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Blue Flamingo Resort Key West Key West, Florida
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Hotel comparison guide

Blue Flamingo Resort Key West vs Winslow's Bungalows Key West Historic Inns

Blue Flamingo Resort Key West is a renovated, family-friendly 4-star resort on North Roosevelt Boulevard with two lively pools, poolside restaurants, and a shuttle to Old Town — a good read if you want a social, activity-focused stay near the airport. Winslow's Bungalows Key West Historic Inns is a 4-star collection of historic bungalow-style rooms in Old Town — read this if you prefer character, walkable access to Duval Street, and small-inn charm.

Updated · about 3.1 miles (5.0 km) apart

Resort pool and five-story Blue Flamingo Resort Key West facade with palm trees

Blue Flamingo Resort Key West

Family-friendly · 2 pools & social programming · Near EYW / shuttle to Old Town

Best for families and groups who want on-site entertainment, multiple pools, and an easy airport-adjacent base with shuttle access to Old Town.

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

Winslow's Bungalows Key West Historic Inns

Historic bungalows · Old Town / walkable to Duval · Multiple small pools

Best for travelers who want historic Old Town character, short walks to Duval Street, and a quieter inn-style stay with bungalow options.

Quick Verdict: Blue Flamingo Resort Key West vs Winslow's Bungalows Key West Historic Inns

When Blue Flamingo Resort Key West wins: choose Blue Flamingo if you want a livelier, family-friendly resort with scheduled evening entertainment, two main pools plus cabanas, on-site tiki dining and a resort-fee shuttle to Old Town.

When Winslow's Bungalows wins: pick Winslow's Bungalows if you want to stay in Old Town for easy walking access to Duval Street, museums, and beaches, and if you prefer boutique bungalow-style rooms and several small outdoor pools in a garden setting.

Bottom line: for activity, social programming, and a resort atmosphere near the airport, go with Blue Flamingo. For historic character, location inside Old Town, and walkability to Key West sights, go with Winslow's Bungalows.

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Blue Flamingo Resort Key West vs Winslow's Bungalows Key West Historic Inns – At a Glance

Side-by-side facts for Blue Flamingo Resort Key West and Winslow's Bungalows Key West Historic Inns
CategoryBlue Flamingo Resort Key WestWinslow's Bungalows Key West Historic Inns
Overall vibeResort, lively social programming, family-focusedHistoric-inn, low-rise bungalow charm, Old Town atmosphere
LocationNew Town / gateway area near Key West Intl. Airport; shuttle to Old TownOld Town, a short walk (about 5 minutes) from Duval Street and close to Key West beaches
SizeLarge resort with 245 roomsSmaller inn collection with 85 guestrooms
Ages / audienceAll ages; family-friendly with children’s play areaAll ages (not adults-only); historic-inn clientele
PoolsTwo outdoor pools plus hot tub and cabanas; Backyard Pool & Social Club programmingThree outdoor pools; poolside bar Bungalow Bar
Restaurants & barsRum Row (tiki food truck) and Toasted Coconut (poolside restaurant) plus on-site coffee shop and barsBungalow Bar (poolside) with American cuisine; continental breakfast available (fee)
Wellness / fitness24-hour fitness center; hot tub/jacuzzi on site (no named standalone spa published)Not published
Known forLively pool scene, evening entertainment, and event/wedding capacityHistoric bungalow setting and very walkable access to Old Town attractions
Parking & transportOn-site self-parking (surcharge); resort-fee shuttle to Old Town; ~1 mile to EYWSelf parking (surcharge) listed; close to Old Town walking routes; preferred airport EYW ~3.3 mi
Accessible featuresMultiple accessibility features noted (accessible paths, pool access, parking)Wheelchair accessible (may have limitations); wheelchair-accessible pool and registration desk

A Look Inside Blue Flamingo Resort Key West

Blue Flamingo Resort Key West: rooms & suitesRooms & suitesBlue Flamingo Resort Key West: pools & beachPools & beachBlue Flamingo Resort Key West: diningDiningBlue Flamingo Resort Key West: spa & wellnessSpa & wellness
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Location: New Town resort vs Old Town bungalows

Blue Flamingo Resort Key West – Location

Blue Flamingo sits in New Town at the island’s northern gateway, close to Key West International Airport with shuttle service into Old Town.

  • About 1 mile from Key West International Airport; resort-fee shuttle to Old Town included.
  • Near Smathers Beach and the Key West Tropical Forest & Botanical Garden.
  • Shuttle and free/paid local transport options make downtown accessible despite the distance.

Choose Blue Flamingo if you want quick airport access and don’t mind a short shuttle or drive into Old Town.

Winslow's Bungalows Key West Historic Inns – Location

Winslow's Bungalows is in Old Town, within an easy walk of Duval Street, museums, and nearby beaches.

  • Located at 725 Truman Avenue, roughly a 5-minute walk to Duval Street and close to several Old Town landmarks.
  • Good base for exploring museums, bars, and waterfront attractions on foot.
  • Less need for shuttles or car use when your plans stay inside Old Town.

Pick Winslow's for maximum walkability to Key West’s main Old Town sights and nightlife.

Rooms: resort suites & ocean views vs bungalow-style guestrooms

Blue Flamingo Resort Key West – Rooms

Blue Flamingo offers 245 rooms with pool, garden, or ocean views including suites and ocean-view studios.

  • Room types include Room, Room (Pool View), Room (Island View, High Floor), Room, Ocean View, Studio Suite, Ocean View, and 1‑Bedroom Suites.
  • Rooms designed for families and groups; resort lists specific bedding and larger suite footprints.
  • Free property-wide Wi‑Fi; some rooms offer ocean views and access to resort amenities.

Blue Flamingo is likely easier for families needing larger or connecting rooms and suite options.

Winslow's Bungalows Key West Historic Inns – Rooms

Winslow’s offers a variety of bungalow-style rooms and suites (85 guestrooms) with historic character.

  • Room types include Bungalow, Bungalow King, Classic King, Premier King with Patio or Balcony, Treehouse Suite, and multiple accessible options.
  • Rooms emphasize Old Town character — options include patios, balconies, and some unique suites like a Treehouse King Suite.
  • Complimentary Wi‑Fi and in-room conveniences such as safes and LED TVs are standard.

Winslow’s is better if you want a smaller, characterful room type selection in Old Town rather than a typical resort layout.

Dining & drinks: poolside tiki & casual island fare vs small-inn bar dining

Blue Flamingo Resort Key West – Dining & drinks

Blue Flamingo centres dining around poolside venues and casual island-inspired food and tiki cocktails.

  • Rum Row is a tiki Caribbean bar/food truck with cocktails and poolside bites; hours extend later on weekends.
  • Toasted Coconut serves breakfast and daytime meals poolside; the property also has an on-site Starbucks and bars.
  • Dining ties into pool programming and evening entertainment (happy hour windows listed).

Blue Flamingo focuses on casual, family-friendly poolside dining and tiki cocktails across multiple venues.

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

Winslow’s offers smaller-scale dining focused on a poolside bar and continental breakfast service.

  • Bungalow Bar serves American cuisine in a garden/poolside setting.
  • Continental breakfast is available daily for a fee rather than included in room rate.
  • Fewer on-site venues than a resort — Old Town offers many nearby dining options within walking distance.

Choose Winslow’s if you plan to eat out in Old Town and prefer a small-inn poolside bar rather than resort dining options.

Pools & the signature amenity: social pool scene vs garden bungalow pools

Blue Flamingo Resort Key West – Pools & the signature amenity

Blue Flamingo’s signature amenity is its Backyard Pool & Social Club — two pools with cabanas and active programming.

  • Two main pools, cabanas available for rent, lawn games, karaoke and evening entertainment around pool areas.
  • Pool access and poolside programming are part of the resort-fee inclusions.
  • Hot tub/jacuzzi available; pool hours published and year-round access noted.

Blue Flamingo is for travelers who want programmed pool activities and a lively social scene on site.

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

Winslow’s sets itself apart with multiple smaller outdoor pools set among bungalow gardens.

  • The property lists three outdoor pools and a poolside bar (Bungalow Bar) for relaxed pooltime.
  • Pool settings are more intimate and distributed across the bungalow grounds than a single resort pool deck.
  • Poolside service and garden views are part of the Old Town bungalow experience.

Winslow’s is better if you prefer quieter, garden-style pool areas close to Old Town rather than a single active pool club.

Wellness & nightlife: fitness & programmed entertainment vs neighborhood nightlife

Blue Flamingo Resort Key West – Wellness & nightlife

Blue Flamingo combines a 24-hour fitness center with regular on-site evening entertainment.

  • 24-hour fitness center available for guests.
  • Resort programming includes live music, karaoke, and evening events tied to pool areas.
  • No named full-service spa is published; a hot tub/jacuzzi is available.

Blue Flamingo fits guests who want on-site entertainment and a fitness facility without leaving the property.

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

Winslow’s places you inside Old Town nightlife and dining rather than focusing on in-house evening programming.

  • Winslow’s listing emphasizes proximity to Duval Street nightlife and Old Town attractions.
  • On-site nightlife is limited to poolside bar service; the area’s bars and venues are within walking distance.
  • Spa or dedicated fitness facility not published in the supplier listing.

Pick Winslow’s to be close to Old Town nightlife and walk off property for evenings out.

Who Wins? Best Pick by Travel Style

Best for families & groups
Framed coastal artwork and wooden paddle wall display at Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

Blue Flamingo — two pools, kids’ play area, arcade/game room, evening programming, and larger room/suite inventory.

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

Winslow's Bungalows Key West Historic Inns

Winslow's Bungalows — short walk to Duval Street, museums, and nearby beaches; bungalow setting keeps you in the heart of Old Town.

Best for a resort pool scene
Decorative shelving with model sailboat and framed photos at Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

Blue Flamingo — Backyard Pool & Social Club with active programming, cabanas, tiki bar, and live entertainment.

Best for historic character
Winslow's Bungalows Key West Historic Inns, Key West, Florida

Winslow's Bungalows Key West Historic Inns

Winslow's Bungalows — historic bungalow-style rooms and garden setting that emphasize Old Town character.

Frequently asked questions

Blue Flamingo Resort Key West vs Winslow's Bungalows Key West Historic Inns: FAQs

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Which property is closer to Key West International Airport?

Blue Flamingo is closer to Key West Intl. Airport — about 1 mile from EYW; Winslow’s is in Old Town, roughly a 3–3.5 mile drive from the airport.

Which is better if I want to walk to Duval Street every night?

Winslow's Bungalows is the better choice for walkability to Duval Street and Old Town attractions; Blue Flamingo provides a shuttle but is not within easy walking distance.

Are the pools very different between the two?

Yes. Blue Flamingo has two main resort pools with dedicated programming and cabanas; Winslow’s has multiple (three) smaller outdoor pools set among bungalow grounds for a quieter pool experience.

Do either property’s room rates include breakfast?

Blue Flamingo’s standard room rates do not include breakfast (breakfast is optional, paid on-site). Winslow’s lists continental breakfast as available for a fee.

More Blue Flamingo Resort Key West Comparison Guides

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Resort pool deck with loungers, umbrellas and palm trees at Blue Flamingo Resort Key West
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