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

1. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (297 reviews)
"Great stay!"
United States
Quentin
The price is CA $318
CA $363 total
includes taxes & fees
Aug 13 - Aug 14
River Wilderness Waterfront Cabins

2. Amazing little fishing cabin on the water with a boat ramp in Everglades City

Amazing little fishing cabin on the water with a boat ramp in Everglades City
Everglades City
10.0 out of 10, Exceptional, (2 reviews)
"Cabin is well-maintained and location is quiet. Convenient to many activities. Roomy interior with many amenities."
United States
suzanne c.
The price is CA $191
CA $411 total
includes taxes & fees
Aug 19 - Aug 20
Amazing little fishing cabin on the water with a boat ramp in Everglades City

3. 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 $307
CA $520 total
includes taxes & fees
Aug 23 - Aug 24
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

4. If you prefer wildlife over nightlife this is the place for you, Fakahatchee!

If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
Copeland
10.0 out of 10, Exceptional, (5 reviews)
"Great clean, cute place! Super clean. Very comfortable beds with a variety of pillows to choose so you can get the one that is just right! Love the location by Fakahatchee Strand. Interesting books and a fun (but challenging) puzzle. We had a wonderful time!"
United States
Lisa S.
The price is CA $209
CA $478 total
includes taxes & fees
Aug 13 - Aug 14
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!

5. 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 $92
CA $246 total
includes taxes & fees
Aug 12 - Aug 13
Near the Everglades: Studio at Port of the Islands

6. Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (25 reviews)
"The host is amazing and very helpful. I messaged a lot and she always replied and was very nice. Will definitely book again"
United States
glynn l.
The price is CA $139
CA $348 total
includes taxes & fees
Aug 29 - Aug 30
Naples Marina Getaway Studio DIRECT WATER VIEWS!

7. Naples Resort Retreat w/ Pool Access!

Naples Resort Retreat w/ Pool Access!
Naples
6.6 out of 10, (4 reviews)
"Great potential needs work no bar restaurants as advertised "
United States
Mike S.
The price is CA $81
CA $234 total
includes taxes & fees
Aug 25 - Aug 26
Naples Resort Retreat w/ Pool Access!

8. 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 $86
CA $240 total
includes taxes & fees
Aug 12 - Aug 13
POI Resort Studio Near Everglades NP: Swim + Sail

9. Sunrise Waterfront Cottage

Sunrise Waterfront Cottage
Marco Island
10.0 out of 10, Exceptional, (48 reviews)
"Nice place"
United States
samuel W
The price is CA $244
CA $523 total
includes taxes & fees
Aug 13 - Aug 14
Sunrise Waterfront Cottage

10. Dock, Pool & Tennis Courts: Naples Resort Retreat!

Dock, Pool & Tennis Courts: Naples Resort Retreat!
Naples
6.0 out of 10, (2 reviews)
"Super cute and updated. Pool was great. Short walk to beach. "
United States
Christy R.
The price is CA $109
CA $265 total
includes taxes & fees
Aug 12 - Aug 13
Dock, Pool & Tennis Courts: Naples Resort Retreat!

11. 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 $86
CA $240 total
includes taxes & fees
Aug 12 - Aug 13
Everglades Escape w/ Outdoor Pool & Marina Access!

12. Everglades Studio w/ Resort Amenities & Porch!

Everglades Studio 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 $109
CA $265 total
includes taxes & fees
Aug 12 - Aug 13
Everglades Studio w/ Resort Amenities & Porch!

13. Waterfront 3-BR, 2-BA Pet Friendly Vacation Rental 5 mi to Marco Island

Waterfront 3-BR, 2-BA Pet Friendly Vacation Rental 5 mi to Marco Island
Marco Island
The price is CA $352
CA $878 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront 3-BR, 2-BA Pet Friendly Vacation Rental 5 mi to Marco Island

14. Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is CA $86
CA $240 total
includes taxes & fees
Aug 12 - Aug 13
Everglades Getaway 15 Mi to NP: Sail + Swim!

15. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is CA $86
CA $240 total
includes taxes & fees
Aug 12 - Aug 13
Pool Access: Everglades Resort Retreat!

16. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is CA $86
CA $240 total
includes taxes & fees
Aug 12 - Aug 13
Exclusive 10,000 Islands Access: Naples Studio

17. Resort-Style Naples Studio w/ Marina Access!

Resort-Style Naples Studio w/ Marina Access!
Naples
The price is CA $109
CA $265 total
includes taxes & fees
Aug 12 - Aug 13
Resort-Style Naples Studio w/ Marina Access!

18. 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 $107
CA $263 total
includes taxes & fees
Aug 12 - Aug 13
Resort-Style Studio 15 Mi to Everglades NP

19. 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 $109
CA $265 total
includes taxes & fees
Aug 12 - Aug 13
Bring Your Boat: Condo w/ Pool in Naples!
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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