--- 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: 2026-11-13T06:50:11Z --- ![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 14 hours ago - ![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) ![A rooftop pool area with a clear view of the city skyline, including a tall building.](https://images.trvl-media.com/lodging/136000000/135380000/135372100/135372016/33cb632d.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, 1001 reviews) - Price: $109 nightly, $121 total, Nov 30 - Dec 1, Total with taxes and fees - Review: The room was just renovated and was very clean and roomy. The pool was right outside our door. The staff was extremely friendly with suggestions of what to do during our 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 14 - Nov 15, 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) ![A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.](https://images.trvl-media.com/lodging/119000000/118860000/118851200/118851156/90988d8c.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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