A calm lake with a clear sky and scattered clouds, surrounded by dense green forest.

Chokoloskee Vacation Rentals

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Our top choices for Chokoloskee vacation rentals

1. 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, (3 reviews)
"We had a fabulous stay."
United States
Christie
The price is CA $206
CA $410 total
includes taxes & fees
Oct 5 - Oct 6
Amazing little fishing cabin on the water with a boat ramp in Everglades City

2. 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 $280
CA $484 total
includes taxes & fees
Sep 27 - Sep 28
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

3. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (298 reviews)
"Great stay!"
United States
Quentin
The price is CA $322
CA $367 total
includes taxes & fees
Sep 27 - Sep 28
River Wilderness Waterfront Cabins

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 place, the home and the fishing was phenomenal."
United States
Luke W.
The price is CA $282
CA $541 total
includes taxes & fees
Oct 1 - Oct 2
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!

5. Resort-style Naples Studio w/ Marina Access!

Resort-style Naples Studio w/ Marina Access!
3.0 star property
Naples
The price is CA $107
CA $215 total
includes taxes & fees
Sep 30 - Oct 1
Resort-style Naples Studio w/ Marina Access!

6. 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 $82
CA $236 total
includes taxes & fees
Sep 27 - Sep 28
Naples Resort Retreat w/ Pool Access!

7. 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 $134
CA $342 total
includes taxes & fees
Sep 29 - Sep 30
Naples Marina Getaway Studio DIRECT WATER VIEWS!

8. 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 $120
CA $325 total
includes taxes & fees
Oct 1 - Oct 2
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

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

Resort-Style Naples Studio w/ Marina Access!
Naples
The price is CA $69
CA $223 total
includes taxes & fees
Sep 30 - Oct 1
Resort-Style Naples Studio w/ Marina Access!

10. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is CA $87
CA $243 total
includes taxes & fees
Sep 27 - Sep 28
Pool Access: Everglades Resort Retreat!

11. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is CA $87
CA $243 total
includes taxes & fees
Sep 27 - Sep 28
Exclusive 10,000 Islands Access: Naples Studio

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

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is CA $87
CA $243 total
includes taxes & fees
Sep 27 - Sep 28
Everglades Getaway 15 Mi to NP: Sail + Swim!

13. 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 $110
CA $270 total
includes taxes & fees
Sep 27 - Sep 28
Everglades Studio w/ Resort Amenities & Porch!

14. 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 $87
CA $243 total
includes taxes & fees
Sep 27 - Sep 28
Everglades Escape w/ Outdoor Pool & Marina Access!

15. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
The price is CA $128
CA $238 total
includes taxes & fees
Sep 27 - Sep 28
POI Resort Studio Near Everglades NP: Swim + Sail

16. 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 $110
CA $268 total
includes taxes & fees
Sep 29 - Sep 30
Dock, Pool & Tennis Courts: Naples Resort Retreat!

17. 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 $80
CA $235 total
includes taxes & fees
Sep 27 - Sep 28
Bring Your Boat: Condo w/ Pool in Naples!

18. 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 $87
CA $243 total
includes taxes & fees
Sep 27 - Sep 28
POI Resort Studio Near Everglades NP: Swim + Sail

19. Near the Everglades: Studio at Port of the Islands

Near the Everglades: Studio at Port of the Islands
Naples
6.0 out of 10, (2 reviews)
"Very quiet, adjacent to marina with a nice pool. Staff was very friendly and responsive."
United States
Sally G.
The price is CA $93
CA $249 total
includes taxes & fees
Sep 29 - Sep 30
Near the Everglades: Studio at Port of the Islands

20. 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 $78
CA $232 total
includes taxes & fees
Sep 29 - Sep 30
Resort-Style Studio 15 Mi to Everglades NP
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 Hotel Reviews

Find out more about Chokoloskee

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. 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.

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?

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool: This Chokoloskee vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Chokoloskee?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

Big Cypress National Preserve and Everglades National Park are a couple of lovely local spots to get outside and enjoy nature. Chokoloskee Bay and Smallwood Store are other places to visit while you're in town.

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.