Southwinds Motel – Key West Resort Review
Last updated: August 28, 2026
Choose Southwinds Motel if...
- You want the cheapest stay in Old Town with free parking included
- You want to be one block from both Duval Street and South Beach
- You want a lively on-site bar and two pools without resort prices
Skip Southwinds Motel if...
- You expect luxury finishes or modern decor — this is a basic motel
- You're a light sleeper — there's an active bar on-site
- You want spacious suites or resort-level amenities
AskTheKeys Traveler Match
How well does Southwinds Motel fit your trip?
Before you book — the one trade-off
Southwinds is a no-frills budget motel — you trade modern finishes and spacious rooms for an unbeatable price one block from Duval and South Beach.
AskTheKeys Decision SummarySouthwinds Motel is best for budget travelers who want a no-frills Old Town location one block from both Duval Street and the Atlantic Ocean, with free parking, two pools, and Key West's top-rated bar on-site. Not ideal for guests expecting luxury finishes, modern decor, or spacious rooms.
Southwinds Motel is a 58-room budget motel on Simonton Street in Old Town Key West with free parking, 2 outdoor pools, complimentary continental breakfast, free laundry, and the TripAdvisor #1-rated bar in Key West (Tipsy Rooster) on-site. One block from Duval Street and one block from the Atlantic Ocean, it delivers the best location-to-price ratio in Key West.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Budget travelers wanting the cheapest Old Town option
- Guests who value free parking in Old Town
- Bar enthusiasts (Tipsy Rooster, TripAdvisor #1 bar, on-site)
- Travelers wanting beach proximity at budget pricing
- Visitors who prioritize location over room quality
Not ideal for
- Guests expecting luxury or modern finishes
- Travelers wanting spacious rooms or suites
- Light sleepers (active bar on-site)
- Guests wanting resort-level amenities
Quick facts
| Address | 1321 Simonton Street, Key West, FL 33040 |
|---|---|
| Phone | +13052962829 |
| Check-in / Out | 3:00 PM / 11:00 AM |
| Parking | Free on-site |
| Pets | No |
| Beach access | Yes |
| Pool(s) | Yes |
| Spa | No |
| EV charging | No |
Location & nearby
Southwinds Motel is located in Old Town – South Duval / Simonton Corridor within Key West.
What's nearby
- Duval Street(0.1 mi, 1 min walk)
- Southernmost Point(0.1 mi, 2 min walk)
- South Beach(0.1 mi, 1 min walk)
- Key West Butterfly Conservatory(0.2 mi, 3 min walk)
- Ernest Hemingway Home & Museum(0.3 mi, 6 min walk)
- Key West Lighthouse(0.3 mi, 5 min walk)
- Mallory Square(0.8 mi, 16 min walk)
- Fort Zachary Taylor State Park(0.7 mi, 14 min walk)
Amenities overview
Property highlight features
- Free on-site parking
- 2 outdoor pools
- Complimentary continental breakfast
- Tipsy Rooster bar on-site (TripAdvisor #1 Key West bar)
- 1 block from Duval and 1 block from South Beach
Pricing positioning
Typical nightly pricing tends to fall in the $ range, depending on season and room type.
budget (seasonal)
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We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How Southwinds Motel Compares to Other Key West Resorts
Southwinds Motel vs Silver Palms Inn
- Southwinds Motel wins:budget motel near Southernmost Point with 2 pools and on-site bar
- Silver Palms Inn wins:modern boutique motel on Truman Ave with saltwater pool and free parking
Southwinds Motel vs Southernmost Beach Resort
- Southwinds Motel wins:budget motel one block from South Beach with free parking and top-rated on-site bar
- Southernmost Beach Resort wins:full-scale beachfront resort with tiki bar, multiple pools, and premium amenities at 3x the nightly rate
Southwinds Motel vs Eden House
- Southwinds Motel wins:budget motel with 2 pools and beach proximity at lowest Old Town price point
- Eden House wins:historic mid-range hotel with tropical garden pool and hammock courtyard on Fleming Street
FAQs
Is Southwinds Motel the cheapest option in Old Town Key West?
Southwinds is consistently among the lowest-priced stays in Old Town, with rates starting around $136 per night. Combined with free parking and breakfast, the effective daily cost is very competitive.
Does Southwinds Motel have free parking?
Yes. Free on-site parking is included, saving $30–$55 per night compared to most Old Town Key West hotels.
What is the Tipsy Rooster?
The Tipsy Rooster is a bar and liquor store on the Southwinds property, rated #1 bar in Key West on TripAdvisor. It serves handcrafted cocktails and hosts live music.
How close is Southwinds to the beach?
South Beach (Atlantic Ocean) is one block away. Southernmost Point is a 2-minute walk.
Is breakfast included at Southwinds?
Yes. A complimentary continental breakfast is included with every stay.
Are the rooms modern at Southwinds?
Rooms are clean and functional but basic. This is a traditional motel, not a boutique hotel. Guests should expect no-frills accommodations at budget pricing.
Is Southwinds good for families?
Yes. Two-queen-bed rooms accommodate families, free parking reduces costs, and the pools and beach proximity keep children entertained. Free cribs are available.
Does Southwinds charge a resort fee?
No. There is no resort fee. The rate includes parking, breakfast, Wi-Fi, laundry access, and pool use.