House
10.0(60 Reviews)
1 Bedroom
4 Guests
Child Friendly
US $316/Night
7 Nights - US $2,215
Chokoloskee Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Chokoloskee
10.0
Apartment
9.5(2 Reviews)
3 Bedrooms
4 Guests
Parking
Internet
Accessibility
Security/Safety
US $235/Night
7 Nights - US $1,645
House
9.4(112 Reviews)
1 Bedroom
Kitchen
Air Conditioner
Pet Friendly- Child Friendly
US $201/Night
7 Nights - US $1,407
House
10.0(54 Reviews)
2 Bedrooms
4 Guests
- Child Friendly
US $325/Night
7 Nights - US $2,274
House
8.3(3 Reviews)
1 Bedroom
4 Guests
- Parking
View- Internet
- Security/Safety
US $283/Night
7 Nights - US $1,983
House
10.0(53 Reviews)
2 Bedrooms
6 Guests
Oceanfront- Parking
Ocean View
Balcony/Terrace
US $364/Night
7 Nights - US $2,549
House
7.0(7 Reviews)
1 Bedroom
4 Guests
- Parking
Pool- Internet
- Pet Friendly
US $123/Night
7 Nights - US $861
Cottage
10.0(21 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $344/Night
7 Nights - US $2,405
Other
8.6(33 Reviews)
12 Bedrooms
37 Guests
- Oceanfront
Breakfast- Parking
- Pool
US $224/Night
7 Nights - US $1,571
Condo
10.0(8 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $147/Night
7 Nights - US $1,031
Condo
10.0(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $195/Night
7 Nights - US $1,362
House
10.0(3 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $318/Night
7 Nights - US $2,225
House
9.8(65 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $529/Night
7 Nights - US $3,703
Cottage
9.8(53 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,396
House
9.8(21 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $479/Night
7 Nights - US $3,350
House
9.6(11 Reviews)
1 Bedroom
3 Guests
- Child Friendly
US $273/Night
7 Nights - US $1,908
House
9.4(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $308/Night
7 Nights - US $2,159
Cabin
8.6(22 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $351/Night
7 Nights - US $2,455
House
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
Laundry
US $423/Night
7 Nights - US $2,958
House
10.0(23 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $228/Night
7 Nights - US $1,595
House
10.0(14 Reviews)
3 Bedrooms
5 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $524/Night
7 Nights - US $3,665
House
10.0(7 Reviews)
4 Bedrooms
8 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $508/Night
7 Nights - US $3,553
House
9.8(41 Reviews)
3 Bedrooms
6 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $387/Night
7 Nights - US $2,708
House
9.6(136 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
7 Nights - US $2,333
House
9.6(22 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $272/Night
7 Nights - US $1,905
House
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $290/Night
7 Nights - US $2,028
Cottage
10.0(14 Reviews)
4 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
Spa
US $455/Night
7 Nights - US $3,186
Condo
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $205/Night
7 Nights - US $1,436
Apartment
9.8(7 Reviews)
1 Bedroom
4 Guests
- Breakfast
- Parking
- Pool
- Spa
US $169/Night
7 Nights - US $1,186
House
9.0(10 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $225/Night
7 Nights - US $1,577
Cabin
8.6(4 Reviews)
1 Bedroom
2 Guests
- Breakfast
- Parking
- Pool
- Spa
US $168/Night
7 Nights - US $1,177
Cabin
8.2(37 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $109/Night
7 Nights - US $763
Apartment
8.2(33 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $129/Night
7 Nights - US $903
House
4.0(1 Review)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
TV
US $125/Night
7 Nights - US $875
Apartment
3 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $361/Night
7 Nights - US $2,527
House
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $826
Cabin
7.4(15 Reviews)
1 Bedroom
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $181/Night
7 Nights - US $1,269
House
1 Bedroom
3 Guests
- Air Conditioner
- Child Friendly
- Laundry
Bedding/Linens
US $150/Night
7 Nights - US $1,050
About Casai's Private Villas and Holiday Rentals in Chokoloskee
Discover more than 38 vacation rentals available in Chokoloskee. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chokoloskee.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chokoloskee, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chokoloskee. On average, places to stay near Chokoloskee offer 436.88 ft², with nightly prices averaging US $278.
With Casai, finding and comparing holiday rentals in Chokoloskee is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 38 Chokoloskee, FL Vacation Rentals
- Prices for a holiday home in Chokoloskee start at US $123
- Top rated vacation home in Chokoloskee is Chokoloskee Dockside “end of the road” (Includes boat slip) with this rental
- Most popular short term in Chokoloskee is Everglades Chokoloskee 3 bdrm Home w/dock, marina, National Park,10,000 Islands
- Cheapest place to stay in Chokoloskee is Everglades City Cabin with Boat Slip and Pool Access!
- Most expensive holiday rental in Chokoloskee is Deep Water Access with a Panoramic View of Chokoloskee Bay
Recently Booked Hotels, Resorts, or Rentals in Chokoloskee
Frequently Asked Questions About Chokoloskee?
What are the top holiday rentals in Chokoloskee?
With numerous options available in Chokoloskee, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chokoloskee:
- Chokoloskee Dockside “end of the road” (Includes boat slip) with this rental
- Waterfront 2 bedroom 1 bath with boat slip
- Chucka Charmer Boat slip included. Chokoloskee
- 3/2 House nestled in the Everglades National Park
- Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
- The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
- A little fishing town Best kept secret in SW Florida
- Chokoloskee-incredible fishing while enjoying Florida with friends and family.
- Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft
- Amazing little fishing cabin on the water with a boat ramp in Everglades City
How many Casai.nz holiday rentals are available in Chokoloskee?
As of 2026, Casai boasts over 38 properties listed in the Chokoloskee area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chokoloskee.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Big Cypress Vacation Rentals in Naples, Florida | 477 |
