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

Full 3-bedroom Canal Front home, in Goodland Fl

Full 3-bedroom Canal Front home, in Goodland Fl

Marco Island
Located in Goodland, this vacation home is within a 15-minute walk of Rookery Bay National Estuarine Research Reserve and Goodland Boating Park.
Full 3-bedroom Canal Front home, in Goodland Fl
4-bedroom house with pool steps from the dock!

4-bedroom house with pool steps from the dock!

Everglades City
With a stay at this vacation home in Everglades City, you'll be on the waterfront, within a 5-minute drive of Everglades National Park and Everglades City ...
4-bedroom house with pool steps from the dock!
Waterfront home with kayaks, washer/dryer & fast WiFi

Waterfront home with kayaks, washer/dryer & fast WiFi

Goodland
With a stay at this vacation home in Goodland, you'll be on the waterfront, just a 2-minute walk from Rookery Bay National Estuarine Research Reserve and 8 minutes ...
Waterfront home with kayaks, washer/dryer & fast WiFi
Save an average of 15% on thousands of hotels when you're signed in
The Everglades House

The Everglades House

Ochopee
With a stay at this vacation home in Everglades City, you'll be within a 5-minute drive of Everglades National Park and Everglades City Hall.
The Everglades House
Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ

Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ

Naples
Located in Naples, this vacation home is on the waterfront, within a 5-minute drive of Marsh Trail Trailhead and Rookery Bay Reserve Lands.
Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ
Explore the Everglades!

Explore the Everglades!

Everglades City
With a stay at this vacation home in Everglades City, you'll be within a 5-minute drive of Everglades National Park and Everglades City Hall.
Explore the Everglades!
Catch the Last Big Fish of 2024 — Easy Access to the Water & Holiday Fun!

Catch the Last Big Fish of 2024 — Easy Access to the Water & Holiday Fun!

2 out of 5
Ochopee
With a stay at this vacation home in Chokoloskee, you'll be on the waterfront, within a 5-minute drive of Everglades National Park and Gulf Coast Visitor ...
Catch the Last Big Fish of 2024 — Easy Access to the Water & Holiday Fun!
Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee
With a stay at this vacation home in Chokoloskee, you'll be on the beach, within a 5-minute drive of Everglades National Park and Chokoloskee Bay.
Deep Water Access with a Panoramic View of Chokoloskee Bay
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

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

Goodland
A stay at this vacation home places you in the heart of Goodland, within a 5-minute walk of Rookery Bay National Estuarine Research Reserve and Goodland Boating ...
Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing
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
67 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Full 3-bedroom Canal Front home, in Goodland Fl, 4-bedroom house with pool steps from the dock!, Waterfront home with kayaks, washer/dryer & fast WiFi, The Everglades House, Splendid studio with heated pool, game room, tennis, restaurant, sauna, gym, BBQ, Explore the Everglades!, Catch the Last Big Fish of 2024 — Easy Access to the Water & Holiday Fun!, Deep Water Access with a Panoramic View of Chokoloskee Bay, Home With Cottage Feel Offering Golf Cart, Kayaks, Bikes, Fishing

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
With a stay at this vacation home in Chokoloskee, you'll be on the beach, within a 5-minute drive of Everglades National Park and Chokoloskee Bay.
Deep Water Access with a Panoramic View of Chokoloskee Bay
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
With a stay at Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands in Chokoloskee, you'll be by the sea, within a 5-minute drive ...
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee
With a stay at Waterfront 2 bedroom 1 bath with boat slip in Chokoloskee, you'll be within a 5-minute drive of Everglades National Park and Chokoloskee Bay.
Waterfront 2 bedroom 1 bath with boat slip
Save an average of 15% on thousands of hotels when you're signed in
Chokoloskee-incredible fishing while enjoying Florida with friends and family.

Chokoloskee-incredible fishing while enjoying Florida with friends and family.

Ochopee
With a stay at this vacation home in Chokoloskee, you'll be within a 5-minute drive of Everglades National Park and Chokoloskee Bay.
Chokoloskee-incredible fishing while enjoying Florida with friends and family.
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.