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.*
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
Show less *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.*
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
Water View
Beach Access
Private Pool
Short Walk to Beach
Amenities
Essentials
Air ConditioningBed LinensDryerEssentialsTowelsHair DryerHangersHeatingLaptop FriendlyLock on Bedroom DoorWasher
Kitchen
Cooking BasicsDishes & SilverwareMicrowaveRefrigeratorToasterStoveBlenderDrip Coffee MakerDishwasherOvenKeurig Type Coffee Maker
Accomodations
Mid Stay Cleaning: OptionalBathtubEnsuite Bath
Attractions
ChurchesFestivalsHealth Beauty SpaMarinaMuseumsPlaygroundRestaurantsSynagoguesWater ParksZoo
Entertainment
Satellite or CableTelevisionHD TV Cable
Home Safety
Fire ExtinguisherSmoke Detector
Facility
Free ParkingWireless Internet
Leisure
Bird WatchingBoatingMiniature GolfOutlet ShoppingPhotographyShellingShopping
Local
Fitness CenterHospital
Sports
CyclingDeepSea FishingFishing - BayGolfJet SkiingPara-sailingPier FishingSailingSwimmingWind Surfing
Themes
FamilySports ActivitiesTourist Attractions
Location
Beach AccessWater View
Outdoor
Garden or BackyardPatio or BalconyBalconyPatio/Deck
Family
Room Darkening Shades
Website Categories
WaterfrontPrivate PoolTimes Square AreaShort Walk to BeachLive and UpdatedShort Stays
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

This date is not available for check-in.
The closest check-in date is February 11.Location
5.0
Stayed September 2026
5/5
"This was our second year staying at the same house and we felt right at home. We look forward to booking next year!"
Allison
Customer Relations Representative
Stayed August 2026
5/5
"Incredible place and views !! Excellent location"
Allison
Customer Relations Representative
Stayed August 2026
5/5
"Amazing location Thank you for great experience"
Allison
Customer Relations Representative
Stayed July 2026
5/5
"Beautiful family friendly rental with a fantastic pool and dock. My boys spent our entire stay swimming and fishing. Plenty of room and perfect for family vacations"
Allison
Customer Relations Representative
Stayed July 2026
5/5
"The house was beautiful! The views were amazing! You can sit out and watch the boats go by, hang out in the pool or walk to the beach . It was so relaxing. The home was one of the better stocked kitchens. The only thing to note is the twin beds are more like a day bed with a trundle. Would recommend! You won’t be disappointed."
Allison
Customer Relations Representative
Stayed June 2026
5/5
"Will definitely book again !!!!"
Allison
Customer Relations Representative
Stayed May 2026
5/5
"Exceptional - Great location,pool was awesome, views were amazing!"
Allison
Customer Relations Representative
Stayed April 2026
5/5
"Excellent location, beautiful home"
Allison
Customer Relations Representative
Stayed April 2026
5/5
"Great location and space for our family of 5!"
Allison
Customer Relations Representative
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
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
Stayed January 2026
5/5
"To say that it was one of the best vacation
experiences is an understatement. It was the best. Million dollar views, beautiful in and out."
Allison
Customer Relations Representative
Stayed January 2026
5/5
"To say that it was on the greatest vacation experiences ever is an understatement. This is a rare gem located in the heart of the beautiful bay community. Beautiful in and out, outdoor swimming pool, private dock. Stunning views through balconies and picture windows. Will go back in the heartbeat."
Allison
Customer Relations Representative
Stayed October 2025
5/5
"Loved the house and it was just perfect. The view was amazing. Couldn't ask for a better location and home. "
Allison
Customer Relations Representative
Stayed October 2025
5/5
"Loved the view and house. Location was just perfect."
Stayed August 2025
5/5
"We loved our visit to Fort Meyers. Dock Holiday was fantastic - stunning views, excellent amenities and right in the center of it all while still being quiet and relaxing."
Allison
Customer Relations Representative
Stayed August 2025
4/5
"Our family of 5 (10, 7, and 7 year old) had a wonderful week at Dock Holiday. The pool was a big hit. It was deeper than I expected. The younger kids needed life jackets but that was easy to take care of. We appreciated the beach wagon for our days at the beach. The house was a nice size for our family. All 3 bedrooms are on the 2nd floor, which was ideal for us. The views from the deck were beautiful. Host was responsive to needs."
Allison
Customer Relations Representative
Stayed August 2025
4/5
"Wir hatten einen großartigen Aufenthalt in dem Haus. Es ist riesig und bietet tolle Ausblicke, egal ob vom Balkon, von der Terrasse, vom Steg oder sogar direkt aus den Zimmern. Überall hat man einen traumhaften Blick aufs Wasser, was für uns ein absolutes Highlight war. Auch die Lage ist gut: sehr zentral und trotzdem ruhig, wenige Gehminuten zum Strand. Der Pool war sauber, lediglich der Boden wirkte schon etwas verfärbt und dunkler als auf den Fotos, was den ersten Eindruck leicht getrübt hat. Das Haus selbst ist sehr groß und sehr schön von außen, allerdings insgesamt schon etwas in die Jahre gekommen. Teppichböden, Küche, Bäder und Möbel entsprechen nicht mehr zeitgemäß, was bei der Ankunft auffällt, uns aber nicht stark gestört hat, da man viel Zeit draußen verbringt. Die Kommunikation mit der Vermietungsagentur gut und unkompliziert. Insgesamt tolles Haus mit einzigartiger Lage und traumhaftem Ausblick – mit etwas Modernisierung wäre es absolut perfekt."
Allison
Customer Relations Representative
Stayed June 2025
5/5
"We absolutely loved our stay and hope to return next year!"
Stayed June 2025
5/5
"We really enjoyed our time in Dock Holiday."
Allison
Customer Relations Representative
Stayed May 2025
5/5
"Amazing house, location and beautiful views. If we are ever by in the area we would book again. We stay in a beach house every summer, this one is the best one yet! A+++++"
Allison
Customer Relations Representative
Stayed May 2025
5/5
"The house was perfect for our family of 6 adults. The pool and outside area's are just beautiful. We saw dolphins swimming by the dock, lizards sunning themselves on the patio and all kinds of various birds. It was a great place to call home for a week."
Stayed April 2025
5/5
"very nice house, calm and really chilling to stay at !!"
Allison
Customer Relations Representative
Stayed April 2025
5/5
"Tolles Haus mit sehr guter Infrastruktur und eigenem Pool. Alles etwas in die Jahre gekommen, trotzdem absolut top und zu einem sehr guten Preis / Leistungsverhältnis. Wir würden wieder kommen :)"
Allison
Customer Relations Representative
Stayed April 2025
5/5
"We loved staying here! The location was convenient, it was a close walk to the beach and restaurants. The views were amazing and even spotted dolphins off of the dock."
Stayed March 2025
5/5
"Wonderful home - can't wait to stay there again!"
Allison
Customer Relations Representative
Stayed March 2025
5/5
"Beautiful home in a wonderful location! Great for families."
Allison
Customer Relations Representative
Stayed March 2025
5/5
"Beautiful house in a perfect location. Great vacation home for families. Pool was heated and perfect for the kids. Dolphins swam right up to the dock several times which the kids loved!"
Stayed February 2025
5/5
"Fantastic home and location. Some extra thoughts: The carpet upstairs is looking quite tired and stained. The master bedroom screen door on deck was and is off its runners, so never went out. Also no chair there to sit on. Pool had not been cleaned and pool cleaner had not shown on Wednesday afternoon yet. I called and you all were great at responding and getting them there the next am. Looked much better after he left. Corners could still use a scrub, but yuck at bottom mostly removed. Thanks. Also did let you know that dish water has a small leak around bottom seal. We controlled with a towel. No pot holder/hot pads, so used towels. Thanks also for supplying beach towels! It said they were not included and we were glad to see them and use around pool area. Cushions on covered patio off of living room will need replacing soon. As a previous rental owner, just thought I would give some extra feedback.
Would like to book two weeks in a row for next year."
Allison
Customer Relations Representative
Stayed January 2025
5/5
"Nice place. Has been updated since the Hurricane of 2022, but has a few things that need to be finished up yet."
Stayed January 2025
5/5
"Great!"
Stayed December 2024
5/5
"Me and my family absolutely loved staying at this property! Such a great location, walking distance to a lot of shops and restaurants. The view is so beautiful! We enjoyed sitting outside on the patio and on the dock. The pool was perfect and warm! Will definitely stay again!"
Stayed October 2024
5/5
"The view was breathtaking. Everyone is working hard to restore the island. So please show your support and stay at this beautiful home. It was easy access off the island. There are places to eat and enjoy cocktails on the island."
Stayed September 2024
5/5
"Everything was beautiful and the stay was great! Very clean, the views were amazing every morning! Pool was awesome! 10/10 reccommend!"
Stayed August 2024
5/5
"The house was very nice. Our family loved looking at the bay in the mornings and evenings. We saw dolphins multiple times over our week visit. The pool was very nice and the house was clean."
Allison
Customer Relations Representative
Stayed August 2024
5/5
"Beautiful place and cozy home. Even with hurricane debby passing thru we were still able to sit on the balcony’s and enjoy the views. Nice and open living room area and spacious dining room. I highly recommended this place for any family getaway."
Allison
Customer Relations Representative
Stayed August 2024
5/5
"Loved the home"
Stayed July 2024
5/5
"Beautiful home. Very spacious with an amazing view, short walk to the beach. Attention to detail from the landscaping to the large private driveway."
Allison
Customer Relations Representative
Stayed June 2024
5/5
"Beautiful location. The area is still being rebuilt from the hurricane but a great place to go for tranquility."
Stayed May 2024
5/5
"Beautiful place to relax and unwind. Everything was a breeze, and we all loved our vacation together time. Very professional, polite, and accommodating people to deal with! Loved Dock Holiday!"
Stayed March 2024
5/5
"Only comment is we only had 3 beach towels. Would have been nice to have 4. (One for each person staying)"
Stayed December 2023
5/5
"Great affordable spot."
Allison
Customer Relations Representative
Stayed November 2023
4/5
"Great location. Overall house was clean and had everything we needed. The dock at "Dock Holiday" was blocked off and un-usable, this was disappointing."
Allison
Customer Relations Representative
Stayed November 2023
5/5
"A beautiful place to stay, stocked with everything we could possibly need."
Stayed November 2023
5/5
"X"
Stayed November 2023
5/5
"6 of us went on a no-kid moms trip and the house was fantastic! We lounged by the pool and saw dolphins and string rays in the bay. There are 3 iguana's living in the rocks next door and we named them Terry, Theresa, and Tammy. The landscaping was beautiful. We all were very comfortable with the sleeping arrangements and there was wine glasses (wine fridge), pans, everything we needed. The couch is a pull-out. I also did not realize there is a bonus room in the garage with a futon and looked like AC and a full bath! This house could be great for 2-3 families. I also loved walking to time square and mojoes daily."
Stayed September 2023
5/5
"Awesome location. Will be back for sure."
Stayed August 2023
5/5
"Really nice place to stay, great location, and the pool was amazing."
Stayed July 2023
4/5
"The location is absolutely amazing! We were able to walk to the beach every morning to catch the sunrise and watched the sunset from the balcony and dining room every night. The pool needed maintenance. We called to have the pool serviced a couple of times. Kathy was extremely responsive and got the pool serviced each time very timely. The pool still had debris/rocks on the bottom after both cleanings and servicing and cut my son’s foot. Ten months post Hurricane Ian and a lot of rebuilding of the area and community continues. The boat ramp and deck still needs to be repaired. Overall we enjoyed the house and would stay again."
Allison
Customer Relations Representative
Rose J.
5/5 Stayed June 2022
"We loved it"
Roger
5/5 Stayed January 2022
"Great place and quiet location 5 mins from beach."
Lorraine
5/5 Stayed July 2021
"The so many plus to this property, deck, view and pool. If you want a clean comfortable house this is for you.
"
Stayed April 2021
5/5
"Spring break - Great location for family spring break! Dolphins greeted us near the dock on our last day!"
Allison
Customer Relations Representative
Karla Caplinger
5/5 Stayed April 2020
"Great location for family spring break! Dolphins greeted us near the dock on our last day!"
Dennis Schoening
5/5 Stayed March 2020
"Was very nice"
Mark Gessner
5/5 Stayed November 2019
""
Keith Barker
5/5 Stayed November 2019
"Like I said earlier it was a great property and we wanted to rent it in 2020."
Joe Yarzabal
4.5/5 Stayed November 2019
"Dock Holiday is an incredible property. The small quirks encountered along the way were surpassed by the location, views and pool area. Of course, the kitchen made things very comfortable."
Debbie McCartney
4.5/5 Stayed November 2019
"Loved the house and pool"
Michele Stork
4/5 Stayed November 2019
""
Wallace Duvall
5/5 Stayed June 2019
"Excellent property. Good communication from staff before and during stay. Excellent experience. Thank you!"
Jill Shay
3.5/5 Stayed June 2019
"We had a great vacation. Dock Holiday is a property that you never have to leave. The views are spectacular and the property had something for everyone....fishing, swimming, boating, sunbathing, swimming, and grilling. You’ll never have to leave! "
Jennifer Hurt
5/5 Stayed June 2019
"My family loved staying at the Dock Holiday rental. The house had amazing views of the waterway / bay from the kitchen and the living room, and you could enjoy the views from two of the bedrooms and the pool / dock area as well. It was nice and quiet on the canal side of the island, yet the walk to the beach was an easy 5 minutes. There was ample living space for the seven of us, and the house came with every appliance that you might need. Also, there were plenty of beach towels and bath towels, and many pool toys and beach toys for the kids to use. Overall, I would recommend the Dock Holiday house to anyone with a large family who is looking to relax and unwind by the water. "
Adjust dates according to the promotion description and the discount will be applied to the total.
Stay Four, Save More
Stay four, Save more. Save 12% off with the code SAVE12 when you book 4+ nights. Stay Dates: January 4th- January 31,2027 Book by: October 1, 2026.
1 Promotions available









