Book Holiday Homes in Chokoloskee

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chokoloskee

@cypresscottage

@cypresscottage

Ochopee FL
Stay at this holiday home in Everglades City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Museum of the Everglades and Gulf Coast ...
Opens in a new window@cypresscottage
Waterfront home with kayaks, washer/dryer & fast WiFi

Waterfront home with kayaks, washer/dryer & fast WiFi

Goodland FL
Stay at this holiday home in Goodland. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Goodland Boating Park and Otter Mound ...
Opens in a new windowWaterfront home with kayaks, washer/dryer & fast WiFi
Waterfront house with AC in the Everglades with Large Deck

Waterfront house with AC in the Everglades with Large Deck

Ochopee FL
Stay at this holiday home in Everglades City. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Gulf Coast Visitor Center and Museum of the ...
Opens in a new windowWaterfront house with AC in the Everglades with Large Deck
Save an average of 15% on thousands of hotels when you're signed in
Waterfront retreat with bay views, dog-friendly, & snowbird-ready

Waterfront retreat with bay views, dog-friendly, & snowbird-ready

Goodland FL
Stay at this holiday home in Goodland. Enjoy a garden, laundry facilities and patios. Popular attractions Goodland Boating Park and Otter Mound Preserve are ...
Opens in a new windowWaterfront retreat with bay views, dog-friendly, & snowbird-ready
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 FL
Stay at this holiday home in Naples. Enjoy a garden, laundry facilities and air conditioning. Popular attraction Loop Road is located nearby.
Opens in a new windowIf you prefer wildlife over nightlife this is the place for you, Fakahatchee!
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

Goodland FL
Stay at this holiday home in Goodland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Goodland Boating Park and Otter Mound Preserve ...
Opens in a new windowHome With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
Charming Home Waterfront and Pool.

Charming Home Waterfront and Pool.

Naples FL
Stay at this holiday home in Naples. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Rookery Bay Reserve Lands and Marsh Trail Trailhead are ...
Opens in a new windowCharming Home Waterfront and Pool.
Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
Stay at this beach holiday home in Chokoloskee. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
Opens in a new windowDeep Water Access with a Panoramic View of Chokoloskee Bay
4-bedroom house with pool steps from the dock!

4-bedroom house with pool steps from the dock!

Everglades City FL
Stay at this holiday home in Everglades City. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Museum of the Everglades and Gulf Coast Visitor ...
Opens in a new window4-bedroom house with pool steps from the dock!
Don't see what you're looking for?
See all available properties in Chokoloskee
View all properties
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.

Chokoloskee Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chokoloskee vacation homes are the perfect way for you to wing it.

Holiday houses in Chokoloskee let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chokoloskee in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chokoloskee adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chokoloskee with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chokoloskee vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chokoloskee Holiday Homes essential information

Accommodation
28 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
@cypresscottage, Waterfront home with kayaks, washer/dryer & fast WiFi, Waterfront house with AC in the Everglades with Large Deck, Waterfront retreat with bay views, dog-friendly, & snowbird-ready, If you prefer wildlife over nightlife this is the place for you, Fakahatchee!, Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing, Charming Home Waterfront and Pool., Deep Water Access with a Panoramic View of Chokoloskee Bay, 4-bedroom house with pool steps from the dock!

Top trending hotels in Chokoloskee

Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
Stay at this beach holiday home in Chokoloskee. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
Opens in a new windowDeep Water Access with a Panoramic View of Chokoloskee Bay
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Opens in a new windowWaterfront 2 bedroom 1 bath with boat slip
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL
Enjoy a garden, laundry facilities and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Opens in a new windowEverglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Save an average of 15% on thousands of hotels when you're signed in
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee FL
Enjoy laundry facilities and air conditioning. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Opens in a new windowWaterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
Don't see what you're looking for?
See all available properties in Chokoloskee
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.