Mornings
Walk, don't drive, to the sand.
Beach Access #16 is at the end of Dakota Ave. You can carry chairs and a cooler down in one trip and come back for lunch without moving the car.
Mid-island Fort Myers Beach
A quiet mid-island street, two minutes from the Gulf.
Fort Myers Beach sits on Estero Island — seven miles long, one road down the middle, and the part of the island you pick changes the whole trip. Docked at Dakota is mid-island at 240/244 Dakota Ave, Fort Myers Beach, FL: a residential street with a heated pool, four free parking spaces, and Beach Access #16 about a two-minute walk away.
What "mid-island" actually means for your week
The north end of Fort Myers Beach, around Times Square, is where the crowds, the bars, and most of the traffic are. The south end is quieter but further from the action. Mid-island sits between the two, which is why it tends to suit families best.
Afternoons
A heated pool for the in-between hours.
Sun, wind, or a bit of both — the pool beside the house covers the afternoons when nobody wants another beach shift, and it stays usable outside high summer.
Evenings
Both ends of the island within reach.
Times Square and the north end for a busier night out, Santini Plaza and the south end for something quieter, and the grill at the house when nobody wants to go anywhere.
Nights
A residential street, not a strip.
Dakota Ave is a street of houses rather than a commercial stretch, which matters when you have small children going to bed early.
Where mid-island sits on Estero Island
Estero Island runs roughly north to south, with Estero Boulevard the only road down it. Most Estero Island vacation rentals fall into one of three stretches, and they make for quite different weeks.
North end
Times Square and the crowds.
Where the restaurants, bars, shops and most of the foot traffic are. Good for an evening out, busy to live on, and the slowest traffic on the island in season.
Mid-island
Residential streets, short beach walks.
Numbered beach accesses every few streets, houses rather than high-rises, and both ends of the island a short drive away. This is where Dakota Ave is.
South end
Quietest, and furthest from everything.
Calmest stretch of sand, with Santini Marina Plaza for groceries and meals and Lovers Key just beyond the bridge — but a longer run to the north end.
The deciding factor
How far you walk to sand.
Island beach parking is charged by the hour or by the day, so a rental you can walk from saves both money and the daily hunt for a space. Beach Access #16 is two minutes from the door here, and parking at the house is free.
What the house itself includes
A new 2025 build with two complete, mirrored sides — unusual for the island, and the reason larger groups can travel together here without sharing a single kitchen.
- New 2025 side-by-side duplex
- 2-minute walk to Beach Access #16
- Heated pool
- Book one side or both sides
- Fully stocked kitchens
- Washer and dryer in each unit
- Dedicated workspace with monitor, keyboard, and mouse
- Beach chairs, umbrella, cooler, and beach cart/wagon
- Free parking
- Mid-island Fort Myers Beach location
Book the layout that matches your group
Three bedrooms for one family, or six when two families travel together.
Best for groups View Whole House
Docked at Dakota House
Both mirrored sides together: two living rooms, two kitchens, four baths, two laundry setups, separate entrances, and a private pool experience for the group.
6Bedrooms
4Baths
12Guests
Private 3-bedroom side View Sunset
Docked at Dakota Sunset
A private 3-bedroom side with a full kitchen, washer and dryer, workspace, beach gear, grill access, and the shared heated pool.
3Bedrooms
2Baths
6Guests
Mirrored 3-bedroom side View Sunrise
Docked at Dakota Sunrise
The matching 3-bedroom retreat with the same easy beach walk, coastal interiors, fully stocked kitchen, washer and dryer, workspace, and shared pool access.
3Bedrooms
2Baths
6Guests
What guests say about the location
The quiet street and the short beach walk are the two things reviews mention most.
★★★★★
Perfect for our families. My sister and I decided to rent the whole house. My family was on the one side and her family on the other. It worked out great, as we were together but also had enough space on our own. We enjoyed the short walk to the beach and had the best time relaxing by the heated pool. The location is great. It's quiet and peaceful but when we needed restaurants and nightlife it's so close to downtown and Santini Plaza!! It was perfect. We can't wait to come again.
★★★★★
We had a wonderful stay at this home in Fort Myers from Friday through today. The house was very comfortable, spacious, and exceptionally clean. It was perfect for our family with kids, and the pool was also great and very comfortable for everyone to enjoy. The location was excellent, very close to the beach — just a short walk of a few minutes, only about two blocks away. The host was extremely kind, attentive, and communicative throughout our stay. We truly enjoyed our time here and would definitely stay again. Highly recommended for families!
★★★★★
We had an amazing stay and couldn't recommend this place more. The layout was perfect, especially for a larger group—having separate spaces while still being together made everything so comfortable. The heated pool and patio area were a huge highlight and quickly became our favorite spot to relax. The walk to the beach was quick and easy, and the location itself was ideal—quiet and peaceful, yet close enough to restaurants, shops, and nightlife when we wanted to go out. The home was clean, well-maintained, and exactly as described. We would absolutely stay here again and would highly recommend it to families or groups looking for a great beach getaway!
Reviews from the property’s Airbnb listings, quoted in full.
Getting around from Dakota Ave
A few of the places guests tend to head for during a mid-island week.
Dakota Beach Access #16
The public beach access at the end of Dakota Ave, listed by the Town of Fort Myers Beach as Access #16. About a two-minute walk from the front door, so you can carry chairs and a cooler down in one trip.
Plan your visit — Town of Fort Myers BeachMound House
The island's museum and historic site, built over a Calusa shell mound and preserving close to 2,000 years of cultural and environmental history. One of the few indoor options on the island, so it is the usual answer to a rainy morning with kids.
Plan your visit — Mound HouseMatanzas Pass Preserve
A free 60-acre preserve on the bay side with boardwalk trails through mangroves and maritime oak hammock, plus the Fort Myers Beach Historic Cottage at the entrance. The shadiest walk on the island and the closest nature stop to Dakota Ave.
Plan your visit — Lee County ParksLovers Key State Park
A Florida state park just south of Estero Island with a much quieter beach, mangrove paddling trails, a discovery centre, and regular sightings of dolphins, manatees and shore birds. The standard mid-week change of scene.
Plan your visit — Florida State ParksRates and availability
Rates change with the season and with how long you stay, so the live calendars are the only place with an accurate total. Pick your dates on either link below for an exact quote, or call and we will price it with you.
Docked at Dakota House
6 bed · 4 bath · sleeps 12
Docked at Dakota Sunset
3 bed · 2 bath · sleeps 6
Docked at Dakota Sunrise
3 bed · 2 bath · sleeps 6
Prefer to talk it through? Call Sea Gypsy Vacation Rentals on 239-463-0078.
Mid-island stay questions.
The practical things guests check before booking a week on Dakota Ave.
How far is the beach?
Dakota Beach Access #16 is about a 2-minute walk from the house at 240/244 Dakota Ave, so you can walk to the sand and back without moving the car.
Is the pool private?
The pool is private for your group when both sides are booked together. When only one side is booked, the pool is shared between the two units.
How many parking spaces are there?
The whole house includes four parking spaces. Each individual side, Sunset or Sunrise, includes two spaces. Parking is free and on site.
Can we rent both sides of Docked at Dakota?
Yes. Booking the whole house combines both 3-bedroom sides into one 6-bedroom, 4-bath stay for up to 12 guests, with two kitchens, two living rooms, and two laundry setups.
How much does it cost to stay?
Rates change with the season and with how long you stay, so there is no single nightly price. Enter your dates on the Sea Gypsy booking page or the Airbnb listing for an exact total, or call 239-463-0078 and we will price it with you.
How do we book?
Book direct through Sea Gypsy Vacation Rentals using the booking links on this site, or call 239-463-0078 if you would rather talk through dates. The same stays are also listed on Airbnb if you prefer to book there.
Stay mid-island this year.
A heated pool, a two-minute beach walk, and room for up to 12 guests when you take both sides.
Managed by Sea Gypsy Vacation Rentals · 240/244 Dakota Ave, Fort Myers Beach, FL