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Sugarloaf Key Hotels with Outdoor or Indoor Pools

Oceans Edge Key West Resort Hotel & Marina in Key West 5950 Peninsular Ave., Key West, FL 33040 ~11.55 miles west of Sugarloaf Key
  • Pool in hotel: There are 6 pools, 3 closest to the bar/restaurant remain open until 9:00 PM. Poolside food/beverage service available.
  • High-end Oceanfront property
From$121
Very Good 4.5 /5Read Reviews CallBookMore Details
The Perry Hotel Key West - Key West 7001 Shrimp Rd., Key West, FL 33040 ~12.04 miles west of Sugarloaf Key
  • Pool details: Outdoor waterfront pool, open daily from 7am - 9pm.
  • High-end Oceanfront property
From$139
Very Good 4.5 /5Reviews CallBookMore Details
Hilton Garden Inn 3850 North Roosevelt Blvd., Key West, FL 33040 ~12.74 miles west of Sugarloaf Key
  • Pool details: Outdoor pool
  • Three Star Resort property
From$125
Very Good 4.0 /5Reviews CallBookMore Details
Fairfield Inn & Suites Key West at the Keys Collection 3852 North Roosevelt Blvd., Key West, FL 33040 ~12.74 miles west of Sugarloaf Key
  • Pool available: One pool
  • Midscale Resort hotel
From$129
Very Good 4.0 /5Latest Reviews CallBookMore Details
The Gates Hotel Key West 3824 North Roosevelt Blvd., Key West, FL 33040 ~12.80 miles west of Sugarloaf Key
  • Pool details: 2 Outdoor Pools and Pool Bar
  • High-end Oceanfront hotel
From$119
Very Good 4.0 /5Reviews CallBookMore Details
24 North Hotel 3820 North Roosevelt Blvd., Key West, FL 33040 ~12.84 miles west of Sugarloaf Key
  • Includes a pool: Outdoor
  • Four-star Resort hotel
From$109
Very Good 4.0 /5Hotel Reviews CallBookMore Details
Doubletree by Hilton Key West - Key West 3990 South Roosevelt Blvd., Key West, FL 33040 ~12.91 miles west of Sugarloaf Key
  • Includes a pool: Outdoor pool open from 7:30am - 11pm, daily
  • Great pool
  • Good pool
  • Pool was amazing, perfect
  • Great Pool area and outdoor bar
  • Beautiful grounds and pool area
  • Moderately clean pool area
  • About half of guests thought the pool was clean
  • Mid-scale Resort property
From$159
Very Good 4.0 /5Recent Reviews CallBookMore Details
Best Western Key Ambassador Resort Inn 3755 South Roosevelt Blvd., Key West, FL 33040 ~12.95 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • Three Star Oceanfront hotel
From$199
Very Good 4.0 /5Read Reviews CallBookMore Details
Havana Cabana Key West 3420 North Roosevelt Blvd., Key West, FL 33040 ~13.22 miles west of Sugarloaf Key
  • Pool available: We have the largest freshwater pool in Key West. It is open from 10AM - 11PM. The pool is heated.
  • Great pool
  • Pool area is amazing
  • Pool is good
  • Pool was amazing
  • Pool in need of cleaning
  • Dirty pool, said 58%
  • 3 star Oceanfront hotel
Parrot Key Waterfront Hotel & Resort 2801 North Roosevelt Blvd., Key West, FL 33040 ~13.99 miles west of Sugarloaf Key
  • Pool in hotel: 4 sparkling outdoor pools surrounded by maintained garden and tropical ambiance
  • Good pool/beach service
  • Beautiful grounds and pools
  • Great pool
  • Pool is good
  • 4 pools were separate but cozy
  • Chairs by the pool are wonderful
  • Clean pool area
  • Clean pool, said 90%
  • Pool staff was fabulous
  • Lovely pool/beach service, according to 88%
  • Expensive Resort property
From$169
Very Good 4.5 /5Review Score CallBookMore Details
Sheraton Suites Key West - Key West 2001 South Roosevelt Blvd., Key West, FL 33040 ~14.33 miles west of Sugarloaf Key
  • Has swimming pool: Outdoor lagoon style pool with cascading waterfall. Whirlpool also onsite.
  • 4-star Resort property
From$211
Very Good 4.0 /5Reviews CallBookMore Details
Banana Bay Resort & Marina : 2319 North Roosevelt Blvd. 2319 North Roosevelt Blvd., Key West, FL 33040 ~14.36 miles west of Sugarloaf Key
  • Has swimming pool: Pool on site, Topless optional
  • 3 star Beach property
Best Western Hibiscus Motel in Key West 1313 Simonton St., Key West, FL 33040 ~15.76 miles west of Sugarloaf Key
  • With a pool!
  • Mid-scale hotel
The Marker Waterfront Resort in Key West 200 William St., Key West, FL 33040 ~15.83 miles west of Sugarloaf Key
  • Pool in hotel: The Marker Waterfront Resort features 3 salt-water pools that are open 9am - 10pm daily. The serenity pool is for adults 21 years of age and older and is for those looking for a tranquil environment. Enjoy water aerobics in the main pools on Saturday mornings as well as Snuba on Tuesdays at 1030am for beginner Scuba Divers.
  • Four star Oceanfront property
From$155
Very Good 4.5 /5Reviews CallBookMore Details
Southernmost Beach Resort : 508 South St. Key West 508 South St. Key West, Key West, FL 33040 ~15.83 miles west of Sugarloaf Key
  • Has swimming pool: 3 pools; 1 pool adults only and 2 family friendly pools.
  • Pool is good
  • Great pool
  • Several pools and bars on site
  • Tranquility pool was very relaxing
  • Really enjoyed the pools and beach area
  • Clean pool area
  • Clean pool, said 100%
  • Four-star Beach property
From$185
Very Good 4.5 /5Read Reviews CallBookMore Details
Lighthouse Court Resort 902 Whitehead St., Key West, FL 33040 ~16.02 miles west of Sugarloaf Key
  • Has swimming pool: Heated outdoor pool. Hours: Dawn to Dusk.
  • Beautiful grounds and excellent pool
  • Pool is good
  • Great pool
  • Refreshing saltwater pool
  • Nice swimming pool
  • Pool bar was open
  • Moderately clean pool area
  • Approx. half of guests thought the pool was clean
  • 3-star Downtown hotel
From$169
Very Good 4.0 /5Latest Reviews CallBookMore Details
Crowne Plaza La Concha 430 Duval St., Key West, FL 33040 ~16.03 miles west of Sugarloaf Key
  • Includes a pool: 7am - Dusk
  • Pool/beach service is ok
  • About half of guests thought the pool/beach service was ok
  • Four star Resort property
From$199
Very Good 4.0 /5Recent Reviews CallBookMore Details
Ocean Key Resort & Spa - Key West Zero Duval St., Key West, FL 33040 ~16.14 miles west of Sugarloaf Key
  • Has a pool!
  • Expensive Resort property
From$289
Very Good 4.5 /5Read Reviews CallBookMore Details
Margaritaville Key West Resort & Marina 245 Front St., Key West, FL 33040 ~16.18 miles west of Sugarloaf Key
  • With a pool!
  • Four star Resort property
From$165
Very Good 4.0 /5Latest Reviews CallBookMore Details
Hyatt Key West Resort & Spa 601 Front St., Key West, FL 33040 ~16.25 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • Pool/beach service is ok
  • Most guests thought the pool/beach service was ok
  • Happy hour at pool bar was fantastic
  • Pool is mediocre
  • Ordinary pool
  • Complimentary pool towels
  • Pool chairs were old so
  • Luxury Five Star Oceanfront property
From$234
Very Good 4.5 /5Review Score CallBookMore Details
The Weatherstation Inn in Key West 57 Front St., Key West, FL 33040 ~16.26 miles west of Sugarloaf Key
  • Pool available: Outdoor Swimming Pool
  • Economical Downtown property
Hyatt Place Marathon / Florida Keys 1996 Overseas Highway, Marathon, FL 33050 ~29.32 miles east of Sugarloaf Key
  • Includes a pool: Hyatt Place Pool Hours 6am-10pmOutdoorLighthouse Grill Pool Hours 6am-10pmOutdoor
  • Three Star Oceanfront hotel
From$126
Very Good 4.5 /5Read Reviews CallBookMore Details
Courtyard Marathon 2146 Overseas Highway, Marathon, FL 33050 ~29.39 miles east of Sugarloaf Key
  • Pool available: Beautiful infinity pool located just at the waters edge.The pool has a heater and chiller and is 25,000 gallons.
  • 3 star Resort hotel
From$109
Very Good 4.5 /5Recent Reviews CallBookMore Details
Skipjack Resort Suites & Marina 19 Sombrero Blvd., Marathon, FL 33050 ~30.77 miles east of Sugarloaf Key
  • Has swimming pool: Open from 7:00am to 10:00pm Large heated pool 8 ft' deep
  • 3-star Resort property
From$139
Very Good 4.0 /5Guest Reviews CallBookMore Details
Coconut Cay Resort & Marina - Marathon 7196 Overseas Highway, Marathon, FL 33050 ~32.01 miles east of Sugarloaf Key
  • Has swimming pool: 24 hours
  • 2 star Resort property
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