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.

Superhost

Home in Naples

4.94 out of 5 average rating, 17 reviews

Poolside Paradise

Relax with the whole family at this peaceful place to stay. While new to Airbnb, this vacation gem has been the #1 home in Naples Park for years on VRBO. With over 300 5-star reviews our home boasts a private heated pool, less than one mile from the beach, rocking chairs to sip morning coffee on the front porch as well as only a few miles from 10+ Naples golf courses. We provide all the beach towels, soap, shampoo, laundry soap, weber grill, 4 bicycles, portable baby crib, and baby chair. :0)

Superhost

Home in Bonita Springs

5 out of 5 average rating, 17 reviews

Casa Bonita by the Sea

Indulge in a dream vacation at our 3-bedroom oasis near one of Florida's top beaches. Inside this brand new home, bask in natural light and chic decor. Unwind on the reclining sofa, step outside to your private paradise with a saltwater pool, infinity spa, and outdoor kitchen. The master suite offers luxury with pool access, soaker tub and shower. Enjoy nearby beach activities, hiking, shopping and dining. Every detail is designed for your relaxation. Book now for the ultimate coastal retreat!

Superhost

Home in Naples

4.95 out of 5 average rating, 59 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

Superhost

Home in Marco Island

4.92 out of 5 average rating, 24 reviews

STUNNING Canal Ranch Walk to the Tigertail Beach

NEW LISTING! Newly Remodeled 4 Bed, 2 Bath that sits in a very exclusive location less than 2 blocks from Tigertail Beach! Our vacation home offers an abundance of updated space! Plenty of outdoor entertaining within the large enclosed pool area. Enjoy the several "extras" to use during your stay including, bikes, beach chairs, coolers, and much more! You won't find a better value for your family and be able to walk to the beach! Please note: TV in every room set up for streaming ONLY

Superhost

Apartment in Bonita Springs

4.82 out of 5 average rating, 28 reviews

Stay In The Penthouse--Spectacular Views & Sunsets

Our proximity to one of the best beaches in the world on the Gulf of Mexico as well as our flexible rental program is unique in Southwest Florida. We are dedicated to insuring you have a relaxing, enjoyable and unforgettable stay with us and that you will return year after year!!! We are located on the beautiful six-mile Bonita Beach in Florida. We are close to Southwest Florida International Airport (RSW). Ours is a friendly and welcoming community of owners and their Guests.

Superhost

Home in Bonita Springs

4.75 out of 5 average rating, 12 reviews

Stunning Lakefront Solar Heated Pool & Spa House!

Your perfect getaway awaits! Escape to tranquility in our beautifully updated 3/2 lakefront retreat with a heated (optional for a fee) pool and spa! This remodeled peaceful gem is nestled on a serene, private lot with breathtaking lake views. Just 7 miles to the pristine Bonita Beach and minutes from, shopping, and dining. Don’t miss out on this extraordinary retreat where comfort meets nature. Book your stay today and experience the ultimate in relaxation and luxury!

Superhost

Home in Naples

4.95 out of 5 average rating, 61 reviews

Blue Tides Inn

Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation with a tropical pool. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

Superhost

Home in Marco Island

4.98 out of 5 average rating, 298 reviews

⭐ Rare Waterfront Western Exposure Vacation Home

This dream getaway home is located in the heart of Marco Island with everything you need for an unforgettable trip! Enjoy the convenience of being only minutes away from South Marco Beach, with its white sand and clear blue skies, and the best restaurants such as Da Vinci's, Marco Prime, The Snook Inn, The Oyster Bar and shopping on the Island! Wind down your day watching breathtaking Western exposure sunsets from your own waterfront patio and dock...

Superhost

Home in Naples

4.93 out of 5 average rating, 134 reviews

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Superhost

Apartment in Marco Island

4.6 out of 5 average rating, 5 reviews

Angler Oasis III-Marco Waterfront Condo - 5 Star!

LOCATION! LOCATION! We are Superhosts This tropical escape has a laid back style all it's own. A 1 BDR condo that sleeps 4 is located right on the water with water views, 2 pools, tennis courts and the Dolphin Tiki Bar are all on the grounds. Fish right off the dock or rent a boat at Rose's Marina which is right next door. There are so many reasons you'll love your stay. LOCATION! LOCATION!

Superhost

Apartment in Bonita Springs

4.92 out of 5 average rating, 66 reviews

Bonita Springs-Paradise w/Gulf View steps to Beach

Gulf Views of Bonita Beach Coastline from your lanai! One of the most Beautiful Beaches just across the street-with White Sandy beaches and Sunsets On the beach- Everything included for a Comfy stay-Beach chairs - Umbrella- Free WIFI -Just bring Shampoo!! ---PRICES DISCOUNTED while Pools and Buildings are Upgraded! until January

Superhost

Home in Naples

5 out of 5 average rating, 99 reviews

Cozy Vacation Home * Heated Pool*Near The Beach !

You can stop looking for the perfect vacation home in an amazing location! This home is comfortable, artsy, inviting and full of charisma! Enjoy the fun decorations, resort style outdoor entertainment area with outdoor seating, BBQ and a relaxing gazebo. Located just a 3 minute to the nearest beach on a quiet neighborhood.