Holiday houses in Chokoloskee Island

4.94 out of 5 average rating, 125 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!

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.

4.95 out of 5 average rating, 156 reviews

Condo 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. We do not offer snorkeling gear.

5 out of 5 average rating, 38 reviews

Home in Ochopee

The Everglades House

We welcome you to your next adventure! This 3-bedroom home is located in a unique, historic "Old-Florida" style town known as Everglades City (a.k.a. Ochopee). Home includes beautiful & serene waterfront views where you can lie back, relax, read a book or have a drink, while your kids can fish from the dock! You can enjoy activities like airboat tours, eco/wildlife-tours, fishing guides, bicycling, kayaking, walk the nature trails local bars and restaurants. We look forward to hosting you!

Superhost

Condo in Everglades City

4.8 out of 5 average rating, 187 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!

4.96 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.

4.95 out of 5 average rating, 304 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

We welcome you to our high end, next level, brand new Farmhouse, which is conveniently located in the heart of Naples. Only 1.5 miles away from the beach, minutes away from the nearby plaza, which offers dining experience, shops, supermarkets, gas stations, etc. The well-known downtown district is only four miles away and Mercato, if you are looking for nighttime activities. Brand new High-end furniture and beds. Welcome, Home!

4.91 out of 5 average rating, 149 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.

4.93 out of 5 average rating, 227 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chokoloskee Island holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chokoloskee Island

5 out of 5 average rating, 10 reviews

Beachfront unit w/amazing views

ValeriyaRating, 5 stars1 month ago

We enjoyed our recent stay at this condo - the views were beautiful, you can watch the sun set from the master bed! Some highlights were beach proximity (building is on the beach you just have to cross the sand for 10 min to get to the water), great responsive host, good value, proximity to restaurants & grocery stores, and cleanliness. There were beach chairs, wagon, big beach blanket, and toys for little ones in the unit which was very convenient. The bed in the main room was comfortable and bathrooms had all the essentials. The unit could use some cosmetic updates, but that did not impact the overall enjoyment of our stay. Overall, a great option for a Marco Island vacation.

Superhost

Home in Fort Myers Beach

5 out of 5 average rating, 3 reviews

NEW 3 BD • POOL • 3 min walk to BEACH!

KellyRating, 5 stars3 days ago

Had such a great stay. The house was super comfortable and had all the touches of home—from cozy surroundings to thoughtful amenities, even in the bathrooms, which really made it nice. My (grown) kids ❤️ and I had the best time—short walk to the beach, ( full beach gear available) and the pool was perfect to come back to and unwind. The owners were super responsive to any requests we had, which made the whole experience even better. We packed in a lot of fun and laughs, and this place made it all easy and relaxing. Would definitely stay here again!

4.95 out of 5 average rating, 39 reviews

819 Tropical Bliss · Heated Pool/Spa · Walk2Beach

CarlosRating, 5 stars1 week ago

Phenomenal stay. The place was spotless and fully stocked with everything you need for cooking and comfort. The guidebook was super helpful, and the hosts made sure we knew all the best spots in the area. Highly recommend—everything was seamless from start to finish.

Superhost

4.89 out of 5 average rating, 44 reviews

Apollo 9th floor beautiful beachfront

LeslieRating, 5 stars1 month ago

Wonderful stay, great location, beautiful beach. The Marco Island community is friendly and inviting, they always make you feel welcome.

4.94 out of 5 average rating, 32 reviews

Oceanfront Condo in Apollo, Marco Island

Doris ARating, 5 starstoday

We've rented other condos for years all over the country, but this one has been the best experience. The host answered every question I had in a timely manner. They provided little extras that you might need if you've flown in. Shampoo, soap, coffee, etc. I liked that we could go downstairs to the restaurant next door for a drink, then a sit on the beach. The location was good too. Not a lot of traffic down that way, so that was nice. Many restaurants and grills in a 5 mile radius. The condo is nicely decorated. Bed was comfy. Furniture was comfy. If we ever get the chance, we'll be going back. I highly recommend it.

4.95 out of 5 average rating, 61 reviews

Home in Marco Island

Relaxation on the water Monthly discounts! Inquire

ChadRating, 5 stars3 months ago

Nice place, responsive owner, could not have asked for anything more! So many towels, beach chairs, bikes, top notch amenities. Nice quiet neighborhood - look for the cute owls!

5 out of 5 average rating, 8 reviews

Beach, Sun & Walk to Everything ~Instaworthy Vacay

VandaRating, 5 stars10 months ago

Second time I’ve visited this property — location/comfort are exceptional, Marco beaches are my favorite, and home had everything I could ask for in a large and comfortable space. Highly recommend for a relaxing beach vacation!