Holiday rentals in Chokoloskee

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Top-rated holiday rentals in Chokoloskee

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

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Superhost

Apartment in Fort Myers Beach

4.92 out of 5 average rating, 196 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

BEACHES ARE OPEN! Beautiful Views, large unit, Enjoy the sun, beach, and excitement of Florida. Lovers Key State Park, beautiful beaches, hiking & biking trails, Ft Myers Beach, white sand, many activities. Views of the gulf & bay area. Exercise room, wifi, great swimming pool- the beaches & trails you come to Florida for. Ft Myers beach has the white sand you think of when visiting Florida. The Gulf Coast Beach, and Lovers Key State Park are there for your enjoyment. Great place for Memories

Guest favourite

Home in Naples Park

4.95 out of 5 average rating, 22 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)

Guest favourite

Apartment in Sanibel

4.95 out of 5 average rating, 80 reviews

Right on the Beach with the Best Views and Rates!

Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Amazing views of the Gulf with 5 star ratings! 3-day min. Sustained min. damage from Hurricane Ian. New hurricane windows, freshly painted with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1: King bed, en suite, smart TV. BR 2: 2 twin beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow small dog.

Top guest favourite

Flat in Fort Myers Beach

4.99 out of 5 average rating, 70 reviews

Island Sunshine Poolside Gem

Important Note: This apartment has been totally remodeled from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Perfectly remodeled bright and cheery poolside apartment. This one truly has it all. From luxury bedding to a fully equipped kitchen to a spacious screen porch right outside the living room door. This dreamy island apartment offers a king me

Top guest favourite

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

Apartment in Bonita Springs

4.93 out of 5 average rating, 67 reviews

Bonita Springs/Gulf View 9th Floor/steps to Beach!

Gulf Views of Bonita Beach Coastline from your 9th Floor Lanai! -One from the Penthouse -Beautiful Beaches -Sunset Just Across the Street!!- On the beach Every Night- Everything included for an Amazing Stay- including -Beach chairs ,Umbrella- Free WIFI -Just bring Shampoo and get ready to have some Fun!! A famous bar and grill right on the Beach with your favorite Cocktails and Happy Hour all day long- OUR PRICES ARE DISCOUNTED off season and for longer stays -just send in a request!!

Guest favourite

Home in Marco Island

4.93 out of 5 average rating, 29 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

Guest favourite

Home in Bonita Springs

4.83 out of 5 average rating, 18 reviews

Stunning Lakefront 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!

Guest favourite

Home in Naples Park

4.96 out of 5 average rating, 70 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!

Top guest favourite

Apartment in East Naples

5 out of 5 average rating, 6 reviews

Naples Tyme Retreat

New spring rates! Enjoy Spring at Naples Tyme Retreat — an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, tennis, and world-class dining. Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.

Top guest favourite

Home in Marco Island

4.98 out of 5 average rating, 302 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

Cottage in Fort Myers Beach

4.89 out of 5 average rating, 28 reviews

DEJA BLUE 1000 FT from Beach Great for Families

1000 ft from the beach No car needed!!!! Walk around town or Trolley Best location on beach Perfect vacation spot, beautiful sunsets Newly renovated Close to time square restaurants and shopping. Relax on landscaped palm tree front patio 3 New flat screen tv’s and Brand new stainless kitchen Beach chairs, umbrella and towels are ready to go to the beach Backyard with grill Let’s book and start your vacation!!!!!!!!!!!!!!!!!!!!!!