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Waterfront holiday rentals in Estero Island

Find and book unique waterfront accommodation on Airbnb

Top-rated waterfront accommodation in Estero Island

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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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 Apr

$253 NZD per night

Guest favourite

Cottage in Matlacha

4.88 out of 5 average rating, 134 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

23–30 Nov

$255 NZD per night

Condo in Fort Myers Beach

4.95 out of 5 average rating, 65 reviews

Beautiful Ft Myers Beach Condo ~ STEPS FROM BEACH

Come stay at this newly decorated waterfront condo close to the beach, shops, dining & marina all within a block from the condo. The condo is located on the so end of Ft Myers Beach with pristine baby powder beaches & Lovers Key State Park is a short drive or bike ride away. FMB is on Estero Island & is 7 miles long. You will be able to watch breathtaking sunsets at the beach, which is just at the end of the street & relax from your private lanai watching boaters & dolphins playing FMB#21-0219

11–18 Jul

$273 NZD per night

Guesthouse in Naples

4.8 out of 5 average rating, 297 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.

8–15 Dec

$189 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.

24 Nov – 1 Dec

$238 NZD per night

Guest favourite

Home in Captiva

4.97 out of 5 average rating, 107 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

31 Oct – 7 Nov

$1,393 NZD per night

Guest favourite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 316 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

17–24 Aug

$175 NZD per night

Guest favourite

Home in Fort Myers Beach

4.96 out of 5 average rating, 120 reviews

Coastal Oasis of Fort Myers Beach

Welcome to Fort Myers Beach Florida. This stunning, waterfront, contemporary ranch offers 5 bedrooms & 3 bathrooms. You will be impressed with the 2024 renovation from top to bottom. It will meet even the most discriminating of client's wish list. Pulling into the driveway you will notice beautiful, tropical landscaping. Entering the home through large French doors, you will be captivated by the elegant decor & immediate views of the stunning infinity pool and deep canal.

7–14 Dec

$1,873 NZD per night

Guest favourite

Home in Matlacha

5.0 out of 5 average rating, 142 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

30 May – 6 Jun

$865 NZD per night

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!

12–19 Jul

$214 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 193 reviews

Mermaid Oasis

Ft Myers beach Bonita Mermaid Oasis’s dream getaway! 1 bedroom King bed , full kitchen, spacious living room, sofa sleeper couch, beautiful balcony. Bathroom with a Jacuzzi tub, walk-in shower, private toilet area. The beautiful bay and pool invite you to come play. Flippers 5-star restaurant on the property. You can enjoy water sports long walks on Lovers Key Beach across the street. Only minutes to Bonita Naples and Ft. Myers beach, reviews say it all!

12–19 Mar

$707 NZD per night

Guest favourite

Home in Naples

5.0 out of 5 average rating, 127 reviews

Peaceful Gulf Access, Kayaks, Bikes, ebikes

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean.

3–10 Dec

$400 NZD per night

Holiday rentals for every style

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Popular amenities for Estero Island waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Guest favourite

Apartment in Caloosahatchee

4.86 out of 5 average rating, 140 reviews

The Cape (1) /Gulf access.

24 Apr – 1 May

$238 NZD per night

Apartment in Matlacha

4.63 out of 5 average rating, 136 reviews

Grouper Room in Matlacha * Redfish is open!

20–27 Oct

$209 NZD per night

Guest favourite

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 15 reviews

Your Home at the Beach!

10–17 Jan

$494 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

$304 NZD per night

Guest favourite

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 6 reviews

Sun and fun! Adorable 1 bedroom condo on the beach

19–26 Mar

$668 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 72 reviews

The "Tommy" Suite, 400 yards from The Gulf!

13–20 Aug

$441 NZD per night

Guest favourite

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 8 reviews

Lover's Key at Siesta Dreams

1–8 Oct

$391 NZD per night

Guest favourite

Apartment in Saint James City

4.93 out of 5 average rating, 84 reviews

Island Castaway--Free Kayaks

22–29 Apr

$228 NZD per night

Waterfront house rentals

Guest favourite

Home in Cape Coral

4.99 out of 5 average rating, 175 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

9–16 Sep

$982 NZD per night

Guest favourite

Home in North Fort Myers

4.93 out of 5 average rating, 123 reviews

Waterway Cottage in Historic N. Fort Myers Florida

25 May – 1 Jun

$233 NZD per night

Guest favourite

Home in Caloosahatchee

4.98 out of 5 average rating, 195 reviews

Dolphin beach house 2

3–10 Dec

$1,249 NZD per night

Guest favourite

Home in Cape Coral

4.96 out of 5 average rating, 108 reviews

Cozy in the Cape, Water views & private salt pool.

2–9 Oct

$346 NZD per night

Guest favourite

Home in Cape Coral

4.99 out of 5 average rating, 211 reviews

Gulf access waterfront heated pool

1–8 Aug

$294 NZD per night

Guest favourite

Home in Fort Myers

4.94 out of 5 average rating, 120 reviews

Paradise on Estero Bay

4–11 Oct

$723 NZD per night

Guest favourite

Home in Cape Coral

4.98 out of 5 average rating, 117 reviews

Vacation in Paradise

8–15 Sep

$274 NZD per night

Guest favourite

Home in Matlacha

4.98 out of 5 average rating, 184 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

21–28 May

$355 NZD per night

Waterfront condo accommodation

Condo in Naples

4.85 out of 5 average rating, 156 reviews

Ground Floor, A+ Location Club Membership Included

2–9 Aug

$228 NZD per night

Guest favourite

Condo in Naples

4.87 out of 5 average rating, 218 reviews

Park Shore Walk to Beach!

3–10 Aug

$378 NZD per night

Guest favourite

Condo in Naples

4.91 out of 5 average rating, 146 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

17–24 Dec

$722 NZD per night

Guest favourite

Condo in Fort Myers Beach

5.0 out of 5 average rating, 32 reviews

FMBSteps away from Gulf, pool Fabulous 2B/2B condo

3–10 Aug

$578 NZD per night

Guest favourite

Condo in Fort Myers Beach

4.93 out of 5 average rating, 27 reviews

Beachfront Lovers Key Beach Club Condo 1002

21–28 Sep

$335 NZD per night

Guest favourite

Condo in Fort Myers Beach

4.98 out of 5 average rating, 48 reviews

Santa Maria #410, 2 Story THouse, Fresh Remodel

20–27 Oct

$515 NZD per night

Guest favourite

Condo in Fort Myers Beach

5.0 out of 5 average rating, 27 reviews

Owner Managed | 3Bed 2Bath Beachfront Condo | Pool

23–30 Sep

$822 NZD per night

Guest favourite

Condo in Punta Gorda

4.95 out of 5 average rating, 37 reviews

One bedroom condo overlooking Harbor with Pool

5–12 Aug

$289 NZD per night

Destinations to explore