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Holiday houses in Estero Island

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Top-rated holiday rentals in Estero Island

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

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Holiday home in Bonita Springs

4.79 out of 5 average rating, 107 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

$210 NZD per night

Home in Fort Myers

4.85 out of 5 average rating, 596 reviews

Tiny house 5 miles from Sanibel / free amenities

Tiny Paddle Board House Stay on adventure's doorstep! 5 miles to FMB and Sanibel island (beaches, salt water fishing, paddle boarding, kayaking ). Are guests enjoy free amenities: 1. Breakfast items (eggs, bagels, apples, coffee and tea) 2. Bicycles 3. SUP - inflatable paddle board 4. BBQ gas grill 5. Beach chairs and umbrella 6. Cooler and beach towels 7. Secured Wi-Fi 8. Amazon TV, Netflix, Hulu, Disney +, ESPN+ 9. Parking 2 cars 10. Washer and dryer in house 11. Kids toys and books

19–26 Oct

$226 NZD per night

Guest favourite

Cottage in Saint James City

5.0 out of 5 average rating, 27 reviews

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Just under 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

23–30 Jul

$300 NZD per night

Guest favourite

Guesthouse in Fort Myers

5.0 out of 5 average rating, 35 reviews

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal with a one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Bring your boat and dock it on the seawall, ready to set sail whenever your heart desires. (PLEASE NOTE-boats only) Book now - your coastal paradise awaits!

23–30 Nov

$297 NZD per night

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.

29 Aug – 5 Sep

$235 NZD per night

Guest favourite

Home in Fort Myers

4.8 out of 5 average rating, 265 reviews

Amazon Bungalow near Sanibel & Fort Myers Beach

Tropical setting. Peaceful/quite neighborhood. Bunche Beach 2 miles, Sanibel Island 3.5 miles, Fort Myers Bch 5 miles. Home is set up as a duplex, with TWO COMPLETELY SEPERATE & PRIVATE entrances, kitchens, living rooms, bedrooms, bathrooms & laundry rooms for COMPLETE PRIVACY. The Bungalow is a 1 King bed, 1 full bathroom & shower with large living room, kitchen & porch. Perfect for Couples! • 1/2 mile to Restaurants and Shopping • Close to Shellpoint Golf-Course • FREE Wi-Fi and Cable-TV

29 Oct – 5 Nov

$253 NZD per night

Guest favourite

Guesthouse in Fort Myers Beach

4.93 out of 5 average rating, 14 reviews

Lil Lavender

You will be close to the action when you stay in our 330 sq ft fully renovated studio suite with queen bed, seating area, dining table and walk-in shower. 1.5 block walk to the beach and <1 mile to Times Square and Margaritaville. Mini kitchenette inside and gas grill outside. Kitchen supplies, toiletries, wagon, cooler, umbrella, beach towels and chairs provided. NOTE: Suite has 2 private entrances but shares a wall with the owner-occupied main portion of home. No 3rd-party bookings.

10–17 Sep

$340 NZD per night

Guest favourite

Guest suite in Fort Myers

4.97 out of 5 average rating, 230 reviews

Clean studio unit with bathroom and living room

Enjoy a cozy stay in our studio. We're centrally-located in the heart of Fort Myers, with the interstate, RSW airport and Gulf Coast Town Center shops right around the corner. The beach is only a 25 minute drive, 10 minutes to the outlets, and 25 minutes to downtown. It's nice and quiet inside, with a place to work, relax to some TV, and has a comfortable queen size bed and a futon for an extra person. We have a full bathroom, mini-fridge, microwave, towels and plates to enjoy a meal.

12–19 Mar

$194 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.97 out of 5 average rating, 68 reviews

Scenic Retreat with Private Balcony

A studio apartment more than just a room. Less than a mile from Time’s Square, the beach center, and the remains of the pier. Beach access is a 5 minute walk. Close to public transportation and located on a quiet street with a private backyard on a canal. If you’re lucky, catch a glimpse of a dolphin or manatee. Private entrance and deck. Newly remodeled kitchenette and laundry room. If this sounds like what you’ve been looking for, instant book now or text me with any questions.

2–9 Dec

$293 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.98 out of 5 average rating, 41 reviews

Island Sunshine Poolside Gem

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 memory foam mattress in the master bedroom and a queen sleeper sofa in the living room. On top of it all the location is on a quiet street one block to the gorgeous powered sugar sandy beach. All this is sure to make any vacation unforgettable.

8–15 Jun

$347 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 146 reviews

Casa Bella B - 1 Bed/1 Bath - Steps To The Beach

Fort Myers Beach Short Term Rental #21-0112. Fresh, clean and cozy, this 1 bedroom, 1 bath condo is located directly across the street from the Gulf Of Mexico and 7 miles of sugar sand beach. Public beach access is a 3-minute walk south on Dakota Ave. Located mid-island Casa Bella B is close to all amenities including a grocery store and restaurants. The popular Island Trolly services the length of the island from Times Square to Lover's Key State Park.

7–14 Aug

$378 NZD per night

Guest favourite

Home in Fort Myers

4.92 out of 5 average rating, 203 reviews

*Unique Pyramid Home for an amazing vacation

*Great location for exploring all of southwest Florida *Refreshing spring water lake for all guests to enjoy *located approximately 15 miles from most beaches *easy access to FGCU, shopping, sightseeing, RSW airport *self check in with lock box *Private and relaxing community *each pyramid has two private patios with private gas grill *free wifi/ roku tv, beach gear * superhost with 12 total properties *Fully stocked unit with all the amenities of home

12–19 Oct

$320 NZD per night

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Popular amenities for Estero Island holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Estero Island

Guest favourite

Tiny home in Fort Myers

5.0 out of 5 average rating, 48 reviews

Tiny Home close to beach- Sun Kissed Hide-A-Way

10–17 Jul

$244 NZD per night

Guest favourite

Home in Fort Myers Beach

5.0 out of 5 average rating, 40 reviews

Luxury Coastal Farmhouse just steps from beach!

25 Sep – 2 Oct

$678 NZD per night

Guest favourite

Home in Fort Myers Beach

5.0 out of 5 average rating, 5 reviews

Happy Horizons

6–13 Jun

$1,131 NZD per night

Guest favourite

Home in Fort Myers Beach

5.0 out of 5 average rating, 67 reviews

Paradise on canal minutes to Ft Myers Beach/Gulf

2–9 Mar

$1,718 NZD per night

Guest favourite

Home in Fort Myers

4.94 out of 5 average rating, 32 reviews

So Coastal! A family and pet friendly home

30 Nov – 7 Dec

$299 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.96 out of 5 average rating, 23 reviews

Walking distance to Time Square area - Sunset view

13–20 Jul

$301 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.99 out of 5 average rating, 84 reviews

Ready to Enjoy again! Everything is brand new!

26 Jan – 2 Feb

$689 NZD per night

Guest favourite

Apartment in Naples

5.0 out of 5 average rating, 37 reviews

Las Casitas in Naples

20–27 Sep

$229 NZD per night

Destinations to explore