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Dock Holiday Your "backyard" is Bayfront with spectacular, serene views, pool and plenty of seating for the ultimate relaxation experience

House
Plenty of SeatingKing Primary Bedroom private deckBeautiful Pool Looking to the Bay288 Ostego DriveBreakfast Bar
Dock Holiday
1 Promotions available
Sleeps 8
3 Bedrooms
2 Full Baths
1 Half Baths

Top Reasons to Book Dock Holiday:

*Bay Front Home with Gorgeous Views and Pool

* Wine Fridge, Keurig, Multiple Balconies, and Gas Grill

* 569 Yards to Beach Access #33

* 0.6 Miles to Times Square

* Professionally Managed

Welcome to Dock Holiday. This beautiful bay front home features large picture windows throughout the home and beautiful wood flooring on the main level. Spend your days floating in the large, heated pool and enjoying the beautiful bay views. There is plenty of room for the whole family in this bright and airy three-bedroom home. A large white kitchen with a wine fridge offers plenty of prep space to whip up a delicious meal. A picturesque window frames the dining room with a table that seats up to eight guests. The living area features cozy seating and a recliner. There is also a desk and French doors leading to the front balcony. One the other side of the living room are sliding glass doors that welcome guests to a large balcony overlooking the pool and bay. Upstairs guests will find the primary bedroom with a king bed and private balcony. The attached bath incudes double sinks, garden tub, and walk-in shower. There is also a queen bed in one guest bedroom and a twin daybed with trundle in the other bedroom. Including a sofa sleeper in the living room with a memory foam mattress this home sleeps up to 8 guests comfortably. Come visit Dock Holiday and make everlasting memories.

The Bed Set-Up:

Main Level:
Living Room: Sleeper Sofa

Upstairs:
Primary Bedroom: King Bed with En Suite

Guest Bedroom: Queen Bed

Guest Bedroom: Twin Daybed with Trundle

*This property does not allow parties of adults under the age of 25.*

**The dock is currently unavailable. Please excuse this inconvenience. **

Area Activities:

Welcome to Fort Myers Beach! There are multiple state parks nearby that are waiting for your adventures. Jump on the trolley to take you south to the secluded Lover's Key State Park or go north to Bowditch Point Park. The Fish Tale Marina offers boat rentals and dockage for those wanting to get out on the water. Travel around the island in style in a rented Moke or golf cart. Trolley service is also available from Estero Boulevard to the Times Square area, the central hub of Fort Myers Beach. Several restaurants, shops, and bars have come back since the hurricane. If a day trip is what you are looking for check out the Key West Express for an unforgettable trip to Key West. Don’t forget to see Sanibel Lighthouse which is less than 15 miles away! Please note that the area is currently rebuilding after Hurricane Ian. Despite the changes, the island continues to get better and better, inviting you to bask in the sun, sand, and amazing sunsets once again. As local restaurants continue to reopen, you'll have lots of opportunities for entertainment and dining experiences. We're excited to welcome you back.

288 Ostego Dr.
FMB STR License 19-0504

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Top 4 Amenities
Water View
Beach Access
Private Pool
Short Walk to Beach

Room Arrangements

Primary bedroom

1 King Bed

Primary bedroom with king bed , private deck and ensuite

Guest Bedroom

1 Queen Bed

Guest bedroom with Queen Bed

2nd Guest Bedroom

1 Twin Daybed Bed

1 Twin Trundle Bed

Twin Daybed with Trundle Bed

Sleeper Sofa

1 Sofa Sleeper Bed

sofa sleeper in common area

Primary bathroom

Primary bathroom with Bath tub, walk in shower , and Bidet

Guest Bathroom

guest bathroom adjacent to guest bedrooms with Tub/ shower enclosure

Half Bath

Half bathroom on the mani floor

Availability
Location
55 Reviews
5.0  

Stayed February 2026

5/5 
"This place was absolutely amazing. It was beautiful, location was great. A maintenance issue was resolved quickly. There are two things I would recommend. The first is to have a bottle of all purpose cleaner available for guests. The second thing is to update the listing to say you have a Kureig. Would stay again. "

Stayed February 2026

5/5 
"My family and I absolutely love staying at this place. It’s very close and walkable to all the fun things to do and restaurants in the area. Our kids love the pool as it was heated, so we spent a lot of time out there."
Allison
Customer Relations Representative
Thank you so much Matt! Happy to hear dock Holliday worked so well for you and your family l! The pool area and the view is really quite something ! We would love to host you again ! Sun Palace Vacations

Stayed January 2026

5/5 
"Overall great stay and location private yet walking distance to everything. We had an issue with the pool heater which was revolved a couple of days into the stay. Would book again."
Allison
Customer Relations Representative
Thank you for your review! We’re glad you enjoyed the private setting and convenient walking distance to everything. We apologize again for the pool heater issue and appreciate your patience while it was resolved. We’re happy to hear you’d book again and would love to host you in the future!
Available Promotions

Adjust dates according to the promotion description and the discount will be applied to the total.

1 Promotions available