Stunning OCEANFRONT home w/gorgeous beach views. Walk the beach to Times Square

Fort Myers Beach, Florida
$1313 avg/night
Minimum Stay 4 Nights
Bed 5

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 4 nights

Min Stay

Please note: We were a 5-star Premier Host prior to Hurricane Ian destroying our two properties on Fort Myers Beach in 2022. This property is a brand-new home built on the same property as before.

FMB Registration #R260057

Welcome to Calypso Key! Located oceanfront and within walking distance to the popular Times Square area. Calypso Key is a pretty, beachy blue two-story cottage style beach house with 5 bedrooms, 5 ½ baths and a queen size cabinet murphy bed.
>The enclosed lowest-level of the house is the garage with parking inside for 2 cars and outside parking for 1 car.

As you make your way up to the main floor living area via the inside stairway or the elevator located in the lower-level area, you'll be greeted by Calypso Key's light, bright pretty blue decorated living/dining/kitchen area with a 65 Roku TV w/Sonos soundbar and a wall of recessed sliding glass doors that can be opened to a spacious beachfront covered lanai’ with stunning oceanfront views. This is indoor/outdoor living at its best! The large lanai' is the perfect gathering spot for friends and family to watch a sunrise as you enjoy a morning cup of coffee and watch for dolphins swimming by or gather together for evening cocktails with a front row seat to catch one of FMB’s gorgeous, iconic sunsets!

With oceanfront views available from almost every room, you'll know you are truly on the beach!

The nice size, fully equipped kitchen has everything a cook will need with a full-size oven/induction cooktop, microwave drawer, dishwasher, refrigerator/freezer, large pantry, spacious beachy blue colored island with seating for 4 and a large coastal style dining table with seating for up to 10. Coffee lovers will enjoy (2) Keurig coffee makers, a 12-cup drip coffee maker and coffee grinder.

As you make your way up the coastal inspired shiplap covered stairway to the 3rd floor, you'll find 4 more bedrooms (1 king bed, 3 queen beds) each with its own private ensuite bathroom, 43” TV with soundbar, and beach views. All but one bedroom has an outdoor balcony area with 2-adirondack counter height chairs accessible via the bedroom’s sliding glass doors.

Location: This home sits on a wide, expansive area of the white sandy beach that is never overly crowded. You can rest assure you will always be able to find the perfect spot to setup for a perfect beach day of sunbathing, swimming, building sand castles, spotting dolphins, shell hunting and just relaxing.

Speaking of beach days, you have 3 beach carts, 12 beach chairs, 2 large coolers, 3 beach umbrellas and an easy setup beach tent available. After a day at the beach, stop by the shared outdoor surfboard styled shower (shared with sister property guests in the green house) to rinse off sandy toes.

Dining out and entertainment options Just step out your door and take a leisurely 15-minute stroll along the beach or hop aboard one of several free trolleys to Times Square area. There you will find a variety of dining options and live music. Several popular restaurants/bars are The Whale, SOB's (Smokin Oyster Bar), Nervous Nelli's, Matanza's on the Bay, Wahoo Willie's, Snug Harbour, Lighthouse Bar or visit Margaritaville's bar/restaurants which are open to the public. A popular spot, especially on a partly cloudy or clear evening, is their huge open air, upper deck with lots of conversation seating areas and firepits or grab a seat around the large bar, order up a signature Margarita and prepare to be awe-inspired as you witness one of Fort Myer's Beach iconic sunsets.

Rather grill out and eat at home We've got you covered with a 5-burner Napoleon gas grill, dining tables and chairs. Open the two garage doors facing the ocean and you have 10- Adirondack chairs set directly in the sand. Slap some steaks on the grill, grab a cocktail and soak up the sun with a game of corn hole or volleyball.

This home is perfect for families or couples looking for an oceanfront property, within walking distance to shopping, bars/restaurants and entertainment (Publix grocery store is 2 miles down the road on Estero).

You can rest assure knowing as prior 5 star premium hosts (before Hurricane Ian's destruction), you will receive great customer service and stay in a beautiful property with all the amenities. This beautiful beachfront home truly has it all and we welcome you to come see for yourself.

Need more or less space Check out our 4 bed, 4 1/2 bath sister beachfront property, Sandy Cay on Vrbo. Discounted rate available if you rent both properties https://t.vrbo.io/HvRxyV3Dz0b

Please Note: Due to ongoing rebuilding efforts around the island, Coastal Cottages Property owners will not be responsible for any construction that may be happening next to the property or in the surrounding area or on the beach. Following hurricanes Ian, Milton, and Helene, guests should anticipate ongoing construction throughout the island. This could include construction noise, nearby building projects, increased traffic, or beach restoration efforts. We want to ensure full transparency—construction is beyond our control, and we will not be offering compensation or refunds due to these conditions. By booking, guests understand, acknowledge and accept the possibility of construction-related impacts during their stay.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels On The Beach
  • DINING

    Dining Table
  • SAFETY

    Fire Extinguisher No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling Unit Size: 2000 Sq Ft (186 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Kitchen Island Lobster/crab Pot Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Outdoor Furniture
  • BATHROOMS

    5.5 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • THINGS TO DO

    Jet Skiing Nearby Parasailing Nearby Power Boating Nearby Snorkeling Nearby Swimming Nearby Water Skiing Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books Games Stereo Smart TV
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware
  • LOCATION HIGHLIGHTS

    Near The Ocean On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 Stairs To Reach Property Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Tile Flooring In Public Areas Visual Alarms In Hallways Well-lit Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Availability

Review Review

  • Carey J.

    Submitted Apr 6, 2026

    Stayed Apr 2, 2026

    Beautiful beach front property with amazing views! We were very pleased with the home and location! The elevator was a lifesaver with heavy suitcases & groceries as the home has 3 levels. Host had birthday surprise waiting for our daughter when we arrived. Definitely would recommend staying at this beautiful property.

  • Jason P.

    Submitted Apr 4, 2026

    Stayed Mar 27, 2026

    This home was absolutely gorgeous! When other reviews say it’s fully stocked and ready for you, they are not exaggerating. There were plenty of beach chairs, sand toys, and all the cooking and serving ware you could need—even a setup in the garage wet bar area so you don’t have to carry anything down from the main level.The bedrooms were beautifully decorated, and each connected bathroom was fully stocked and ready for us. I especially appreciated the thoughtful details throughout the home, like the different mood lighting options and clearly labeled light switches, which made everything easy and convenient.The hurricane windows were a standout feature—we loved being able to open them during the rain and still enjoy the weather.Honestly, all you need to bring is your swimsuit and food! This is definitely a place we would return to for more family memories.------We had an incredible stay at this beachfront property. The views of the ocean were absolutely stunning. Waking up and seeing the water each morning was a highlight of the trip.The home itself was spotless and very well maintained, which made settling in easy and comfortable. There was more than enough space for our entire family, with room for everyone to relax without ever feeling crowded.We especially appreciated the thoughtful amenities. Having a washer and dryer on-site was extremely convenient, and the elevator made transporting luggage and larger items effortless.Everything you could possibly need

  • Jaclyn G.

    Submitted Apr 2, 2026

    Stayed Mar 15, 2026

    This was a great place for our trip to Fort Myers Beach! Communication was great with the property manager and the few issues we had were solved quickly! The only thing to note is that the trash cans are not located in the garage as mentioned in the welcome packet and contract. They're located in front of the sister property (green house).

  • jill r.

    Submitted Feb 22, 2026

    Stayed Feb 13, 2026

    This is by far the best place we have rented and we have rented many five star places! This one deserves ten! The house itself is beautiful and brand new, the view is amazing and the beach is so big and perfect for walking miles. So many touches in the house to make it feel like home from soft blankets, laundry baskets, games for the kids to all the beach necessities. It's a complete rental how I wish they all would be. It was super clean which is very important to me and the kitchen had everything we needed and more. The hosts were very quick to respond and very thoughtful too. We arrived to a birthday cake, champagne and balloons for the birthday we were celebrating. That's the kind of love and care they are putting into making this rental a great find. And yes, this is a REAL review we did not know the hosts and we are so happy we took a risk to rent this new house. It would be so fun for two families to rent this one and the one behind it together. We plan to return!

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Total

Includes taxes and fees
$1,383+
View details