Holiday Homes in Lee County

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Top-rated Holiday Homes in Lee County

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite

An airy kitchen and dining area showcases light wood flooring and a spacious island with bar seating. White cabinetry contrasts with a vibrant blue backsplash. A dining table with blue chairs is accented by natural light from large windows, creating a bright and open space.

Holiday home in Fort Myers Beach

5.0 out of 5 average rating, 25 reviews

Heated pool, canal, outdoor kitchen & walk 2 Beach

Relax with the whole family at this peaceful place to stay on Fort Myers Beach. Fully renovated with 3 BR & 2 full bath. New central AC/ Heating unit. Enjoy a day in the heated pool or on your private dock looking out to the bay. 10 minute walk to the beach, Publix or the mid-island restaurants at the marina behind Publix. 3 BR, 2 bath with one room being a twin trundle bed. Enjoy one of the most quiet areas on the island to take walks or morning bike rides. Fully renovated since Ian & Milton

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The porch features a cozy lounge area, including a curved seating arrangement with soft cushions and a single reclining chair. A modern electric fireplace is mounted on the wall, providing a focal point. Natural light creates a pleasant ambiance through the open space.

Holiday home in Bonita Springs

4.71 out of 5 average rating, 161 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

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Guest favourite

Holiday home in Cape Coral

4.9 out of 5 average rating, 20 reviews

Seas the Day:Heated Pool + Canal View Near Beaches

Enjoy Florida at our family-friendly Cape Coral retreat — with a private heated pool, peaceful canal views, and everything you need for a memory-filled vacation. Start your mornings with coffee/tea from our beverage bar while relaxing on the patio or enjoying the wildlife out by the canal. Spend your days swimming in the heated pool, fishing, riding bikes or watching movies on our large sectional. At the end of the day, relax in comfortable bedrooms designed with hotel-inspired bedding.

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Top Guest favourite

A single-story home displays a light-colored exterior with white shutters and a covered entryway. Lush green plants in purple pots line the front, providing a touch of color. A spacious driveway is visible, leading to the entrance, with a clear sky overhead.

Holiday home in St. James City

5.0 out of 5 average rating, 11 reviews

Pine Island Paradise- Saltwater Canal 2 Bed/2 Bath

Looking for your piece of island paradise? This beautifully decorated spacious 2 bedroom, 2 bathroom home in St. James City, sits on a salt water canal minutes away by boat from the Intercoastal Waterway, Sanibel, Captiva, Ft. Myers Beach, and some of the best fishing in all of SW Florida! The home comes with a 7,000# boat lift and fishing cleaning station on the dock where you can see Manatee and dolphins in the canal. It is also within minutes of 5 restaurants and 2 grocery stores!

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Top Guest favourite

A vibrant entrance to a colorful house is shown, featuring a blue pathway leading to a door framed by bright decorations. A serene aerial view displays the layout of Matlacha, highlighting its waterfront and artistic community.

Holiday home in Matlacha

4.95 out of 5 average rating, 21 reviews

Serenity Point~ Island Time Begins Here

Escape to Matlacha Bay, a place we call Serenity Point. where sunrise glows across the water and moonlit evenings invite you to unwind. Explore colorful galleries and shops, savor fresh seafood, kayak quiet waterways, or enjoy renowned fishing—then return to your peaceful bayfront retreat. Minutes from Cape Coral and Pine Island, this Old Florida gem feels worlds away. Hypoallergenic pets and dock use require advance approval. Book now and make your waterfront getaway unforgettable!

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Top Guest favourite

An aerial view captures a spacious two-story home nestled in a private, gated community by a serene waterfront. Lush palm trees and meticulously landscaped gardens flank the driveway, leading toward the entrance. The tranquil water reflects the surrounding greenery, enhancing the peaceful setting.

Holiday home in Iona

4.98 out of 5 average rating, 80 reviews

5 Bdrms! Waterview! 10 minutes to Fort Myers Beach

- Gorgeous water view - Heated Pool - NO charge to heat the pool! - Private, gated community - Less than 10 minutes from Fort Myers Beach!!! - Free WiFi - Extra large home with two stories - Open, light, bright and airy! **Dedicated Concierge included to help arrange every part of your stay including transportation, private chef, celebration decor, massages, fishing trips, yoga + more! We want YOU to stay with us on your trip! Tell us what we can do to host you :)

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Guest favourite

An aerial view displays the beachfront property surrounded by expansive green areas and well-maintained roads. The ocean sparkles in the distance, while tennis courts are visible nearby. Ample parking spaces are situated in the foreground, enhancing accessibility for guests.

Holiday home in North Naples

4.86 out of 5 average rating, 50 reviews

Naples/Bonita Beach Luxury Condo with two pools!

Note: Both pools have been renovated and are now open! No tennis/pickleball until further notice. Location is key!! 5 minute walk to the Barefoot and Bonita Beaches!! Relax at the beach or enjoy the beautiful Florida sunshine! This unit provides beach chairs and towels for the outstanding vacation spot. Jet-ski, keyaki, paddle boarding are available to rent on the beach. Two excellent restaurants within walking distance. Come see what Bonita Beach has to offer.

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Guest favourite

A bright and airy living space features an open layout connecting the kitchen and dining area. Contemporary furniture includes patterned chairs and a soft grey sofa. A round table sits at the center, while a decorative mirror hangs on the wall, reflecting natural light throughout the room.

Holiday home in Bonita Springs

4.92 out of 5 average rating, 36 reviews

Modern Home w/ Hot Tub Near Beaches/ Coconut Point

Unwind in this modern escape, perfect for up to 6 guests. The home features a hot tub, king-size bed, a convertible twin beds to a King size if desired, queen-size pull-out sofa. Enjoying BBQ on the screened large patio. With a 1-car garage and a LARGE driveway, plenty of room boat or RV. Located just 0.5 miles to Hyatt Regency Resort, 8 miles to beaches, 1 mile to Coconut Point Mall, 6 miles to Gulf Coast Center, 10 miles to Mercato, and 8 miles to RSW Airport.

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Superhost

A charming two-story home is nestled among lush greenery and large trees, featuring a welcoming porch with white railings. Flowerbeds line the walkway leading to the front door, while a gravel driveway extends to the side. The surrounding area showcases colorful houses.

Holiday home in Fort Myers

4.94 out of 5 average rating, 148 reviews

Cozy Boho Escape! Walkable to Downtown attractions

Relax and enjoy all downtown Fort Myers has to offer! This historic home on a former guava plantation is a 7 minute walk to the historic River District - chock-full of shops, theaters and nightlife. Enjoy one of the many delicious restaurants within walking distance, or prepare a meal in the Casita's well-stocked kitchen and enjoy eating under the pergola in the backyard. There's no better place to enjoy the old Florida charm of Gardner's Park.

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Guest favourite

A screened lanai frames a sparkling pool, reflecting the blue sky and water beyond. Lush greenery lines the pool area, enhancing the view of the calm river. The boat lift is visible, ready for water activities.

Holiday home in Matlacha

4.9 out of 5 average rating, 21 reviews

Nature Lover's Dream - Waterfront Living Matlacha

Matlacha is a taste of Old Florida where the living is carefree, the views are amazing, the seafood is fresh-caught. This Gulf access home is centrally located to all SW Florida offers. Perfect for those who like to try something different each day or just want to chill in an island oasis among the dolphins, mantees & seabirds. Nestled in the heart of Matlacha, you will love the views & sunsets. 2 King Bedrooms, one queen and 1 pull-out sofa.

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A scenic view is presented from the balcony, showcasing a vibrant sunset over the water. The horizon is painted in shades of orange and purple, reflecting off the calm surface. The railing of the balcony is visible in the foreground, framing the serene landscape.

Holiday home in Punta Rassa

4.85 out of 5 average rating, 101 reviews

Sanibel Harbour Tower Highest Views #1112

SANIBEL HARBOUR TOWER CONDO-11TH FLOOR. 2 towers is 1 of the top-shelf condo communities in the area. Upscale living 11 floor Rare! ENJOY OUR SANDY BEACH PRIVATE Panoramic 180 view OF DOLPHINS, MANATEES & BOATERS GO BY YOUR WATERS EDGE VIEW. KING-MASTER, QUEEN-SPARE & SLEEPER SOFA LAUNDRY IN MASTER BATH. WE ARE LOCATED JUST PAST THE SANIBEL MARRIOT RESORT (WE ARE AT THE CLU DE SAC, END OF ROAD.....QUITE!!)

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Guest favourite

The image captures a serene sunset over water, with vibrant rays of orange and blue illuminating the sky. Silhouettes of palm trees frame the scene, while the tranquil surface of the water reflects the colorful hues of the sky.

Holiday home in Matlacha

4.8 out of 5 average rating, 10 reviews

Turtle House - Waterfront w/ Dock

Peaceful yet centrally located, this beautifully decorated waterfront home offers incredible views and effortless access to the waterways. Enjoy breathtaking sunsets while relaxing by the water, or stroll to Matlacha’s shops, galleries, and restaurants. Recently remodeled and professionally designed, the home provides all the comforts needed for the perfect getaway or extended stay.

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