Holiday houses in Chokoloskee Island

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Top-rated holiday rentals in Chokoloskee Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Naples

5.0 out of 5 average rating, 133 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

21 – 28 June

$1,657 AUD total

Superhost

Holiday home in Bonita Springs

4.8 out of 5 average rating, 106 reviews

Amazing home w canal views, a mile from the beach!

New&Amazing location Walk or bike riding distance from the best escape to the most beautiful beach locations in Southwest Florida . This 1-bedroom, 2-bed and fold up bed spacious home has an open floor to allow the family to enjoy time away from home. The porch has seating to watch the sunsets with canal views. Step outside to relax play board games or just enjoy the fireplace while you chat with the family. This great place with lots of room for fun. Short distance to Fort Myers, Naples.Miami2

20 – 27 Aug

$1,489 AUD total

Guest favourite

Guest suite in Naples

4.98 out of 5 average rating, 337 reviews

Naples Loft

Beautiful new construction loft that offers 640 square feet of open floor plan! This unit sits above our two car garage , 130 feet from the main house. Full kitchen, microwave, coffeemaker, toaster, iron, and washer/dryer! Our home sits on 1.14 acres with a circular driveway in a very quiet neighborhood. Enjoy organic farm fresh eggs from our backyard chickens! If you have children, your welcome to play in the "island" (our kids play area) with a playhouse and climbing dome. Very relaxing place!

7 – 14 June

$1,345 AUD total

Superhost

Guesthouse in Naples

4.8 out of 5 average rating, 296 reviews

Waterfront Sea Cottage

*Newly rebuilt after Hurricane Ian. Expect some construction within the main home. Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

23 – 30 Sept

$1,212 AUD total

Guest favourite

Cottage in Ochopee

4.99 out of 5 average rating, 109 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.

30 Aug – 6 Sept

$4,655 AUD total

Guest favourite

Guest suite in Naples

4.97 out of 5 average rating, 303 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

14 – 21 Nov

$1,521 AUD total

Guest favourite

Apartment in Marco Island

4.93 out of 5 average rating, 224 reviews

Best JW Marriott Alternative Prime~ Location~Pool

Retreat to the gorgeous 1BR 1Bath coastal oasis located across the street from JP Marriot, offering easy access to the exciting attractions and beaches of Marco Island. The condo's design, comforts, amenities, and central location provide everything you need to relax, recharge, entertain, and have a perfect Gulf Coast stay! ✔ Comfortable King Bedroom ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Community Amenities (Pool, Hot Tub, Parking) Learn more below!

23 – 30 Sept

$2,822 AUD total

Guest favourite

Tiny home in Naples

5.0 out of 5 average rating, 143 reviews

BEACHYVibes TINY House Pickleball Ct Mile to Beach

From the minute you step inside our “Tiny House" the beachy vibe gently reminds you of why you came! The 12' living room makes the 400 sq ft space feel more expansive. Sailor’s knot rope tied around anchored cleats create a banister/railing to the 6’2” spacious loft bedroom. Nestled below an eat-in kitchen and full bath. Located less than one mile from the beach in the center of the city hustle, the stand alone new construction has a private entrance and luscious outdoor private patio.

14 – 21 Aug

$1,922 AUD total

Guest favourite

Apartment in Naples

4.98 out of 5 average rating, 168 reviews

Bear Necessities - 1 Bdrm 1 Bthrm w/Kitchen/Lvrm

Relax and enjoy Florida indoors and outdoors in this "mini-apartment". You can watch for roaming wildlife and enjoy the tall pine trees, palm trees, and cypress trees from the patio. The "mini-apartment" is within walking distance of the canal where you can go bird watching and possibly see other wildlife. The apartment is outside of the busy hustle and bustle of the city but within driving distance of the beach. There are several restaurants with indoor or outdoor dining options.

16 – 23 Mar

$1,352 AUD total

Guest favourite

Guesthouse in Naples

4.93 out of 5 average rating, 113 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

23 – 30 Aug

$1,830 AUD total

Guest favourite

Cabin in Bonita Springs

4.91 out of 5 average rating, 277 reviews

Calming, relaxing cabin on the Imperial River

This private cabin surrounded by beautiful Florida landscape is the perfect place to get away from the stress and pressures of life. Unique decor from local artists, water filtration cooler, View birds, otters, manatees, turtles and fish in the river right outside your door. At night, sit on the screen porch under the soothing cafe lights protected from rain and bugs. Pagoda offers seating for 4, gas grill and chaise lounge for dining and relaxing. Come unwind in this gem!

25 June – 2 July

$1,360 AUD total

Guest favourite

Home in Naples

4.97 out of 5 average rating, 110 reviews

Everglades Nature House.

Attention Nature Lovers! The house is on 3 acres of Florida Everglades landscape. You will enjoy the sound of the wind through the pine, oak and palm trees surrounding the property. You may be to able see wildlife such as hawks, owls, kites, turkey, deer, bears, bobcats, or panthers. A canal is a short walk down the street, you may see alligators and wading birds. The property is very relaxing, a great place to get away and gaze at the stars and hear owls hoot.

29 Oct – 5 Nov

$1,542 AUD total