Why it made this week's list
The most interesting booking window right now is November into early December. Key West moves out of its wettest period, with November averaging about 81°F by day and just over 2 inches of rain; December averages about 78°F. That creates a useful middle ground between hot, wetter early fall and the busier winter holiday season.
Families should be careful with October 16–25, 2026, when Fantasy Fest takes over much of Old Town. Some events are family-friendly, but the festival overall is a major adult-oriented street-party period and can change the feel of downtown considerably.
The Marker is particularly worth checking because its Old Town location lets you enjoy Key West without paying for a rental car every day—and that matters when hotel parking alone is $44 plus tax nightly.
Why families may like it
This works especially well for families who like exploring together rather than spending five straight days inside a resort. The Historic Seaport is immediately outside the hotel, Duval Street is only a few blocks away, and Mallory Square is roughly a 10-minute walk.
Back at The Marker, three pools give you an easy afternoon break after sightseeing. Families of four can consider two-queen rooms of up to 400 square feet, with a private terrace; larger one- and two-bedroom suites are also available.
The tradeoff: there is no beach directly at the hotel and no verified kids club or organized children’s program. This is better for children who enjoy boats, wildlife, history and exploring than families expecting waterslides and supervised activities. Key West nightlife can also become noticeably more adult-oriented later in the evening, particularly around parts of Duval Street.
Hotel overview
The Marker occupies a quiet pocket beside the Historic Seaport, only three blocks from Duval Street. Inside the property, two acres of tropical landscaping and three pools make it surprisingly easy to forget you are staying in the middle of Old Town. One pool is reserved for adults, leaving the others available for families.
Rooms are unusually spacious by Old Town standards. Every room category listed by the hotel includes a private balcony; two-queen rooms sleep up to four, while Serenity and Marker Residence suites provide considerably more room for larger or multigenerational groups.
Starboard serves breakfast and other meals poolside, although breakfast is not normally included in the standard rate. There is no verified kids club, teen program or full-service spa onsite. The resort fee currently includes access to the beach and spa at sister property Southernmost Beach Resort, but families should confirm exactly what that access includes before relying on it.
The biggest drawback is cost beyond the room rate: the current resort fee is $56 plus tax per night, and onsite parking is $44 plus tax nightly.
Best for
Families with school-age children: Great for kids interested in boats, snorkeling, butterflies, forts and unusual history. Less ideal if a kids club or water park is essential.
Families with teenagers: Older kids can appreciate watersports, biking, sunset cruises and exploring Old Town. Some stretches of Duval become more adult-focused late at night.
Multigenerational families: Larger suites, walkable sightseeing and the ability to split time between pools and attractions work well. Confirm accessibility needs carefully when choosing room type.
Families who explore beyond the hotel: Probably the strongest fit. You can walk to restaurants, harbor excursions and many Old Town attractions.
Couples adding a family-free trip: The adults-only pool, harbor location and nightlife make The Marker work equally well without children.
Key West, FL
Key West feels less like a conventional Florida beach town and more like a small Caribbean-influenced historic city that happens to sit at the end of U.S. Highway 1. Colorful wooden homes, roaming roosters, banyan trees, fishing boats and old brick streets create much of its character.
From The Marker, begin with the Historic Seaport, where fishing boats, schooners, restaurants and excursion operators line the harbor. Continue toward Mallory Square for the nightly sunset gathering, then explore the historic streets around Duval and Whitehead. The southern end of town contains the Southernmost Point, Key West Butterfly & Nature Conservatory and quieter residential blocks.
Families should also leave downtown for Fort Zachary Taylor Historic State Park, combining a Civil War-era fort with one of Key West’s best swimming beaches. Water shoes are useful because the shoreline is coral rather than soft sand.
A car is unnecessary for most days at The Marker. The hotel is about an 11-minute drive from Key West International Airport, while Duval and Mallory Square can be reached on foot.
The biggest mistake would be treating Key West purely as a resort destination. The island itself is the attraction.
Things to do with children
Mallory Square Sunset Celebration — all ages | 1–2 hours. Arrive before sunset for performers, boats and the evening crowd. Roughly a 10-minute walk from The Marker.
Fort Zachary Taylor — ages 5+ | half day. Tour the Civil War fort, swim, snorkel and picnic. Water shoes are strongly recommended on the coral beach.
Butterfly & Nature Conservatory — especially ages 3–12 | 1 hour. Walk among butterflies, tropical birds and flamingos. Children 3 and under are currently free; open daily.
Hemingway Home — ages 7+ | 1–1.5 hours. The six-toed cats often make the literary history much more interesting to children. Open daily 9–5.
Historic Seaport — all ages | 1–2 hours. An easy, inexpensive wander directly by the hotel with boats, shops and waterfront snacks.
Snorkel or dolphin cruise — school-age children/teens | 3–4 hours. The Marker partners with Fury for watersports; book ahead and check sea conditions.
Conch Train/trolley tour — younger children | 1–2 hours. Useful on a hot or tired day when everyone wants sightseeing without more walking.
Mel Fisher Maritime Museum — ages 7+ | 1–2 hours. Shipwreck treasure gives older children a tangible way into Key West’s maritime history.
Sample family itinerary
Day 1: Settle Into Key West
Morning: Travel day.
Afternoon: Check in after 4 p.m.; unpack and swim.
Evening: Walk the Historic Seaport and have an easy waterfront dinner.
Family note: Skip ambitious sightseeing tonight.
Day 2: Old Town
Morning: Hemingway Home and Whitehead Street.
Afternoon: Pool and rest at The Marker.
Evening: Mallory Square sunset.
Day 3: Beach & Fort
Morning: Fort Zachary Taylor fort tour.
Afternoon: Beach, snorkeling and picnic.
Evening: Casual dinner near the harbor.
Family note: Bring water shoes.
Day 4: Slow Island Day
Morning: Butterfly Conservatory.
Afternoon: Long pool break.
Evening: Key lime pie and an early Old Town walk.
Day 5: On the Water
Morning/Afternoon: Family snorkeling, dolphin-watching or sailing excursion.
Evening: Final sunset and favorite restaurant.
Family note: Keep a museum backup if seas are rough.
Day 6: Departure
Morning: Breakfast, short harbor stroll and 11 a.m. checkout.
Best time to visit
For many families, November through April offers the easiest weather. Key West’s dry season runs roughly December–April. November is a transition month, making late November and early December especially interesting before peak holiday travel.
Normal temperatures remain warm: October averages about 86°F/77°F, November 81°F/72°F and December 78°F/68°F. Average coastal water temperature is approximately 84°F in October, 78°F in November and 75°F in December.
Summer and early fall bring more heat, humidity and thunderstorms. June through October accounts for roughly 65% of annual rainfall, and hurricane risk must be considered during tropical-storm season.
Best overall: November–April
Best value: Often September–early December outside major events/holidays
Best weather: December–April
Best for fewer crowds: November or early December
Period to approach carefully: August–October for storms; Oct. 16–25, 2026 for family trips because of Fantasy Fest.
Family travel tips
Fly into Key West if the fare works. EYW is roughly an 11-minute drive from the hotel. Driving from Miami can be scenic, but it turns arrival and departure into substantial travel days.
Think twice before renting a car. The Marker is exceptionally walkable for Key West, while onsite parking currently costs $44 plus tax per night. A short taxi or rideshare may be cheaper overall.
Pack water shoes. Fort Zachary Taylor has a coral shoreline, not the powder-soft sand families may expect from Florida beaches.
Choose your room strategically. Two-queen rooms sleep four; larger families should price one- or two-bedroom suites rather than assuming a standard room can accommodate everyone.
Build in pool time. Heat and walking add up quickly in Old Town. A 2–3 hour afternoon break often makes evening sightseeing far more enjoyable with children.
Important things to know before booking
Resort fee: The Marker currently charges $56 plus tax per room, per night. On a five-night trip, that is $280 before tax beyond the advertised room rate.
Parking: Covered onsite parking is currently $44 plus tax nightly, limited to one vehicle per room.
No onsite beach: This is a harbor/Old Town hotel, not a beachfront resort. Resort-fee benefits currently include beach and spa access at sister property Southernmost Beach Resort; confirm current access details before booking.
Cancellation: Standard policy currently calls for cancellation at least 10 days before arrival; Fantasy Fest, Christmas and New Year reservations require 30 days. Specials and advance-purchase rates may have stricter rules.
Check-in: The registered guest must be at least 21. Check-in is 4 p.m.; checkout is 11 a.m.
Final thoughts
Key West is a strong choice for families who want their vacation to include more than just resort time. Staying at The Marker puts you close to the Historic Seaport, Old Town attractions, sunset celebrations, restaurants, and boat excursions, while still giving you a comfortable place to slow down by the pool between adventures.
This trip is especially appealing for families with school-age children or teenagers who enjoy exploring, wildlife, history, snorkeling, and being out on the water. It may be less ideal for families looking for a traditional beachfront resort with a kids club and activities scheduled throughout the day.
For a five-night stay, the best approach is to mix a few planned experiences with plenty of unscheduled time. Explore Key West in the mornings, cool off at the hotel in the afternoons, and head back out for dinner and sunset. That relaxed rhythm fits the island well—and is one of the reasons Key West can make such a memorable family trip.
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