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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chokoloskee Island vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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, (4 reviews)
"We had a fabulous stay."
United States
Christie
The price is ￥24,898
￥50,401 total
includes taxes & fees
Oct 20 - Oct 21
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.

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 ￥31,300
￥54,471 total
includes taxes & fees
Oct 18 - Oct 19
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.

3. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (301 reviews)
"Staff was accommodating. Perfect setting and location. We are a repeat customer."
United States
Tangela
The price is ￥30,656
￥34,949 total
includes taxes & fees
Oct 18 - Oct 19
River Wilderness Waterfront Cabins
A modern living room with a sofa, armchair, and ottoman, a kitchen area with bar stools, and a ceiling fan.

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 ￥31,616
￥63,667 total
includes taxes & fees
Oct 18 - Oct 19
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
A spacious living area with wicker furniture, a fireplace, and a staircase.

5. 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 ￥13,437
￥36,256 total
includes taxes & fees
Oct 16 - Oct 17
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
A marina with a white yacht docked, a grassy area in the foreground, and a clear sky with clouds.

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

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
The price is ￥14,385
￥26,701 total
includes taxes & fees
Oct 18 - Oct 19
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious living area with wicker furniture, a fireplace, and a staircase.

7. Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (25 reviews)
"Very nice room and property - and affordable! Clean and comfortable."
United States
Vickie W.
The price is ￥15,018
￥38,169 total
includes taxes & fees
Oct 16 - Oct 17
Naples Marina Getaway Studio DIRECT WATER VIEWS!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

8. 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 ￥12,351
￥30,058 total
includes taxes & fees
Oct 18 - Oct 19
Naples Resort Retreat w/ Pool Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

9. 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 ￥12,192
￥29,882 total
includes taxes & fees
Oct 28 - Oct 29
Resort-Style Studio 15 Mi to Everglades NP
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

10. 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 ￥9,817
￥27,245 total
includes taxes & fees
Oct 18 - Oct 19
Everglades Escape w/ Outdoor Pool & Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

11. 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 ￥12,351
￥30,058 total
includes taxes & fees
Oct 18 - Oct 19
Everglades Studio w/ Resort Amenities & Porch!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

12. 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 ￥12,172
￥29,833 total
includes taxes & fees
Oct 16 - Oct 17
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.

13. 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 ￥12,351
￥30,058 total
includes taxes & fees
Oct 28 - Oct 29
Dock, Pool & Tennis Courts: Naples Resort Retreat!
A spacious interior with a high ceiling, multiple levels, and a central staircase.

14. 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 ￥9,817
￥27,245 total
includes taxes & fees
Oct 18 - Oct 19
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

15. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is ￥12,826
￥30,585 total
includes taxes & fees
Oct 28 - Oct 29
Pool Access: Everglades Resort Retreat!
A covered outdoor area with a tiled roof, large windows, and a paved walkway.

16. Everglades Escape w/ Heated Pool & Marina Access!

Everglades Escape w/ Heated Pool & Marina Access!
3.0 star property
Naples
The price is ￥14,385
￥26,701 total
includes taxes & fees
Oct 18 - Oct 19
Everglades Escape w/ Heated Pool & Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

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

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is ￥9,817
￥27,245 total
includes taxes & fees
Oct 28 - Oct 29
Everglades Getaway 15 Mi to NP: Sail + Swim!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

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

Resort-Style Naples Studio w/ Marina Access!
Naples
The price is ￥12,351
￥30,058 total
includes taxes & fees
Oct 28 - Oct 29
Resort-Style Naples Studio w/ Marina Access!
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.
The price is ￥12,330
￥30,008 total
includes taxes & fees
Oct 18 - Oct 19
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. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is ￥9,817
￥27,245 total
includes taxes & fees
Oct 19 - Oct 20
Exclusive 10,000 Islands Access: Naples Studio
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

Captain's Table Hotel

Captain's Table Hotel

8/10 Good
"The Captains Table is an older motel that over all is good. The room access is, however, tricky, as you must park, then walk all around it to enter first floor rooms from outside. The room entry is also tricky, with four steps, then another to get in the room. Coming out you step down and the stairs are right there. Pay attention, or you might fall."
Patricia 1-night trip
Posted 18 hours ago
Captain's Table Hotel

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