Vacation rentals in Chokoloskee Island

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Top-rated vacation rentals in Chokoloskee Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Vacation home in Bonita Springs

4.81 out of 5 average rating, 104 reviews

Amazing home w canal views, a mile from the beach!

New&Amazing location Walk or bike riding distance from the best escape to the most beautiful beach locations in Southwest Florida . This 1-bedroom, 2-bed and fold up bed spacious home has an open floor to allow the family to enjoy time away from home. The porch has seating to watch the sunsets with canal views. Step outside to relax play board games or just enjoy the fireplace while you chat with the family. This great place with lots of room for fun. Short distance to Fort Myers, Naples.Miami2

Aug 25 – Sep 1

R2,223 ZAR per night
Guest favorite

Guest suite in Naples

5.0 out of 5 average rating, 131 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Nov 6 – 13

R3,267 ZAR per night
Superhost

Guesthouse in Naples

4.81 out of 5 average rating, 294 reviews

Waterfront Sea Cottage

*Newly rebuilt after Hurricane Ian. Expect some construction within the main home. Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

Sep 16 – 23

R1,807 ZAR per night

Popular amenities for Chokoloskee Island vacation rentals

Other great vacation rentals in Chokoloskee Island

Guest favorite

Cabin in Bonita Springs

4.91 out of 5 average rating, 274 reviews

Calming, relaxing cabin on the Imperial River

May 30 – Jun 6

R1,936 ZAR per night
Guest favorite

Guest suite in Naples

4.87 out of 5 average rating, 158 reviews

Private 2 bedroom/ 2 bathroom living room/ ktchen

Nov 8 – 15

R1,437 ZAR per night
Guest favorite

Condo in Marco Island

4.93 out of 5 average rating, 119 reviews

Marco Beach Ocean Resort 707

Oct 22 – 29

R7,233 ZAR per night
Guest favorite

Apartment in Marco Island

4.94 out of 5 average rating, 219 reviews

Best JW Marriott Alternative Prime~ Location~Pool

Jul 27 – Aug 3

R4,299 ZAR per night
Guest favorite

Farm stay in Naples

4.85 out of 5 average rating, 113 reviews

Happy Little Camper on Modern Farm #4

Jan 3 – 10

R2,112 ZAR per night
Guest favorite

Apartment in Naples

4.92 out of 5 average rating, 123 reviews

Alana’s apartment The Estates of Naples,Florida

Jan 26 – Feb 2

R1,956 ZAR per night
Guest favorite

Guest suite in Naples

4.92 out of 5 average rating, 257 reviews

Garden Studio Just minutes to Naples Sandy Beaches

May 27 – Jun 3

R2,622 ZAR per night
Guest favorite

Bungalow in Naples

4.88 out of 5 average rating, 347 reviews

Private Cozy Coastal Bugalow

May 24 – 31

R1,933 ZAR per night
Guest favorite

Home in Naples

5.0 out of 5 average rating, 120 reviews

Peaceful Gulf Access, Kayaks, Bikes, ebikes

Dec 1 – 8

R3,723 ZAR per night
Guest favorite

Home in Chokoloskee

5.0 out of 5 average rating, 30 reviews

Chokoloskee/Everglades City

May 22 – 29

R5,182 ZAR per night
Guest favorite

Home in Chokoloskee

5.0 out of 5 average rating, 54 reviews

The Reel'em Inn, Chokoloskee Island Paradise

Aug 22 – 29

R7,082 ZAR per night
Guest favorite

Home in Everglades City

5.0 out of 5 average rating, 35 reviews

3/2 House nestled in the Everglades National Park

Dec 13 – 20

R3,945 ZAR per night

Destinations to explore