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Beachfront holiday rental in Estero Island

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Top-rated beachfront accommodation in Estero Island

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

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Home in Fort Myers

4.82 out of 5 average rating, 124 reviews

Blue Beach Bungalow

3 large bedrooms (2 queens, one king) plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics, and all the creature comforts you can imagine

7–14 Sep

$915 NZD per night

Home in Fort Myers Beach

5.0 out of 5 average rating, 4 reviews

Welcome To Pleasant Paradise

Welcome to Pleasant Paradise where you will take in the beautiful views of the Gulf of Mexico from your private balcony. This 1-bedroom condo is the perfect vacation getaway. It is located in the Estero Beach and Tennis Club at the south end of the island. This is a 7 NIGHT MINIMUM rental property, during high season ( January through April) it must be a Saturday - Saturday, after the 7th night you can stay however long. I would like to note that there is still some construction going on at

2–9 Nov

$553 NZD per night

Guest favourite

Cottage in Saint James City

5.0 out of 5 average rating, 26 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!

28 Aug – 4 Sep

$298 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

Apartment in Cape Coral

4.86 out of 5 average rating, 140 reviews

The Cape (1) /Gulf access.

Why waste your vacation time and money on taxis. This beautiful newly renovated apartment is located just blocks from downtown Cape Coral. Less than 10 minutes walk to bars, restaurants and stores. Use the bicycles we provide for guests to bike around the Cape. 5 mins drive to Cape Coral beach/yacht club.Rent a boat for your vacation and tie up at your own personal dock. 10 minutes boat ride to river.The space is for 2 adults and 2 children. Not for 3-4 adults. Fastest internet available.

24 Apr – 1 May

$238 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

If you are craving some sunshine and blue waters, come on down! Morning walks with your toes in the sand set the tone for another day in Paradise. Spend the day in the surf and sun, then finish off another perfect day quietly entranced by another unique and spectacular sunset. Whether you want to relax on the balcony and enjoy looking at the gulf, play in the surf, lay out on the beach or pick shells, lounge by the pool or enjoy a few rounds of tennis and pickle ball, you won't be bored.

7–14 Nov

$408 NZD per night

Guest favourite

Home in Fort Myers Beach

5.0 out of 5 average rating, 5 reviews

Happy Horizons

The house is exclusively for adults only. The balconies offer breathtaking views of the Gulf of Mexico, where you can spot many species of colorful birds, such as pelicans, egrets, osprey, and herons, as well as dolphins swimming in the surf. You can take early morning, afternoon or sunset walks on the sand, and dine or enjoy cocktails on the gulf side decks overlooking the beach and Gulf. Watching the beach sunsets is an absolute treat! There is something for everyone at your property.

9–16 May

$904 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

White Cap Beach condo is just steps away from the gulfs white sandy beach. Relax, unwind, and create beautiful memories in this 2b/2b condo! The master bedroom oasis has a king size bed, full bathroom, private balcony, and a streaming TV. The second bedroom boasts a beachy feel with two twin beds and a streaming TV. The living room has a pull out queen sofa and a new 60 inch 4k TV. The fully loaded kitchen contains all your cooking needs. Enjoy Gulf views from your front balcony.

3–10 Aug

$578 NZD per night

Condo in Fort Myers Beach

5.0 out of 5 average rating, 4 reviews

50 Shades of White - Gullwing #805

Spring24 Promo Code – 20% off any booking with a minimum of 5-night stay in April or May (excluding Memorial Weekend). Welcome to 50 Shades of White is a privately owned unit within the Gullwing resort and has undergone renovations in 2023 to modernize and differentiate it from other units at the resort. Renovations include all new kitchen cabinets, countertops, appliances, and sinks, with new vinyl flooring and modern light fixtures throughout the unit.

11–18 Sep

$989 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.

26 Jul – 2 Aug

$425 NZD per night

Home in Fort Myers Beach

5.0 out of 5 average rating, 4 reviews

Come enjoy Flip Flops Forever

We're back and better than ever! You've had to put your vacation at the Beach on hold, we are ready for you now! While our rental homes may look a little different, yards may not be as lush as Fort Myers Beach rebuilds, we can tell you that all our homes that have been either renovated or rebuilt and have been inspected thoroughly to meet your needs. When choosing your home, please be sure to read the descriptions carefully.

15–22 Jul

$485 NZD per night

Home in Fort Myers Beach

5.0 out of 5 average rating, 3 reviews

Waterfront Island Oasis w/Heated Pool & Boat Lift!

***BI-WEEKLY, MONTHLY & SEASONAL RENTALS ALLOWED*** Come enjoy this waterfront coastal getaway. Equipped with an infinity edge pool, dock with a motorized boat lift, and outdoor dining/grill area. Enjoy your morning sunrise over the water on the widest canal on the island. The stylish interior is spacious with a mix of mid century modern and coastal flare. This is truly your home away from home.

3–10 Oct

$1,077 NZD per night

Holiday rentals for every style

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Popular amenities for Estero Island beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Apartment in Matlacha

4.81 out of 5 average rating, 43 reviews

Studio#3 The Heart of Matlacha-kayaking access

4–11 Aug

$221 NZD per night

Guest favourite

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 39 reviews

Heated Pool Home steps to the beach

21–28 Mar

$851 NZD per night

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 19 reviews

Beach, pool time & fun times @ Blue Fish Lagoon

3–10 Dec

$976 NZD per night

Guest favourite

Home in Captiva

5.0 out of 5 average rating, 25 reviews

Private Island Luxury * Pool * Dock * Club Access

8–15 Sep

$1,273 NZD per night

Guest favourite

Home in Cape Coral

5.0 out of 5 average rating, 11 reviews

A tropical boaters pet friendly paradise!

19–26 Aug

$780 NZD per night

Guest favourite

Home in Placida

5.0 out of 5 average rating, 50 reviews

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

30 Dec – 6 Jan

$1,280 NZD per night

Home in North Fort Myers

4.75 out of 5 average rating, 4 reviews

Canal View Cottage

26 Nov – 3 Dec

$259 NZD per night

Guest favourite

Home in Cape Coral

4.91 out of 5 average rating, 34 reviews

The Doghouse

6–13 Aug

$529 NZD per night

Beachfront home rentals with a pool

Guest favourite

Home in Captiva

4.91 out of 5 average rating, 102 reviews

Blue Laguna - Vacation in paradise!

18–25 Apr

$1,471 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

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

Villa in Fort Myers Beach

4.89 out of 5 average rating, 28 reviews

Wischis Florida Home - Sunshine Beach

24 Sep – 1 Oct

$1,359 NZD per night

Guest favourite

Apartment in Fort Myers

4.98 out of 5 average rating, 95 reviews

2nd Floor Beachfront Condo Sanibel Harbour

19–26 Apr

$1,321 NZD per night

Guest favourite

Condo in Bonita Springs

4.84 out of 5 average rating, 32 reviews

Stay With Us In Our Tropical Paradise Suite

20–27 Jul

$288 NZD per night

Home in Fort Myers Beach

5.0 out of 5 average rating, 12 reviews

Book 4 nights get 5th free/dock/pool/walk to beach

10–17 Nov

$1,906 NZD per night

Guest favourite

Home in Bonita Springs

4.94 out of 5 average rating, 34 reviews

Seaside Escape steps from Bonita Beach

20–27 Jun

$1,434 NZD per night

Private beachfront home rentals

Home in Fort Myers Beach

4.86 out of 5 average rating, 58 reviews

2 Bedroom Beach House - Steps to Fort Myers Beach!

9–16 Apr

$719 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

Home in Bonita Springs

4.8 out of 5 average rating, 5 reviews

Beach Haven: Sun, Sand, Serenity

2–9 Nov

$1,839 NZD per night

Guest favourite

Apartment in Fort Myers Beach

4.93 out of 5 average rating, 42 reviews

Ready Post Ian! Owners on HGTV! Private Beach Path

18–25 Sep

$608 NZD per night

Guest favourite

Home in Fort Myers Beach

4.9 out of 5 average rating, 40 reviews

200ft From Beach.. 2 Bed 2 bath.. Remodeled SPA

6–13 Feb

$819 NZD per night

Guest favourite

Campervan/RV in North Fort Myers

4.95 out of 5 average rating, 38 reviews

Waterways Escape

23–30 Aug

$183 NZD per night

Guest favourite

Home in Cape Coral

5.0 out of 5 average rating, 20 reviews

Cozy Doll House at Yacht Club CC

11–18 Jul

$225 NZD per night

Apartment in Naples

5.0 out of 5 average rating, 3 reviews

Westshore 1201 at Naples Cay

2–9 Jun

$897 NZD per night

Destinations to explore