 28 - Jun 29
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is CA $88
CA $241 total
includes taxes & fees
Jun 30 - Jul 1
Pool Access: Everglades Resort Retreat!

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (24 reviews)
"We had a very nice time. The room was clean and comfortable. Beautiful sunrises. The host was friendly and accommodating."
United States
Maryann H.
The price is CA $135
CA $344 total
includes taxes & fees
Jun 29 - Jun 30
Naples Marina Getaway Studio DIRECT WATER VIEWS!

POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
Naples
4.8 out of 10, (3 reviews)
"Room shown was still in use when we arrived then substituted for a non upgraded, dirty room. Heavy chemical cleaner smell, floors, kitchen, and bathroom not clean or anywhere near what was shown in listing pictures. Felt like a bait and switch. Emailed Evolve Travel upon checkout, a formal claim initiated by them. 5 days later still no resolution. "
United States
Liane H.
The price is CA $88
CA $241 total
includes taxes & fees
Jun 28 - Jun 29
POI Resort Studio Near Everglades NP: Swim + Sail

Naples Hideaway w/ Resort Amenities & Porch!

Naples Hideaway w/ Resort Amenities & Porch!
Naples
6.6 out of 10, (4 reviews)
"Nice place to spend for a short stay. Unit not really set up for a long stay."
United States
James L.
The price is CA $111
CA $268 total
includes taxes & fees
Jun 28 - Jun 29
Naples Hideaway w/ Resort Amenities & Porch!

Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is CA $88
CA $241 total
includes taxes & fees
Jul 7 - Jul 8
Everglades Getaway 15 Mi to NP: Sail + Swim!

Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is CA $88
CA $241 total
includes taxes & fees
Jun 29 - Jun 30
Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Condo

Exclusive 10,000 Islands Access: Naples Condo
Naples
2.0 out of 10, (1 review)
"Other guests were in our room when we arrived. Could not reach host with contact information. Property is poorly maintained."
United States
Mark K.
The price is CA $111
CA $268 total
includes taxes & fees
Jun 28 - Jun 29
Exclusive 10,000 Islands Access: Naples Condo

Resort-Style Studio 15 Mi to Everglades NP

Resort-Style Studio 15 Mi to Everglades NP
Naples
7.0 out of 10, Good, (2 reviews)
"The room was not very clean. The price was good but you get what you pay for. I would not stay here again! "
United States
Jodie M.
The price is CA $109
CA $265 total
includes taxes & fees
Jul 8 - Jul 9
Resort-Style Studio 15 Mi to Everglades NP

Bring Your Boat: Condo w/ Pool in Naples!

Bring Your Boat: Condo w/ Pool in Naples!
Naples
4.0 out of 10, (1 review)
"no restaurant open during the week "
United States
Robert S.
The price is CA $111
CA $266 total
includes taxes & fees
Jul 7 - Jul 8
Bring Your Boat: Condo w/ Pool in Naples!

Dock, Pool & Tennis Courts: Naples Resort Retreat!

Dock, Pool & Tennis Courts: Naples Resort Retreat!
Naples
10.0 out of 10, Exceptional, (1 review)
"Super cute and updated. Pool was great. Short walk to beach. "
United States
Christy R.
The price is CA $111
CA $268 total
includes taxes & fees
Jun 29 - Jun 30
Dock, Pool & Tennis Courts: Naples Resort Retreat!

Everglades Escape w/ Outdoor Pool & Marina Access!

Everglades Escape w/ Outdoor Pool & Marina Access!
Naples
8.0 out of 10, Very good, (3 reviews)
"Great Stay!!!"
United States
Ryan S.
The price is CA $88
CA $241 total
includes taxes & fees
Jun 29 - Jun 30
Everglades Escape w/ Outdoor Pool & Marina Access!

Access to 10,000 Islands: Resort-Style Naples Gem!

Access to 10,000 Islands: Resort-Style Naples Gem!
Naples
8.0 out of 10, Very good, (3 reviews)
"The room was clean. The host was responsive. The only downside we found is that it is far away from everything we wanted to do. Great place. "
United States
Vanessa O.
The price is CA $88
CA $241 total
includes taxes & fees
Jun 29 - Jun 30
Access to 10,000 Islands: Resort-Style Naples Gem!

Near the Everglades: Studio at Port of the Islands

Near the Everglades: Studio at Port of the Islands
Naples
10.0 out of 10, Exceptional, (1 review)
"Very quiet, adjacent to marina with a nice pool. Staff was very friendly and responsive."
United States
Sally G.
The price is CA $78
CA $230 total
includes taxes & fees
Jun 29 - Jun 30
Near the Everglades: Studio at Port of the Islands
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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