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Casa Marina Key West Key West, Florida
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Hotel comparison guide

Casa Marina Key West vs Winslow's Bungalows Key West Historic Inns

Casa Marina Key West is a historic, full-service 4-star oceanfront resort with private beach, on-site spa, multiple restaurants and large event spaces; read this if you want a resort with beachfront pools and a full program of services. Winslow's Bungalows Key West Historic Inns is a 4-star, bungalow-style property in Old Town Key West—read this if you prefer smaller, residential-style accommodations within walking distance of Duval Street.

Updated · about 0.8 km apart

Front façade and palm-lined entrance of Casa Marina Key West at dusk

Casa Marina Key West

Oceanfront · Full-service resort · Spa & events

Best for travelers who want a full-service beachfront resort with multiple pools, a spa, and large event/wedding facilities.

Winslow's Bungalows Key West Historic Inns, Key West, Florida

Winslow's Bungalows Key West Historic Inns

Boutique bungalows · Old Town location · Poolside bar

Best for travelers who want compact bungalow-style rooms in the heart of Old Town within easy walking distance of Duval Street.

Quick Verdict: Casa Marina Key West vs Winslow's Bungalows Key West Historic Inns

When Casa Marina Key West wins: choose Casa Marina if you want private beach access, two oceanfront pools (including an adults-only pool), Spa al Maré, larger rooms and suites, and resort services geared to families, couples and events.

When Winslow's Bungalows wins: choose Winslow's if you prefer a smaller, historic bungalow experience, being centrally located (about a 5-minute walk to Duval Street) and staying in a property with multiple small outdoor pools and a poolside bar.

Bottom line: Casa Marina is the resort option for beach- and amenity-focused stays and events; Winslow's is a lower-scale, Old Town option for guests prioritizing proximity to downtown Key West and a bungalow atmosphere.

Casa Marina Key West vs Winslow's Bungalows Key West Historic Inns – At a Glance

Side-by-side facts for Casa Marina Key West and Winslow's Bungalows Key West Historic Inns
CategoryCasa Marina Key WestWinslow's Bungalows Key West Historic Inns
Overall vibeLarge historic oceanfront resort with resort services, event spaces and spa.Small historic bungalow-style inn collection with a residential, Old Town feel.
LocationOceanfront on private beach (Higgs Beach area), under a mile from Duval Street.Central Old Town address (725 Truman Avenue), about a 5-minute walk to Duval Street.
Size311 rooms and suites across multiple buildings.85 guestrooms.
Age policy / audienceFamily-friendly; children welcome; adults-only pool available.Not adults-only; welcomes guests of all sexual orientations and gender identities.
Pools & beachTwo refurbished oceanfront pools (one adults-only, one family) plus private beach access (~1,100 ft private shoreline).Three outdoor pools and a poolside bar; not a beachfront property.
Restaurants & barsMultiple outlets including Dorada (oceanfront Baja‑Med) and The Canary Room cocktail bar, plus Flagler's Restaurant and Morrison's Market.Bungalow Bar (poolside) and one bar/lounge; continental breakfast available for a surcharge.
Spa & wellnessSpa al Maré with massages, facials, beachfront cabanas, fitness center and scheduled yoga.Not published
Known forLargest private beach in Key West for a hotel, large event and wedding venues, full resort services.Historic bungalow accommodations in a central Old Town location close to Duval Street.
Onsite parkingSelf- and valet parking are available (fees apply).Self parking (surcharge) available onsite.
Wi‑Fi & practicalsResort fee applies; internet access included in the resort charge for public areas; in-room access policies vary.Free WiFi; front desk with limited hours (7:00 AM–11:00 PM).

Location: Casa Marina vs Winslow's Bungalows

Casa Marina Key West – Location

Casa Marina sits directly on more than 1,100 feet of private Key West shoreline near Higgs Beach and within easy reach of Old Town.

  • Oceanfront address: 1500 Reynolds Street; private beach access and beach services.
  • Less than a mile from Duval Street and the Ernest Hemingway Home and Museum (walkable or short local ride).
  • Shuttle between Casa Marina and sister property The Reach is included in the resort charge.

Choose Casa Marina if you want direct ocean access and resort beach facilities.

Winslow's Bungalows Key West Historic Inns – Location

Winslow's Bungalows is in central Old Town at 725 Truman Avenue, placing you within a short walk of Duval Street and historic attractions.

  • Centrally located: about a 5-minute walk to Duval Street and roughly 10 minutes on foot to Florida Keys beaches.
  • Close to the Ernest Hemingway Home and Museum and Key West Lighthouse (0.4–0.6 km range).
  • Front-desk hours are limited; check-in details and policies require a photo ID and card for incidentals.

Choose Winslow's if you want to stay in Old Town within easy walking distance of bars, restaurants and galleries.

Rooms: space and style

Casa Marina Key West – Rooms

Casa Marina offers 311 rooms and suites in a mix of oceanfront, pool view and city-view layouts, including multi-room suites.

  • 22 room types including Oceanfront Suite with Balcony, 2 Bedroom Loft, Lilly Pulitzer Suites and accessible options.
  • Rooms range from standard city/pool views to larger oceanfront suites and lofts.
  • Accessible rooms and facilities are available; some modernized in a recent renovation.

Pick Casa Marina for more room types and larger suites suited to families, groups and events.

Winslow's Bungalows Key West Historic Inns – Rooms

Winslow's offers bungalow-style and classic rooms across 85 guestrooms with many named room types.

  • Room types include Bungalow, Bungalow King, Premier King with Patio or Balcony, Treehouse King Suite and King Suite with Soaking Tub.
  • Smaller property scale means more intimate, residential-feeling accommodations.
  • Complimentary WiFi, LED TVs and designer toiletries in private bathrooms.

Pick Winslow's for smaller, character rooms and bungalow layouts in an Old Town setting.

Dining & drinks: resort variety vs bungalow simplicity

Casa Marina Key West – Dining & drinks

Casa Marina has multiple dining outlets and bars including an oceanfront signature restaurant and a lobby cocktail bar.

  • Dorada: oceanfront Baja‑Med restaurant serving lunch and dinner (reservations recommended).
  • The Canary Room cocktail bar in the lobby (daily hours and happy hour) plus Flagler's Restaurant and Morrison's Market.
  • Private 'Toes in the Sand' chef-curated beachfront dining available by reservation.

Choose Casa Marina for more on-site dining variety and oceanfront meal options.

Winslow's Bungalows Key West Historic Inns – Dining & drinks

Winslow's focuses on a smaller food-and-drink footprint centered on poolside service.

  • Bungalow Bar: a poolside bar/lounge serving American cuisine and drinks with garden views.
  • Continental breakfast available for a surcharge (served 8:00 AM–10:00 AM).
  • On-site concierge can help with restaurant recommendations and reservations in Old Town.

Choose Winslow's if you plan to eat out in Old Town and want a simple on-site bar for casual meals and drinks.

Pools, beach & signature amenity

Casa Marina Key West – Pools, beach & signature amenity

Casa Marina centers on its private beach plus two refurbished oceanfront pools (adults-only and family-friendly).

  • Two oceanfront pools, one adults-only and one family pool (family pool max depth 4'6").
  • Beach services include chaises, umbrellas, cabanas and watersports launched from the beach.
  • Poolside cabana and daybed rentals with food and beverage service; pool concierge included in resort charge.

Choose Casa Marina if large beachfront and pool facilities matter to you.

Winslow's Bungalows Key West Historic Inns – Pools, beach & signature amenity

Winslow's provides a quieter bungalow-pool experience with multiple outdoor pools and a poolside bar.

  • Three outdoor pools and pool sun loungers with outdoor furniture.
  • Poolside Bungalow Bar serves light meals and drinks with garden views.
  • Not a beachfront property; beaches and public shorelines are a short walk away.

Choose Winslow's for a compact stay with multiple small pools and easy walking access to Old Town beaches.

Wellness & nightlife

Casa Marina Key West – Wellness & nightlife

Casa Marina offers a full spa program and a larger fitness center plus evening bars on property.

  • Spa al Maré open daily with massages, facials and beachfront cabana treatments; signature Ocean Breeze Massage available.
  • Large fitness center with Peloton bikes, free classes and paid premium classes; sunrise beach yoga scheduled.
  • Evening options include The Canary Room cocktail bar and beachside dining at Dorada.

Choose Casa Marina if you want a full spa and fitness program on-site plus resort evening dining.

Winslow's Bungalows Key West Historic Inns – Wellness & nightlife

Winslow's has limited on-site wellness details and is best used as a base for exploring Key West nightlife.

  • No spa information published in supplier listing.
  • Close to Key West nightlife and bars on Duval Street within a short walk.
  • Concierge and tours/tickets assistance available to book local experiences.

Choose Winslow's if you want front‑door access to Key West nightlife and will use off-site spas or fitness options.

Who Wins? Best Pick by Travel Style

Best for beach & resort amenities
Seating area with green sofas and fireplace in the Casa Marina Key West lobby

Casa Marina Key West

Casa Marina — private beach, two oceanfront pools, full spa and large event spaces.

Best for Old Town access
Winslow's Bungalows Key West Historic Inns, Key West, Florida

Winslow's Bungalows Key West Historic Inns

Winslow's Bungalows — central Truman Avenue location a short walk from Duval Street and historic sites.

Best for small-group or boutique stays
Winslow's Bungalows Key West Historic Inns, Key West, Florida

Winslow's Bungalows Key West Historic Inns

Winslow's Bungalows — bungalow-style rooms and a more residential, intimate setting.

Best for events and weddings
Wide view of the Casa Marina Key West lobby with columns, sofas and windows

Casa Marina Key West

Casa Marina — extensive indoor/outdoor event spaces and large wedding capacities, plus beachfront ceremony options.

Frequently asked questions

Casa Marina Key West vs Winslow's Bungalows Key West Historic Inns: FAQs

See all FAQs →
Which hotel is closer to Duval Street?

Winslow's Bungalows is closer—about a 5-minute walk to Duval Street; Casa Marina is under a mile and within walking or short local-ride distance.

Which property has a private beach?

Casa Marina has roughly 1,100 feet of private beach. Winslow's is not a beachfront property; beaches are within a short walk.

Is Winslow's adults-only?

No—Winslow's Bungalows is not published as adults-only; it welcomes a broad range of guests.

Which property is better for a spa-focused stay?

Casa Marina — Spa al Maré is on the property and offers a full menu of treatments; Winslow's does not publish an on-site spa.

Covered cabana seating with loungers facing the ocean at Casa Marina Key West.
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