7 day itinerary? Traveling with small dog

Question

Driving down through Florida in February. Looking to stay 5-7 days in the keys. Have a small dog so sorting thru pet friendly hotels and even campgrounds if we have to. Thinking 3-4 days in Islamorada and 3 nights in KW. Maybe Marathon and/or Key Largo on way the way back. Looking for recommendations on where to stay, etc. would prefer less than $500 per night for hotel if possible. Bringing camping gear just in case there is tent camping available - and we can’t find reasonable accommodations. Is it unwise to just wing it - considering it’s busy season? Dislike having a hard itinerary

Answer

February is one of the busiest, most expensive months in the Florida Keys, so traveling with a small dog, wanting accommodations under $500 per night, and hoping to “wing it” can be challenging — but not impossible if you choose the right islands and stay flexible. Below is a very detailed breakdown of realistic expectations, best pet-friendly hotels, dog-friendly activities, and whether you should book ahead.

Overall guidance for February travel

February is peak season due to perfect weather, high tourism numbers, and many events. Pet-friendly rooms are fewer than standard rooms, so they book out earlier. Camping is available but also fills fast, especially in state parks like Bahia Honda. If you dislike strict itineraries, you can stay flexible with activities, but you should not wing it entirely for lodging — at least book your first few nights and Key West accommodations.

Suggested 7-day structure

Days 1–3: Islamorada (relaxed, dog-friendly, easy shoreline access)
Days 4–6: Key West (walkable, lots of dog-friendly patios)
Day 7: Key Largo or Marathon overnight on your way back north

Best pet-friendly lodging options (under $500/night in February)

Prices vary widely by exact dates, but the following places are known to have pet-friendly rooms at reasonable rates (by Keys standards) if you book early.

Islamorada:
- La Siesta Resort & Marina – Very dog-friendly, large rooms, quiet beachfront atmosphere, usually under $500 early in February.
- Hadley House Resort – Pet-friendly waterfront option with modern rooms and walkability.
- Pines & Palms Resort – Older-style cottages, charming, and many allow pets.
Key West:
- Kimpton Key West (multiple properties) – Among the most pet-friendly brands in KW; sometimes under $500 depending on dates and room types.
- Silver Palms Inn – Boutique, good location, often more affordable than big resorts.
- Southwinds Motel – Budget-friendly for Key West, pet rooms available, superb location near Duval but quiet.
Marathon:
- Isla Bella Beach Resort – Beautiful but can be pricey; occasionally dips around $450–$550.
- Captain Pip’s Marina & Hideaway – Dog-friendly, basic but clean, waterfront.
Key Largo:
- Baker’s Cay Resort – Stunning but often hits the upper end of your range.
- Hampton Inn Key Largo – Good value, pet-friendly, near John Pennekamp State Park.

Dog-friendly things to do in each area

Islamorada:
- Dog-friendly breweries like Florida Keys Brewing Co.
- Walks around the Morada Way Arts District.
- Robbie’s Marina (walk around, see tarpon — dogs allowed on docks).
Key West:
- Dog Beach and the nearby popular dog-friendly bar.
- Walk Duval Street (many patios allow dogs).
- Waterfront boardwalk around Mallory Square.
- Fort Zachary Taylor picnic areas (dogs allowed on trails, not on the main beach).
Marathon:
- Walk the Old Seven Mile Bridge to Pigeon Key (dogs allowed on leash).
- Sombrero Beach (dog-friendly areas depending on tides).
- Crane Point Hammock has some dog-friendly trails.
Key Largo:
- John Pennekamp State Park (dogs allowed on trails/campground, not beaches).
- Dagny Johnson Key Largo Hammock Preserve.

Camping options (if lodging becomes limited)

Tent camping in the Keys during February is popular and must be booked early unless you get a same-day cancellation. These campgrounds allow dogs:

Bahia Honda State Park (Big Pine Key) – Stunning; extremely competitive to book.
John Pennekamp Coral Reef State Park (Key Largo) – Convenient and pet-friendly.
Boyd’s Campground (Key West) – Private, well-run, fills up early in February.
Sunshine Key RV Resort (near Bahia Honda) – More availability than state parks.

Is it unwise to “wing it” in February?

For February in the Keys, the honest answer is: yes, it’s risky to wing it, especially with a dog. Even roadside motels run near full capacity. Pet-friendly rooms are more limited and sell out faster than standard rooms. If you show up without bookings, you could spend $700+ because only premium rooms remain — or find no availability at all in Key West for that night.

However, if you want flexibility, here is the best compromise:

Book Key West in advance — this is the hardest and riskiest place to wing it.
Book at least the first 2–3 nights in Islamorada or Key Largo.
Leave Marathon/Key Largo on the return leg flexible — these areas have more availability and more budget properties.
Keep 1–2 campgrounds reserved as a backup (or track daily cancellations).

Sample 7-day dog-friendly itinerary (flexible, realistic)

Day 1 – Arrive Key Largo: Explore Pennekamp trails, settle in.
Day 2–4 – Islamorada: Relax, breweries, art district, beaches at sunrise/sunset.
Day 5–7 – Key West: Duval Street walks, sunset celebrations, Dog Beach, Fort Zachary trails.
Optional – Day 7 alternative: Marathon overnight (Sombrero Beach + Old Seven Mile Bridge).

Final advice

Your plan — Islamorada + Key West + possibly Marathon/Key Largo — is perfect for a February drive with a small dog. Just avoid going in blind for accommodations. Book the most competitive stops (Key West and first few nights) and keep the rest open for enjoyment. This gives you enough structure to avoid stress but enough freedom to wander and enjoy the islands at your own pace.