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Beachfront vacation rentals in Estero Island

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Top-rated beachfront rentals 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, 125 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

Jul 25 – Aug 1

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

Mar 10 – 17

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!

Jul 23 – 30

Home in Fort Myers Beach

4.86 out of 5 average rating, 59 reviews

2 Bedroom Beach House - Steps to Fort Myers Beach!

FMB Reg#22-0462; DBPR Rental License#DWE4607464 2 bed/2 bath house across the street from the beach, and is a piece of history - one of the homes that survived Hurricane Ian. We're confident you'll enjoy your stay at our beach house! Family owned since 1968. Clean/well cared for with nice landscaping. The island is recovering from the hurricane but Times Square is open for dining 3 miles away. Come soak up the sun & enjoy some relaxation at our home! 2 queen beds WiFi non-smoking Washer/Dryer

Jan 20 – 27

Home in Captiva

4.97 out of 5 average rating, 108 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

Jul 31 – Aug 7

Apartment in Cape Coral

4.87 out of 5 average rating, 141 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.

Apr 13 – 20

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.

May 23 – 30

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.

Nov 24 – Dec 1

Condo in Fort Myers Beach

5.0 out of 5 average rating, 6 reviews

Beach Villas #104 - Beach Front Condo 20% OFF

Spring24 Promo Code – 20% off any booking with a minimum of 5-night stay in April or May (excluding Memorial Weekend). Welcome to Estero Island Beach Villas #104, your delightfully decorated beachfront vacation in paradise! Located in the quieter North end of Estero Island, this two-bedroom, two-bath first-floor above-ground-level gulf-front condo has a 180-degree view of the Gulf of Mexico and the sugar sand beach Fort Myers Beach is famous for.

Dec 1 – 8

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.

Jul 15 – 22

Apartment in Fort Myers

4.98 out of 5 average rating, 96 reviews

2nd Floor Beachfront Condo Sanibel Harbour

You’ll love the beautiful sunsets on the Lanai over looking the beach on San Carlos Bay. Dolphins frequently play near this beach and can seen along with the other wildlife. Condo Hurricane Update The condo did just fine through the storm. The area around the building was damaged. However, they have done a great job cleaning and fixing things up. The condo beach has been groomed and is ready to enjoy, as well as the pool!

Dec 6 – 13

Condo in Fort Myers Beach

5.0 out of 5 average rating, 27 reviews

Owner Managed | 3Bed 2Bath Beachfront Condo | Pool

Welcome to GullWing 202! OWNER-MANAGED 3 bedroom, 2 bathroom condo on the widest stretch of white, sand beach on Estero Island. Relax and enjoy the sun on the beach or poolside while helping to support the rebuilding efforts in Fort Myers Beach! The pool is open complete with all new furniture and new BBQ grills. Publix and CVS are now open along with more and more restaurants.

Aug 17 – 24

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Popular amenities for Estero Island beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 6 reviews

Sun and fun! Adorable 1 bedroom condo on the beach

Jan 30 – Feb 6

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 39 reviews

Heated Pool Home steps to the beach

Jul 9 – 16

Home in North Fort Myers

4.8 out of 5 average rating, 5 reviews

Canal View Cottage

Jul 28 – Aug 4

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 20 reviews

Beach, pool time & fun times @ Blue Fish Lagoon

Jul 21 – 28

Home in Captiva

5.0 out of 5 average rating, 4 reviews

Turtle Escape: Pool, Beach & Fun!

Dec 12 – 19

Home in Placida

5.0 out of 5 average rating, 51 reviews

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

Dec 17 – 24

Condo in North Fort Myers

4.83 out of 5 average rating, 98 reviews

Ground Floor Lake-Front Condo on 5 ac private lake

Aug 4 – 11

Home in Cape Coral

5.0 out of 5 average rating, 11 reviews

A tropical boaters pet friendly paradise!

Aug 26 – Sep 2

Beachfront home rentals with a pool

Home in Captiva

4.91 out of 5 average rating, 102 reviews

Blue Laguna - Vacation in paradise!

Aug 27 – Sep 3

Cottage in Bokeelia

4.99 out of 5 average rating, 111 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Dec 30 – Jan 6

Home in Fort Myers Beach

5.0 out of 5 average rating, 3 reviews

Waterfront Island Oasis w/Heated Pool & Boat Lift!

May 15 – 22

Villa in Fort Myers Beach

4.89 out of 5 average rating, 28 reviews

Wischis Florida Home - Sunshine Beach

Jul 28 – Aug 4

Condo in Fort Myers Beach

5.0 out of 5 average rating, 32 reviews

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

Mar 24 – 31

Home in Fort Myers Beach

5.0 out of 5 average rating, 12 reviews

Island Oasis-dock, pool, 5 min walk to beach.

Nov 17 – 24

Condo in Bonita Springs

4.8 out of 5 average rating, 35 reviews

Stay With Us In Our Tropical Paradise Suite

Jul 20 – 27

Home in North Fort Myers

4.93 out of 5 average rating, 73 reviews

Lazy Palm Retreat Heated Pool Jacuzzi Gulf Canal

Sep 23 – 30

Private beachfront home rentals

Apartment in Fort Myers Beach

4.93 out of 5 average rating, 42 reviews

Ready Post Ian! Owners on HGTV! Private Beach Path

Aug 28 – Sep 4

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 8 reviews

Lover's Key at Siesta Dreams

Jul 8 – 15

Home in Fort Myers Beach

4.9 out of 5 average rating, 40 reviews

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

Sep 16 – 23

Home in Naples

5.0 out of 5 average rating, 44 reviews

Stylish & Cozy ★ Walk to Beach ☀ Pool ♕ King Beds

Dec 1 – 8

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 29 reviews

Beachfront Lovers Key Beach Club Condo 802

Nov 2 – 9

Camper/RV in North Fort Myers

4.95 out of 5 average rating, 38 reviews

Waterways Escape

Jun 10 – 17

Home in Cape Coral

5.0 out of 5 average rating, 22 reviews

Cape Coral Paradise, Waterfront, Patio, Pool, Spa

Jul 7 – 14

Apartment in Bonita Springs

4.97 out of 5 average rating, 92 reviews

Beach/Sunset Bay/Sunrise Relax/Island Living

Sep 14 – 21

Destinations to explore