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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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chokoloskee Island vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a glass dining table.

1. 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)
$423 nightly
The price is $464
Oct 1 - Oct 2
Total with taxes and fees
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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, (3 reviews)
"We had a fabulous stay."
United States
Christie
$268 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Amazing little fishing cabin on the water with a boat ramp in Everglades City
A wooden deck with outdoor seating and a grill, surrounded by trees and a body of water.

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
$338 nightly
The price is $371
Oct 7 - Oct 8
Total with taxes and fees
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
A wooden deck with a glass door leading to a balcony overlooking a body of water.

4. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.8 out of 10, Excellent, (299 reviews)
"Great stay!"
United States
Quentin
$235 nightly
The price is $260
Oct 1 - Oct 2
Total with taxes and fees
River Wilderness Waterfront Cabins
A modern living room with a sofa, armchair, and ottoman, a kitchen area with bar stools, and a ceiling fan.

5. 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.
$367 nightly
The price is $403
Oct 2 - Oct 3
Total with taxes and fees
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
A double room with two wooden headboards, a nightstand with a lamp, and a bed with a beige blanket.

6. Bring Your Boat: Condo w/ Pool in Naples!

Bring Your Boat: Condo w/ Pool in Naples!
3.0 star property
Naples
$170 nightly
The price is $189
Oct 1 - Oct 2
Total with taxes and fees
Bring Your Boat: Condo w/ Pool in Naples!
A spacious living area with wicker furniture, a fireplace, and a staircase.

7. 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.
$209 nightly
The price is $229
Oct 1 - Oct 2
Total with taxes and fees
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
A spacious living area with wicker furniture, a fireplace, and a staircase.

8. 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.
$221 nightly
The price is $242
Oct 1 - Oct 2
Total with taxes and fees
Naples Marina Getaway Studio DIRECT WATER VIEWS!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

9. 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.
$173 nightly
The price is $190
Oct 1 - Oct 2
Total with taxes and fees
Everglades Studio w/ Resort Amenities & Porch!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

10. 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.
$173 nightly
The price is $190
Oct 1 - Oct 2
Total with taxes and fees
Naples Resort Retreat w/ Pool Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

11. 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.
$173 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
Dock, Pool & Tennis Courts: Naples Resort Retreat!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

12. 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.
$157 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
Everglades Escape w/ Outdoor Pool & Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

13. 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.
$172 nightly
The price is $189
Oct 1 - Oct 2
Total with taxes and fees
Near the Everglades: Studio at Port of the Islands
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

14. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
$157 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
Exclusive 10,000 Islands Access: Naples Studio
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

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

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
$157 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
Everglades Getaway 15 Mi to NP: Sail + Swim!
A marina with a white yacht docked, a grassy area in the foreground, and a clear sky with clouds.

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

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
$152 nightly
The price is $169
Oct 1 - Oct 2
Total with taxes and fees
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

17. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
$157 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
Pool Access: Everglades Resort Retreat!
A spacious interior with a high ceiling, multiple levels, and a central staircase.

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.
$157 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

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.
$173 nightly
The price is $190
Oct 1 - Oct 2
Total with taxes and fees
Bring Your Boat: Condo w/ Pool in Naples!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

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.
$172 nightly
The price is $189
Oct 1 - Oct 2
Total with taxes and fees
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 Island Hotel Reviews

Everglades Adventures Hotel Suites by Ivey House

Everglades Adventures Hotel Suites by Ivey House

10/10 Excellent
"AAA PLUS Excellent service 100% recommend I stayed with my husband for Memorial Day"
Angela 1-night trip
Posted 16 hours ago
Everglades Adventures Hotel Suites by Ivey House

Find out more about Chokoloskee Island

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 $189 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.

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