Holiday houses in Chokoloskee Island

4.98 out of 5 average rating, 133 reviews

POOL HOUSE, CLOSE TO THE BEACH & DOWN TOWN NAPLES!

HEATED Pool home - Completely renovated home that comfortably sleeps 6 Only 5 minutes to the most desirable Beaches in the USA! Also very close to incredible restaurants, Publix, Target, Shopping, Parks and only 10 minutes to Downtown Naples. Flat-Screen TVs, Hi-Speed Internet, Comfy beds, modern and fully-stocked Kitchen. Very private and large pool with outside grill and patio furniture. Perfect for relaxing after a long day at the beach, we look forward to welcoming you to our HAPPY PLACE!

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.

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!

4.98 out of 5 average rating, 88 reviews

Flamingo Paradise 4 min walk from Beach Access.

Time, and worries of the rest of the world, will melt away as you are captured by the serenity of this beautiful location. This 3 bedroom home accommodates up to 8 guest, all with its own private heated pool. This is the best option to create the story of a perfect vacation with family and friends. This house is newly renovated with a modern look steps away from the beautiful white sanded beach. Its fully equipped with gym, laundry, BBQ, and even with bikes for the whole family.

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!

4.98 out of 5 average rating, 134 reviews

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.

5 out of 5 average rating, 64 reviews

Luxe King EnSuites ·Heated Saltwater Pool/Spa

Welcome to 716 Coastal Dreams! This stunning coastal vacation home, a luxurious, new build 5-bedroom w/ 3 kings and 1 double queen ensuite that combines the timeless allure of the seaside with modern elegance. Nestled in a serene coastal enclave, this property offers the perfect escape for those seeking relaxation, comfort, and the allure of the ocean. · · · Book NOW before this Beautiful Home becomes a well known Treasure! · · ·

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Other great holiday rentals in Chokoloskee Island

5 out of 5 average rating, 10 reviews

Condo in Marco Island

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.

5 out of 5 average rating, 17 reviews

Total Haven on Marco Island

MarciRating, 5 stars3 weeks ago

Hopes place was beautiful. It is brand new and in a great location. Every amenity was there and it felt like home. The only issue I had was the smoke detector battery died at 2am and that noise is loud and doesn’t stop until you fix it. Hope had it fixed the next morning. The other issue odd we rented paddle boards for the weekend thinking we could use the dock to lower them in be water but it was broke and wouldn’t be fixed at all to use. We had already paid so lost money on that. I would definitely stay here again even with the few issues we had. Hope was very responsive and we loved being on the water. Went fishing right off the dock and caught fish. Amazing place with a few hiccups.

4.94 out of 5 average rating, 17 reviews

Condo in Sanibel

"Seaspray" - beachfront, Amazing GULF VIEWS!

AndrewRating, 5 stars1 week ago

Katlyn was a great host and the condo was perfect for our family vacation. We love Sanibel and the location near the lighthouse is the best you can ask for on the island. The unit was well equipped for our family and the extra beach chairs and umbrella were much appreciated. We’ll definitely be back to Sanibel for years to come and will look to book here again.

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.

4.96 out of 5 average rating, 27 reviews

Marco Island Waterfront Home w/Heated Pool + Bikes

RebeccaRating, 5 stars2 months ago

We had the most wonderful time in this home. We think it was one of the most beautiful Airbnb's we have rented. My husband and I traveled with 5 teenage boys. The home was perfect. The layout was outstanding and each room was just what was needed. The location can't be beat and Koury supplied bikes which was a massive perk. The boys were able to easily bike to the beach, shops, restaurants, and then relax in the pool after a long day. Koury was responsive both before and during our stay when I had a few questions. We honestly can't say enough! We would definitely return if we decide to go back to Marco Island!!

Villa in Everglades City

5 out of 5 average rating, 3 reviews

Villa Serena - Tranquility Redefined

LaurenRating, 5 stars3 weeks ago

This house is absolutely beautiful, on a great spot on the canal. Set up perfectly for bringing your boat with outlets at the docks for charging, hoses for spraying down the boat. The house is pristine and of our 3 trips to Everglades city, is by far the nicest place we’ve stayed. Joanna was super proactive and helpful providing information about boat ramps etc. Thanks so much!

5 out of 5 average rating, 5 reviews

Coastal 4BR Retreat - Vanderbilt Beach Pool & Dock

Graham LloydRating, 5 stars7 months ago

We holiday twice a year in and around the waterways. This property is without doubt the best we have stayed in. The location, the furniture, everything in the house was excellent. Crissy was always on hand and on a couple of occasions had some items delivered immediately to the house…. Such a superb host and a pleasure to deal with. Nothing was a problem at all for her…. Thank you for a wonderful holiday!