
Holiday rentals in Chokoloskee Island
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chokoloskee Island
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chokoloskee Island holiday rentals
Other great holiday rentals in Chokoloskee Island
Guest favourite

Home in Naples
4.96 out of 5 average rating, 67 reviewsBeautiful Naples Retreat
JimmyRating, 5 stars12 months ago
This beautiful home was a great hub for our Naples trip! It was clean, spacious, quiet and the pool, hot tub and rear outdoor lounge area was amazing!! Elena was great to communicate with and made the check in and out a very easy process. I’d highly recommended this beautiful home for your next Naples vacation!
Superhost

Home in Naples
5 out of 5 average rating, 4 reviewsThe Suzana Sunrise- 5 minutes to Vanderbilt Beach!
LynnRating, 5 stars14 months ago
The house is beautifully appointed - great size & immaculately clean . Would definitely return next trip to Naples .
Guest favourite

Villa in Naples
4.97 out of 5 average rating, 30 reviewsNaples Villa Heated Pool 1.3M to beach-11 People
GinaRating, 5 stars2 weeks ago
Highly recommend! We stayed for a week and had a great time. Place was exactly as shown and had everything we needed. Communication with hosts was easy and responsive. Spent lots of time at the pool. We liked the location with easy access to both Clam Pass and Lowdermilk beaches. Recommend catching a sunset. Lots of nearby restaurants and shopping needs. Would definitely go back!
Guest favourite

Home in Naples
4.89 out of 5 average rating, 18 reviewsCasa Del Mar - Golf Lover's Dream!
Mary KateRating, 5 stars1 month ago
Our stay at this beach house was nothing short of exceptional! From the moment we arrived, we were impressed by how well-appointed and immaculately clean the home was. Every detail was thoughtfully curated, making it feel both luxurious and comfortable. The outdoor space was truly the highlight— a beautiful pool, relaxing spa, and a fun putting green that kept everyone entertained. Whether we were soaking up the sun by the pool or unwinding in the spa under the stars, it felt like our private oasis. The beach was just a short walk away, making it easy to enjoy the ocean whenever we wanted. Inside, the home was stylishly furnished with high-end touches and had everything we needed for a stress-free vacation. The kitchen was fully stocked, the bedrooms were cozy, and the living areas were perfect for gathering.
Guest favourite

Home in Naples
4.94 out of 5 average rating, 226 reviewsCathedral Heights
JenniferRating, 5 stars1 month ago
Our family of 8 (adults/adult children) stayed at Chris' home. It was exactly as it was shown in the photos or even better. The lanai area with pool included ample sitting and lounging for all. Very comfy furniture. House is pristine inside with new appliances. House was immaculate upon arrival. Quiet neighborhood and walkable to the beach and many places to eat. Will stay here again.
Guest favourite

Home in Naples
4.94 out of 5 average rating, 87 reviewsKey West home less than 1 mile from the beach
SophieRating, 5 stars2 weeks ago
Our group had a wonderful stay! The house was beautiful, clean and in a great locations. The host was responsive to our questions and gave us great recommendations. 10/10!
Superhost

Apartment in Marco Island
4.86 out of 5 average rating, 21 reviews19 FL Oceanfront Two bed & baths Sunset&Ocean View
AndrewRating, 5 stars2 months ago
Inga-Lill is a friendly, gracious, responsive host. The apartment is well-positioned on the top floor of a high-rise building; truly wonderful views of Gulf, Tigertail Beach, natural preserve. The pool was a nice bonus and the complex and building were generally very quiet. Inga-Lill even provided a closet full of games, puzzles, everything needed for the beach, including a cart. We would definitely recommend!
Top guest favourite

Home in Marco Island
5 out of 5 average rating, 36 reviewsTropical Bahama Vacation Home
SoniaRating, 5 stars1 week ago
Our family had a wonderful stay at this Airbnb! The pool was the star of the trip — our kids absolutely loved it and spent hours swimming and playing. It was super clean, a perfect size, and safely maintained, which gave us peace of mind as parents. There were plenty of loungers and shade nearby, so we could relax while keeping an eye on the little ones. The whole backyard felt like a private oasis, perfect for family time and making great memories together. The home itself was cozy, spacious, and had everything we needed for a comfortable stay. We’d definitely return and recommend it to any families looking for a fun and relaxing getaway!
Destinations to explore
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Florida Keys Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Central Florida Holiday rentals
- Tampa Holiday rentals
- Seminole Holiday rentals
- Kissimmee Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Everglades National Park
- Tigertail Beach
- Clam Pass Park
- Panther Run Golf Club
- The Club at The Strand
- Talis Park Golf Club
- Worthington Country Club
- Esplanade Golf & Country Club of Naples
- Bonita National Golf & Country Club
- Seagate Beach Club
- Moorings Beach Private Park
- Stonebridge Country Club
- Residents' Beach
- Delnor-Wiggins Pass State Park
- Naples Botanical Gardens
- Barefoot beach Bonita Springs,FL
- Mediterra Golf Course
- Cypress Woods Golf & Country Club
- The Quarry Golf Club Naples
- Golf Club of the Everglades
- Bonita Bay Club Naples
- Quail Creek Country Club
- Valencia Golf & Country Club
- Shadow Wood Country Club