Stunning OCEANFRONT home w/gorgeous beach views. Walk the beach to Times Square
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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The host requires you to complete the following before checking out:
Remove personal items and take out the rubbish
Turn off the lights
Ensure no beach items are left outside the garage and all garage doors are closed
Failure to complete these may result in a negative review from the host.
Only registered guests are allowed on property. No other overnight guests are allowed. Unregistered guest visits, please contact owner.
No Parties allowed! Town noise ordinance in force. Fines can be imposed. Quite hours are 10 p.m - 7:00 a.m. Please respect neighbors
Any/all items in house are property of the owners. Do not remove any items or property from the house, except for using beach items to/from beach.
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number R260056
About the area
Fort Myers Beach
Located in Fort Myers Beach, this holiday home is on the beach. Shoppers can check out Coconut Point Mall, while everyone can enjoy the natural beauty of Estero Boulevard Beach and Bonita Springs Public Beach. Check out an event or a game at Lee Health Sports Complex, and consider making time for Hertz Arena, a top attraction not to be missed. With jet skiing, snorkelling and waterskiing nearby, you'll find plenty of adventures in the water.
Fort Myers, FL (RSW-Southwest Florida Intl.) - 43 min drive
Restaurants
License to Chill Bar - 16 min walk
Lah De Dah Beach Bar - 15 min walk
The Whale - 14 min walk
Parrot Key Caribbean Grill - 6 min drive
Marina Cantina - 6 min drive
Frequently asked questions
Is 15% off for stays before mid April-OCEANFRONT-Wide beach & sunset views pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Stunning OCEANFRONT home w/gorgeous beach views. Walk the beach to Times Square?
As of 9 Apr 2026, prices found for a 1-night stay for 2 adults at Stunning OCEANFRONT home w/gorgeous beach views. Walk the beach to Times Square on 12 Apr 2026 start from £748, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at 15% off for stays before mid April-OCEANFRONT-Wide beach & sunset views?
On-site parking is available at the property.
What time is check-in at 15% off for stays before mid April-OCEANFRONT-Wide beach & sunset views?
Check-in begins at 4:00 PM.
What time is check-out at 15% off for stays before mid April-OCEANFRONT-Wide beach & sunset views?
Checkout is at 10:00 AM.
Where is 15% off for stays before mid April-OCEANFRONT-Wide beach & sunset views located?
Nestled on the beach, this Fort Myers Beach holiday home is steps from Estero Boulevard Beach and 2 mi (3.2 km) from Key West Express. Crescent Beach Family Park and Bay Oaks Recreation Center are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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).
Jaclyn G.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 9 Apr 2026
Thank you for your great review, Jaclyn. We apologize for any inconvenience with the garbage cans not being located in the garage during your stay. While garbage is picked up weekly, they were moved out to prevent smells since temperatures are rising at the beach. However, we have since moved them back into the garage for our guests convenience. Thanks again and we hope you will consider our property again in the future should you return to Fort Myers Beach. All our best! Deb, Tom and Kahley.
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!
jill r.
Stayed 7 nights in Feb 2026
Response from VrboOwner on 23 Feb 2026
Wow! Thank you so much for your glowing review, Jill! We can't tell you how very pleased we are to hear you enjoyed your stay. You were all such wonderful, respectful guests and we would happily welcome you back again anytime. All our very best, Deb and Tom
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
Jason P.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 5 Apr 2026
Hi Jason!
What an incredible review! Wow! We cannot tell you how very pleased to read all the wonderful comments you and your friends/family have shared. We truly hope you and your family/friends will consider staying with us again should you return to beautiful Fort Myers Beach in the future. All our very best, Deb, Tom and Kahley.
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.
Carey J.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 9 Apr 2026
Thank you for your great review, Carey. We are so pleased to hear your daughter enjoyed the little birthday surprise and you all enjoyed your stay. We would happily welcome you and your family back to stay with us again should you return to Fort Myers Beach. All our best! Deb, Tom and Kahley