--- title: "Chokoloskee Island Vacation Packages 2026 from $490 | 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: 2026-11-14T20:58:33Z --- ![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 $490 ## 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 waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/a7493794.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A wooden dock extending over calm turquoise water, lined with white railings and palm trees.](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 3 - Feb 7** ### [Creekside Inn + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-03/2027-02-07/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1576773&dealMarker=&paandie=true&cabinClass=e) Tavernier 4 nights **7.8/10** \- Good (1,023 reviews) "The staff was friendly and welcoming and the restaurants were very close. On the 2nd day I needed a fresh set of towels and they delivered them quickly. I will stay there again if I'm in Tavanier." Reviewed November 13, 2026 Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop Save 100% on your flight [~~$927~~](https://www.expedia.com/) **$490** 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) **Jan 3 - Jan 7** ### [The Retreat Collection at 1 Hotel & Homes South Beach + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-03/2027-01-07/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&dealMarker=&paandie=true&cabinClass=e) South Beach 4 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 - MIA • Nonstop FLL - BOS • Nonstop [~~$33,123~~](https://www.expedia.com/) **$15,625** per traveler found 2 days ago - ![A beach with rows of sun loungers and umbrellas, a lifeguard tower, and the ocean in the background.](https://images.trvl-media.com/lodging/13000000/12630000/12621700/12621689/8d5053e8.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A multi-story building with a pink and white facade, a visible entrance, and a sign reading 'HEÑROSA'.](https://images.trvl-media.com/lodging/13000000/12630000/12621700/12621689/0d1b46cc.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 26 - Jan 30** ### [Henrosa Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-26/2027-01-30/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12621689&dealMarker=&paandie=true&cabinClass=e) South Beach 4 nights **8.4/10** \- Very good (964 reviews) "There was a lot of very early morning noise in the halls, but other than that, there was very little to complain about! We plan to stay here again if we come back in the future!" Reviewed November 13, 2026 Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$979~~](https://www.expedia.com/) **$497** per traveler found 1 day ago - ![A swimming pool with lounge chairs and a cityscape mural in the background.](https://images.trvl-media.com/lodging/71000000/70330000/70326300/70326285/a5a936f1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A large cruise ship docked at a port with multiple terminals and a bridge in the background.](https://images.trvl-media.com/lodging/71000000/70330000/70326300/70326285/2aae816e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 3 - Feb 7** ### [YotelPad Miami + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-03/2027-02-07/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=70326285&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 4 nights **8.4/10** \- Very good (560 reviews) Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop Save 100% on your flight [~~$1,421~~](https://www.expedia.com/) **$754** per traveler found 1 day ago - ![A spacious lobby with a wooden bench, a sofa, and a round coffee table. There are multiple chairs and tables arranged around the room.](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/0580d913.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern hotel room with a large bed, a desk with a flat-screen TV, a glass partition, and a view of the outdoors.](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/5a873fda.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 3 - Feb 7** ### [President Hotel Villa + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-03/2027-02-07/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=10612810&dealMarker=&paandie=true&cabinClass=e) South Beach 4 nights **8.2/10** \- Very good (1,004 reviews) "They charge a resort fee but don't have any amenities included which justify the fee. Breakfast is no longer included despite being on my reservation. The staff were fine but not very friendly and there is always a wait at the front desk. There was no hot water in the shower of my room too. You also definitely don't want to be on the first floor if you are a light sleeper because there is a lot of noise from the front door and elevator. Lastly, you will need to request for your room to be..." Reviewed November 13, 2026 Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$1,058~~](https://www.expedia.com/) **$569** 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, 819 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, 1003 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 15 - Nov 16, 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 ### [Exclusive 10,000 Islands Access: Naples Studio](https://www.expedia.com/Naples-Hotels-15-Mi-To-Everglades-NP-Studio-W-Marina-Access.h119199523.Hotel-Information) ![A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199523/6c0a7e59.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 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. 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[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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