--- title: "Chokoloskee Island Vacation Packages 2026 from $800 | Expedia" description: "Bundle Chokoloskee Island flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Chokoloskee-Island.d553248635976468286.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-13T11:27:06Z --- ![A night sky with the Milky Way over a calm body of water and a rocky shoreline with wooden posts.](https://images.trvl-media.com/place/3000430940/6a686070-6a7c-41a9-b800-f0b3cf385f24.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Noel Benadom # Chokoloskee Island Vacations from $800 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## The Latest Chokoloskee Island Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A modern living room with a sectional sofa, a round coffee table, and a large window offering a city view.](https://images.trvl-media.com/lodging/137000000/136010000/136001300/136001274/43148bcb.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A spacious balcony with a dining table and chairs, a sofa, and a view of a cityscape and water.](https://images.trvl-media.com/lodging/137000000/136010000/136001300/136001274/e50e6a54.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [501 First Studio Balcony by Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=136001274&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$1,612~~](https://www.expedia.com/) **$800** per traveler found 1 day ago - ![A poolside area with lounge chairs and a view of the ocean at sunset.](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/8e6798dd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An outdoor seating area with tables and chairs under a canopy, surrounded by palm trees.](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/22b95ed1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 27 - Jan 2** ### [The Retreat Collection at 1 Hotel & Homes South Beach + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-27/2027-01-02/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&dealMarker=&paandie=true&cabinClass=e) South Beach 6 nights **8.0/10** \- Very good (1 review) "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...." Reviewed June 22, 2016 Roundtrip • Boston (BOS) - Miami (MIA) BOS - FLL • Nonstop MIA - BOS • 1 stop [~~$49,695~~](https://www.expedia.com/) **$24,399** per traveler found 1 day ago - ![A balcony with a city view, a table with a champagne bottle, and a chair.](https://images.trvl-media.com/lodging/133000000/132830000/132825000/132824939/w1024h767x0y1-2187af23.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A swimming pool with a couple sitting on the edge, surrounded by palm trees and modern buildings in the background.](https://images.trvl-media.com/lodging/133000000/132830000/132825000/132824939/02c5ca78.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 1 - Feb 6** ### [Miami Vacation Rentals Downtown with Pool + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-01/2027-02-06/?FromAirport=EWR&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=132824939&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • New York (EWR) - Miami (MIA) EWR - MIA • Nonstop MIA - EWR • Nonstop [~~$2,237~~](https://www.expedia.com/) **$1,198** per traveler found 18 hours ago - ![A high-rise building with a glass balcony overlooking a cityscape.](https://images.trvl-media.com/lodging/136000000/135380000/135372100/135372016/b6c756f7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A high-rise building with multiple balconies, likely a hotel or residential complex.](https://images.trvl-media.com/lodging/136000000/135380000/135372100/135372016/a8f81a0f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [The Crosby Worldcenter 2BR Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=135372016&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$2,059~~](https://www.expedia.com/) **$1,113** per traveler found 1 day ago - ![A rooftop pool area with a clear view of the city skyline, including a tall building.](https://images.trvl-media.com/lodging/135000000/134330000/134322500/134322401/2e57d61d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern lounge area with a curved white sofa, a round gold table, and a bar area in the background.](https://images.trvl-media.com/lodging/135000000/134330000/134322500/134322401/756ddac7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [The Crosby Balcony 1BR by Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=134322401&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$1,953~~](https://www.expedia.com/) **$1,056** per traveler found 1 day ago ## Discover the most popular places to visit in Chokoloskee Island ### Smallwood Store You can spend time exploring the galleries in Smallwood Store during your trip to Chokoloskee. You can seek out the fishing spots while in the area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=949771102075310080) ## Chokoloskee Island Hotel Deals ### [Everglades Adventures Hotel Suites by Ivey House](https://www.expedia.com/Naples-Hotels-Everglades-Adventures-Hotel-Suites.h57918264.Hotel-Information) ![An indoor swimming pool with a glass ceiling, surrounded by lounge chairs and a white fence.](https://images.trvl-media.com/lodging/58000000/57920000/57918300/57918264/0b5cb125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 107 Camellia St E, Everglades City, FL, 34139, US - Location: 4 mi from Chokoloskee Island - Star rating: 2.5/5 - Guest rating: 9.2/10 (Wonderful, 1000 reviews) - Price: $109 nightly, $121 total, Dec 1 - Dec 2, Total with taxes and fees - Review: Very nice staff. Room was large and we had everything we needed. Would definitely recommend ### [Captain's Table Hotel](https://www.expedia.com/Everglades-City-Hotels-Captains-Table-Hotel.h73778356.Hotel-Information) ![A rectangular swimming pool with a tiled edge, surrounded by a white fence, and shaded by palm trees.](https://images.trvl-media.com/lodging/74000000/73780000/73778400/73778356/c766a001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 202 Broadway Ave E, Everglades City, FL, 34139, US - Location: 3.4 mi from Chokoloskee Island - Star rating: 2.5/5 - Guest rating: 7.8/10 (Good, 818 reviews) - Price: $91 nightly, $101 total, Dec 1 - Dec 2, Total with taxes and fees ### [Ivey House Everglades Adventures Hotel](https://www.expedia.com/Naples-Hotels-Ivey-House-Everglades-Adventures-Hotel.h1796579.Hotel-Information) ![A building with a porch, stairs, and palm trees.](https://images.trvl-media.com/lodging/2000000/1800000/1796600/1796579/92457090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 605 Buckner Ave N, Everglades City, FL, 34139, US - Location: 4 mi from Chokoloskee Island - Star rating: 2/5 - Guest rating: 8.8/10 (Excellent, 1002 reviews) - Price: $109 nightly, $121 total, Nov 30 - Dec 1, Total with taxes and fees - Review: Great stay! ### [Everglades City Motel](https://www.expedia.com/Naples-Hotels-Everglades-City-Motel-Everglades-Adventures-Inn.h16201972.Hotel-Information) ![A modern kitchen with white cabinetry, a marble island, and a glass dining table.](https://images.trvl-media.com/lodging/17000000/16210000/16202000/16201972/b4975d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 309 Collier Ave, Everglades City, FL, 34139, US - Location: 3.7 mi from Chokoloskee Island - Star rating: 2/5 - Guest rating: 8.6/10 (Excellent, 688 reviews) - Price: $109 nightly, $121 total, Nov 15 - Nov 16, Total with taxes and fees - Review: Had a little trouble but they made good on it. ### [Rod And Gun Club](https://www.expedia.com/Naples-Hotels-Rod-And-Gun-Club.h13279263.Hotel-Information) ![A swimming pool with a stone wall and palm trees.](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279263/5bdea26a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 200 Riverside Drive, Everglades City, FL, 34139, US - Location: 3.4 mi from Chokoloskee Island - Star rating: 2/5 - Guest rating: 7.6/10 (Good, 231 reviews) - Price: $179 nightly, $199 total, Nov 14 - Nov 15, Total with taxes and fees ### [River Wilderness Waterfront Cabins](https://www.expedia.com/Naples-Hotels-River-Wilderness-Waterfront-Cabins.h4816075.Hotel-Information) ![A wooden deck with a glass door leading to a balcony overlooking a body of water.](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/b0c661b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 210 Collier Blvd, Everglades City, FL, 34139, US - Location: 3.5 mi from Chokoloskee Island - Star rating: 2.5/5 - Guest rating: 8.6/10 (Excellent, 301 reviews) - Price: $200 nightly, $221 total, Nov 15 - Nov 16, Total with taxes and fees - Review: The cabin was nice but our screen had rips in it so mosquitoes could get in. The biggest issue was the lack of water pressure. You could get a warm shower as long as you didn’t try to use all hot. It was weird. ### [POI Resort Studio Near Everglades NP: Swim + Sail](https://www.expedia.com/Naples-Hotels-POI-Resort-Studio-Near-Everglades-NP-Swim-Sail.h118851159.Hotel-Information) ![A clear swimming pool with lounge chairs and palm trees.](https://images.trvl-media.com/lodging/119000000/118860000/118851200/118851159/a0ed51f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Naples, FL, US - Location: 13.8 mi from Chokoloskee Island - Star rating: 3/5 - Price: $152 nightly, $169 total, Nov 16 - Nov 17, Total with taxes and fees ### [Everglades Getaway 15 Mi to NP: Sail + Swim!](https://www.expedia.com/Naples-Hotels-Everglades-Getaway-15-Mi-To-NP-Sail-Swim.h118851156.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118860000/118851200/118851156/3c918d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Naples, FL, US - Location: 13.8 mi from Chokoloskee Island - Star rating: 3/5 - Price: $152 nightly, $169 total, Nov 15 - Nov 16, Total with taxes and fees 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. [See all properties in Chokoloskee Island](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28®ionId=553248635976468286&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Vacation Rentals](?equalTargetTab=tab-4) - [Things to Do](?equalTargetTab=tab-5) - [Naples Hotels](https://www.expedia.com/Naples-Hotels.d602724.Travel-Guide-Hotels) - [Cabin Rentals in Plantation Island](https://www.expedia.com/Plantation-Island-Cabins.d553248635975847818-aaCabins.Travel-Guide-Accommodation) - [Rv Parks in Ten Thousand Islands](https://www.expedia.com/Ten-Thousand-Islands-RV-Parks.d6216853-aaRVParks.Travel-Guide-Accommodation) - [Fishing Resorts & in Everglades City](https://www.expedia.com/Everglades-City-Hotels-Fishing-Hotels.0-0-d6023564-tFishingHotels.Travel-Guide-Filter-Hotels) - [Houseboats in Ten Thousand Islands](https://www.expedia.com/Ten-Thousand-Islands-Houseboats.d6216853-aaHouseboats.Travel-Guide-Accommodation) - 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[Naples Vacations](https://www.expedia.com/Naples.d602724.Destination-Travel-Guides) - [Visit Everglades City](https://www.expedia.com/Everglades-City.dx6023564) - [Cape Romano](https://www.expedia.com/Cape-Romano-Florida.d6326537.Vacation-Attraction) - [Pa-Hay-Okee Overlook](https://www.expedia.com/Pa-Hay-Okee-Overlook-Florida.d553248621533115733.Vacation-Attraction) - [Copeland Vacations](https://www.expedia.com/Copeland.d3000430951.Destination-Travel-Guides) - [Fort Myers Beach Vacations](https://www.expedia.com/Fort-Myers-Beach.d7194.Destination-Travel-Guides) - [Everglades City Vacations](https://www.expedia.com/Everglades-City.d6023564.Destination-Travel-Guides) - [Gulf Coast Visitor Center](https://www.expedia.com/Gulf-Coast-Visitor-Center-Everglades-City.d6327165.Vacation-Attraction) - [Big Cypress National Preserve](https://www.expedia.com/Big-Cypress-National-Preserve-Florida.d553248621533115741.Vacation-Attraction) - [Visit Naples](https://www.expedia.com/Naples.dx602724) - [Scuba Diving Vacation Packages Chokoloskee Island](https://www.expedia.com/lp/theme-vacations/scuba-diving-vacations/553248635976468286/Chokoloskee-Island) - [Visit Ten Thousand Islands](https://www.expedia.com/Ten-Thousand-Islands.dx6216853) - [Marco Island Vacations](https://www.expedia.com/Marco-Island.d8812.Destination-Travel-Guides) - [Boyne South Golf Course](https://www.expedia.com/Boyne-South-Golf-Course-Naples.d553248621561885030.Vacation-Attraction) - [Museum of the Everglades](https://www.expedia.com/Museum-Of-The-Everglades-Everglades-City.d6183268.Vacation-Attraction) - [Marsh Trail Trailhead](https://www.expedia.com/Marsh-Trail-Trailhead-Naples.d553248635974660969.Vacation-Attraction) - [Eagle Lakes Golf Club](https://www.expedia.com/Eagle-Lakes-Golf-Club-Naples.d6327155.Vacation-Attraction) - [Goodland Vacations](https://www.expedia.com/Goodland.d6177534.Destination-Travel-Guides) - [Everglades City Hall](https://www.expedia.com/Everglades-City-Hall-Everglades-City.d6183278.Vacation-Attraction) - 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