Holiday rentals in Chokoloskee Island

4.94 out of 5 average rating, 123 reviews

LUXE Oasis | 10 min Beach+5th Ave | HTD Pool• Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 🍽️ Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

Apartment in Marco Island

4.99 out of 5 average rating, 123 reviews

Waterfront View, Boat Dock, Pool Wildlife &Fishing

Unique Waterfront Condo & Gorgeous Intercoastal Views, Wildlife, Fishing, Boat Dock. One block from Snook Inn! Adjacent Pool Steps Away from Back Patio. NEWLY REMODELED! Pool & Patio Overlook Beautiful Waterfront, Dolphins, Manatees, Exotic Birds. Main Floor with no steps. If you love water and WILDLIFE, this place is for you! Fishing on the dock-Fishing Poles and Tack Supplied, pull your boat right to the back door. TONS of wildlife. Dock is lit at night, watch the sea life! NON SMOKING UNIT

Cottage in Everglades City

4.98 out of 5 average rating, 158 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

Superhost

Apartment in Everglades City

4.8 out of 5 average rating, 186 reviews

Everglade Isle Palms Condotel w/ Pool & Boat Ramp

It’s island time! Welcome to your home base for exploring the Florida Everglades. With all the comforts of home, our Condotel will be your ideal vacation spot. Explore Everglades National Park, the 10,000 islands, airboat tours, and more! Bring your boat or rent one for saltwater, brackish, & freshwater fishing- all from this unique & pristine area. Located in the heart of town, you’ll be in walking distance of several restaurants, ice cream parlors, and the grocery store.

4.94 out of 5 average rating, 31 reviews

Home in Everglades

Lostman's Lodge -Everglades City, Sunset View,Pool

Escape to the serene beauty of Everglades City at Lostman's Lodge, a spacious and beautiful waterfront property. This retreat offers accommodation for up to 10 guests, making it perfect for families, groups of friends, or couples seeking a tranquil getaway. With a main house and a charming pool house, a screened-in pool and hot tub, a dock, and amazing views of the water, this home is a true slice of paradise. It is not just a vacation rental; it's an experience!

4.95 out of 5 average rating, 155 reviews

Apartment in Naples

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.

4.98 out of 5 average rating, 133 reviews

Home in Marco Island

Top-rated luxury pool home in prime location

🏠Newly renovated & professionally designed 👙Amazing pool and outdoor kitchen (including grill, pizza oven, fridge)! 🏖️4 mins to beach 🌊Beach chairs, umbrellas, beach wagon & bikes 🐶Low pet fee; we love our 4-legged guests! 🧻Household supplies and personal amenities included ✅Fully stocked chef’s kitchen 🛌🏽Super comfortable beds for ultimate comfort and sleep 💻 High speed internet with dedicated workspace 😊24/7 local & professional host support

4.96 out of 5 average rating, 107 reviews

Tropical paradise 5 minutes from the beach

Come on in and unwind in this peaceful and one-of-a-kind oasis just a short 5-minute drive from Wiggins Pass beach! Feeling adventurous? Hop on a bike and you'll be there in a little over 15 minutes. Located in North Naples, this charming house is fully stocked with everything you need to cook, discover, unwind, and rejuvenate, this space even boasts its own private backyard. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

5 out of 5 average rating, 79 reviews

Home in Chokoloskee

The Reel'em Inn, Chokoloskee Island Paradise

Take in the tropical feel of Chokoloskee Island in an impeccably maintained 3 bedroom/2 bath single family stilt home nestled in the canopy of Royal Poinciana trees and palms. This fisherman's paradise is a unique find in a small fishing village in the heart of the Everglades National Park. Captain Brock Wagner is available for full day private fishing charters. After a day of fishing or kayaking simply relax in a rocking chair on the 600 sqft screen porch.

5 out of 5 average rating, 48 reviews

Home in Chokoloskee

Chokoloskee/Everglades City

Enjoy this cozy stilted home on Chokoloskee Island, located in the Everglades. The double lot makes it easy to travel with your boat, trailer or RV. 2 boat ramps are located less than 5 minutes away. There is plenty to do such as exploring Everglades National Park, kayaking or fishing the Ten Thousand Islands, and enjoying the freshest seafood. 6 bikes are available to use. The entire property is fenced in making it great for pets.

4.91 out of 5 average rating, 148 reviews

Cabin in Everglades City

Everglades City waterfront cabin

Bring your boat to this waterfront community in the heart of the Everglades and the 10,000 Islands. Across from Everglades National Park. Great fishing and boating community.. cozy cabin Sleeps up to 4 guests. Large outdoor living space. Community heated pool. 20$ boat launch fee to be paid next door at Glades store. Loft space and utility room are off limits to guests.

4.92 out of 5 average rating, 222 reviews

" The Bohemian Heaven " w/ SPA, 2miles to downtown

Welcome to the unique Bohemian Paradise. Completely renovated spectacular bright space, high-end furniture, a fantastic huge outdoor area, firepit, outdoor dining table, and BBQ station. Minutes away from restaurants and convenient stores, as well as historical Naples Pier, Naples beach, and 5th Ave/Downtown. You don't want to miss this experience.

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Other great holiday rentals in Chokoloskee Island

4.99 out of 5 average rating, 77 reviews

Villa in Marco Island

BEACH 5 MIN WALK | HEATED POOL | OUTDOOR KITCHEN

KennethRating, 5 stars1 month ago

BEAUTIFUL HOME. GREAT LOCATION. EXCELLENT HOST. I HIGHLY RECOMMEND. GREAT PLACE TO VISIT AGAIN AND AGAIN.

Superhost

4.95 out of 5 average rating, 66 reviews

Custom Designed Heated Pool and Spa

DashaRating, 5 stars7 months ago

This was our second time staying here and it was great. Me and my family were a bit nervous about the house since it was post both hurricanes but Jennifer was great at responding and made us feel comfortable. The house was great and so was the pool.

Superhost

Cabin in Everglades City

4.84 out of 5 average rating, 56 reviews

cabin2A screen room view of your dock nice view

DonRating, 5 stars1 month ago

This place is perfect for anyone trailering their boat from out of town looking for an opportunity to fish the Everglades. The location is ideal with direct access to the bay. When we arrived, our host kept the porch light on so we were able to make out the cabin number. The grounds has enough space for you to park your skiff next to the cabin. The water pressure on the hose is plenty strong to wash off the bait after a full day of fishing and there’s an exterior outlet to recharge batteries. Although we didn’t have to clean any fish, the cabin has enough resources to do so if you wish. This will be my spot when I go back to fish the Everglades.

4.98 out of 5 average rating, 47 reviews

Entire house: Pool : Kids play area

AmandaRating, 5 stars4 days ago

It was very quiet and peaceful. Nice place to get away and relax.

5 out of 5 average rating, 37 reviews

Welcome to Little Paradise

LucaRating, 5 stars2 weeks ago

We stayed for 2 nights with family and friends, and the experience was absolutely amazing! 🌟 The place is super clean, exactly like the pictures, and has such a peaceful atmosphere. The pool was spotless and perfectly warm, with jets that made it feel like a relaxing massage just what we needed to unwind! The house was very well equipped, with plenty of supplies and extra items available for guests to use. We appreciated the many towels and beach towels provided everything was thoughtfully prepared. 🏖️ Whether you’re coming with family, friends, or just looking for a romantic getaway, this place is a perfect choice. We absolutely recommend it to everyone and would love to come back! 💛

4.93 out of 5 average rating, 27 reviews

Home in Marco Island

THE Sandcastle at Marco Island!

JohnRating, 5 stars3 weeks ago

We had a wonderful time staying in your beautiful house. The pool and hot tub were such a treat. I will certainly tell friends about it. Hope to come back and enjoy it again.

5 out of 5 average rating, 9 reviews

Home in Marco Island

Waterfront with resort style pool/hot tub/fire pit

JessicaRating, 5 stars1 month ago

Kristen‘s home was a beautiful and comfortable place to stay! We booked five days with our family at her house and had a wonderful time. Everything was extremely clean, comfortable, and exceeded our expectations. Everything you could possibly need was available in her home. The location was great, the view in the backyard was stunning, And all the amenities were exceptional. Kristen was also a wonderful host and very accommodating/flexible to our family with two young kids. I would absolutely stay in her home again.