Vacation rentals in Chokoloskee Island, FL

Best vacation rentals and Airbnb offers in Chokoloskee Island, FL

Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat

Cottage, Chokoloskee Island

Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat is a cottage in Chokoloskee Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

Read more

About Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat

Stay In Our 10,000 Island Guest Suite For A Special Everglades Retreat is a cottage in Chokoloskee Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,123.

From$160/night

Show›

Everglades City Cabin: Dock & Heated Pool!

Holiday Home, Chokoloskee Island

Everglades City Cabin: Dock & Heated Pool! is a holiday home in Chokoloskee Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Everglades City Cabin: Dock & Heated Pool!

Everglades City Cabin: Dock & Heated Pool! is a holiday home in Chokoloskee Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,000.

From$211/night

Show›

3/2 House nestled in the Everglades National Park

Holiday Home, Chokoloskee Island

3/2 House nestled in the Everglades National Park is a holiday home in Chokoloskee Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 3/2 House nestled in the Everglades National Park

3/2 House nestled in the Everglades National Park is a holiday home in Chokoloskee Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,524.

From$218/night

Show›

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

Cottage, Chokoloskee Island

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck. is a cottage in Chokoloskee Island, with outdoor space, parking, and kitchen access. This stay gives travelers a…

Read more

About Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck. is a cottage in Chokoloskee Island, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,585.

From$226/night

Show›

Waterfront vacation rentals in Chokoloskee Island, FL

Discover vacation rentals close to the coast, water, and beach areas around Chokoloskee Island, FL.

Spectacular Waterfront Home-3 Bed, 2 Bath w/ Pool and Breathtaking Views!

Holiday Home, Chokoloskee Island

Spectacular Waterfront Home-3 Bed, 2 Bath w/ Pool and Breathtaking Views! is a holiday home in Chokoloskee Island, with pool access, easy beach access, and kitchen access. This stay gives…

Read more

About Spectacular Waterfront Home-3 Bed, 2 Bath w/ Pool and Breathtaking Views!

Spectacular Waterfront Home-3 Bed, 2 Bath w/ Pool and Breathtaking Views! is a holiday home in Chokoloskee Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,634.

From$376/night

Show›

Charming Home Waterfront and Pool.

Holiday Home, Chokoloskee Island

Charming Home Waterfront and Pool. is a holiday home in Chokoloskee Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Charming Home Waterfront and Pool.

Charming Home Waterfront and Pool. is a holiday home in Chokoloskee Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,543.

From$506/night

Show›

NEW! Luxury Villa on the Barron River with Resort Amenities

Villa, Chokoloskee Island

NEW! Luxury Villa on the Barron River with Resort Amenities is a villa in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About NEW! Luxury Villa on the Barron River with Resort Amenities

NEW! Luxury Villa on the Barron River with Resort Amenities is a villa in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,195.

From$599/night

Show›

NEW! Luxury Villa on the Barron River with Resort Amenities

Villa, Chokoloskee Island

NEW! Luxury Villa on the Barron River with Resort Amenities is a villa in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About NEW! Luxury Villa on the Barron River with Resort Amenities

NEW! Luxury Villa on the Barron River with Resort Amenities is a villa in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,195.

From$599/night

Show›

Vacation rentals with a pool in Chokoloskee Island, FL

Add a pool to the search when you want an easy place to cool off between outings.

Resort Studio w/ Community Pool in Naples!

Apartment, Chokoloskee Island

Resort Studio w/ Community Pool in Naples! is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Resort Studio w/ Community Pool in Naples!

Resort Studio w/ Community Pool in Naples! is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $951.

From$93/night

Show›

Boat, Bird & Bask: Studio 15 Mi to Everglades NP

Apartment, Chokoloskee Island

Boat, Bird & Bask: Studio 15 Mi to Everglades NP is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Boat, Bird & Bask: Studio 15 Mi to Everglades NP

Boat, Bird & Bask: Studio 15 Mi to Everglades NP is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $967.

From$95/night

Show›

Naples Studio Near Everglades w/ Marina!

Apartment, Chokoloskee Island

Naples Studio Near Everglades w/ Marina! is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Naples Studio Near Everglades w/ Marina!

Naples Studio Near Everglades w/ Marina! is a apartment in Chokoloskee Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,013.

From$101/night

Show›

Naples Resort Retreat w/ Pool Access!

Apartment, Chokoloskee Island

Naples Resort Retreat w/ Pool Access! is a apartment in Chokoloskee Island, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Naples Resort Retreat w/ Pool Access!

Naples Resort Retreat w/ Pool Access! is a apartment in Chokoloskee Island, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,045.

From$105/night

Show›

Vacation rentals with parking in Chokoloskee Island, FL

Find vacation rentals that make arriving by car easier.

Access to 10,000 Islands: Resort-Style Naples Gem!

Apartment, Chokoloskee Island

Access to 10,000 Islands: Resort-Style Naples Gem! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Access to 10,000 Islands: Resort-Style Naples Gem!

Access to 10,000 Islands: Resort-Style Naples Gem! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $757.

From$108/night

Show›

Everglades Getaway 15 Mi to NP: Sail + Swim!

Apartment, Chokoloskee Island

Everglades Getaway 15 Mi to NP: Sail + Swim! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $795.

From$114/night

Show›

Resort-Style Studio 15 Mi to Everglades NP

Apartment, Chokoloskee Island

Resort-Style Studio 15 Mi to Everglades NP is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Resort-Style Studio 15 Mi to Everglades NP

Resort-Style Studio 15 Mi to Everglades NP is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $795.

From$114/night

Show›

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

Holiday Home, Chokoloskee Island

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise is a holiday home in Chokoloskee Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise is a holiday home in Chokoloskee Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,081.

From$440/night

Show›

Pet-friendly vacation rentals in Chokoloskee Island, FL

Bring your pet along with stays that welcome four-legged travelers.

Historic Home in the Heart of Everglades City

Holiday Home, Chokoloskee Island

Historic Home in the Heart of Everglades City is a holiday home in Chokoloskee Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Historic Home in the Heart of Everglades City

Historic Home in the Heart of Everglades City is a holiday home in Chokoloskee Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,855.

From$265/night

Show›

Beautiful Condo in Paradise located in the heart of the Everglades.

Condo, Chokoloskee Island

Beautiful Condo in Paradise located in the heart of the Everglades. is a condo in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About Beautiful Condo in Paradise located in the heart of the Everglades.

Beautiful Condo in Paradise located in the heart of the Everglades. is a condo in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,129.

From$304/night

Show›

Newly Refurbished Home in the middle of Everglades City with Fishing from Dock

Holiday Home, Chokoloskee Island

Newly Refurbished Home in the middle of Everglades City with Fishing from Dock is a holiday home in Chokoloskee Island, with pet-friendly space. This stay gives travelers a comfortable base…

Read more

About Newly Refurbished Home in the middle of Everglades City with Fishing from Dock

Newly Refurbished Home in the middle of Everglades City with Fishing from Dock is a holiday home in Chokoloskee Island, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,461.

From$352/night

Show›

Deep Water Access with a Panoramic View of Chokoloskee Bay

Holiday Home, Chokoloskee Island

Deep Water Access with a Panoramic View of Chokoloskee Bay is a holiday home in Chokoloskee Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

Read more

About Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay is a holiday home in Chokoloskee Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,058.

From$437/night

Show›

Vacation rentals with a kitchen in Chokoloskee Island, FL

Compare stays with kitchen access for longer trips and easier meals.

Near the Everglades: Studio at Port of the Islands

Apartment, Chokoloskee Island

Near the Everglades: Studio at Port of the Islands is a apartment in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Near the Everglades: Studio at Port of the Islands

Near the Everglades: Studio at Port of the Islands is a apartment in Chokoloskee Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $779.

From$111/night

Show›

Pool Access: Everglades Resort Retreat!

Apartment, Chokoloskee Island

Pool Access: Everglades Resort Retreat! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat! is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$114/night

Show›

POI Resort Studio Near Everglades NP: Swim + Sail

Apartment, Chokoloskee Island

POI Resort Studio Near Everglades NP: Swim + Sail is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $806.

From$115/night

Show›

Exclusive 10,000 Islands Access: Naples Studio

Apartment, Chokoloskee Island

Exclusive 10,000 Islands Access: Naples Studio is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio is a apartment in Chokoloskee Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $810.

From$116/night

Show›