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Sugarloaf Key Hotels with Outdoor or Indoor Pools

Hilton Garden Inn 3850 North Roosevelt Blvd., Key West, FL 33040 ~12.76 miles west of Sugarloaf Key
  • Pool available: Outdoor pool
  • Three Star Resort hotel
From$139
Very Good 4.0 /5Recent Reviews Call
Fairfield Inn & Suites Key West at the Keys Collection - Key West 3852 North Roosevelt, Key West, FL 33040 ~12.77 miles west of Sugarloaf Key
  • Pool available: One pool
  • Affordable Resort hotel
From$115
Very Good 4.5 /5Read Reviews Call
The Gates Hotel Key West in Key West 3824 North Roosevelt Blvd., Key West, FL 33040 ~12.82 miles west of Sugarloaf Key
  • Pool in hotel: 2 Outdoor Pools and Pool Bar
  • 4 star Oceanfront hotel
From$129
Very Good 4.0 /5Review Score Call
24 North Hotel 3820 North Roosevelt Blvd., Key West, FL 33040 ~12.85 miles west of Sugarloaf Key
  • With a pool!
  • Affordable Resort property
From$119
Very Good 4.0 /5Hotel Reviews Call
Doubletree by Hilton Key West - Key West 3990 South Roosevelt Blvd., Key West, FL 33040 ~12.93 miles west of Sugarloaf Key
  • Has swimming 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
  • 3 star Resort property
From$169
Very Good 4.0 /5Read Reviews Call
Best Western Key Ambassador 3755 South Roosevelt Blvd., Key West, FL 33040 ~13.01 miles west of Sugarloaf Key
  • Has a pool!
  • Mid-scale Oceanfront hotel
From$219
Very Good 4.0 /5Latest Reviews Call
Key West Bayside Inn & Suites : 3444 North Roosevelt Blvd. 3444 North Roosevelt Blvd., Key West, FL 33040 Website ~13.13 miles west of Sugarloaf Key
  • Includes a pool: We have an outdoor pool, open until 9pm.
  • Great pool
  • Nice pool area
  • Good pool
  • Pool which was quite nice
  • Clean pool area
  • Clean pool, said 93%
  • Cheap Oceanfront property
The Inn at Key West - Key West 3420 North Roosevelt Blvd., Key West, FL 33040 ~13.22 miles west of Sugarloaf Key
  • Includes a pool: We have the largest freshwater pool in Key West. It is open from 10AM - 11PM. The pool is heated.
  • 3-star Oceanfront hotel
From$149
Very Good 4.0 /5Reviews Call
Parrot Key Waterfront Hotel & Resort - Key West 2801 North Roosevelt Blvd., Key West, FL 33040 ~14.02 miles west of Sugarloaf Key
  • Pool details: 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%
  • High-end Resort property
From$120
Very Good 4.5 /5Reviews Call
Sheraton Suites Key West in Key West 2001 South Roosevelt Blvd., Key West, FL 33040 ~14.35 miles west of Sugarloaf Key
  • Pool in hotel: Outdoor lagoon style pool with cascading waterfall. Whirlpool also onsite.
  • Pool was amazing
  • Pool is good
  • Great pool
  • Excellent pool
  • Pool was perfect
  • Moderately clean pool area
  • Approx. half of guests thought the pool was clean
  • Four-star Resort property
From$175
Very Good 4.0 /5Recent Reviews Call
Banana Bay Resort 2319 North Roosevelt Blvd., Key West, FL 33040 ~14.39 miles west of Sugarloaf Key
  • Pool details: Pool on site, Topless optional
  • Pool is good
  • Great pool
  • Adorable pool setting
  • Nice pool area and hot tub
  • Great view of the pool
  • Mid-scale Beach property
Casa Marina a Waldorf Astoria Resort - Key West 1500 Reynolds St., Key West, FL 33040 ~15.53 miles west of Sugarloaf Key
  • Has a pool!
  • Good and friendly pool/beach service
  • Good pool
  • Great pool
  • Pool is beautiful and serene
  • We loved the pool- and beach
  • Pools and grounds are beautiful
  • Pool in need of cleaning
  • Dirty pool, said 62%
  • Good pool/beach service
  • Lovely pool/beach service, according to 93%
  • Pool bar needs better service
  • Luxury Five Star Oceanfront property
From$209
Very Good 4.0 /5Latest Reviews Call
Key Lime Inn in Key West 725 Truman Ave., Key West, FL 33040 ~15.69 miles west of Sugarloaf Key
  • We have a pool ready for use
  • Excellent pool
  • Great pool
  • Outdoor pool a bonus
  • Lovely pool area
  • Breakfast by the pool a delight
  • Clean pool area
  • Clean pool, said 100%
  • Affordable Downtown hotel
From$129
Very Good 4.5 /5Review Score Call
The Reach Resort & Beach Club in Key West 1435 Simonton St., Key West, FL 33040 ~15.74 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • 4-star Oceanfront property
Southernmost Beach Resort 508 South St. Key West, Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Includes a 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%
  • 4-star Beach property
From$219
Very Good 4.5 /5Review Score Call
The Paradise Inn in Key West 819 Simonton St., Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • Clean pool area
  • Excellent pool
  • Great pool
  • Beautiful swimming pool
  • Plenty of pool towels
  • Pool area was amazing
  • Clean pool, said 90%
  • Midscale Downtown property
From$149
Very Good 4.5 /5Reviews Call
Lighthouse Court Resort - Key West 902 Whitehead St., Key West, FL 33040 ~16.05 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • 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$145
Very Good 4.0 /5Latest Reviews Call
Crowne Plaza La Concha 430 Duval St., Key West, FL 33040 ~16.06 miles west of Sugarloaf Key
  • Has swimming pool: 7am-10pm
  • Pool/beach service is ok
  • About half of guests thought the pool/beach service was ok
  • 4 star Resort property
From$229
Very Good 4.0 /5Guest Reviews Call
Pier House Resort & Spa 1 Duval St., Key West, FL 33040 ~16.09 miles west of Sugarloaf Key
  • Has a pool!
  • Good pool/beach service
  • Lovely pool/beach service, according to 82%
  • High-end Beach hotel
From$239
Very Good 4.5 /5Reviews Call
Ocean Key Resort & Spa Zero Duval St., Key West, FL 33040 ~16.17 miles west of Sugarloaf Key
  • Includes a swimming pool
  • Four star Resort property
From$279
Very Good 4.5 /5Guest Reviews Call
Margaritaville Key West 245 Front St., Key West, FL 33040 ~16.20 miles west of Sugarloaf Key
  • Includes a pool
  • Great pool
  • Good pool/beach service
  • Lovely pool/beach service, according to 86%
  • High-end Resort property
From$262
Very Good 4.0 /5Review Score Call
Hyatt Key West Resort & Spa : 601 Front St. 601 Front St., Key West, FL 33040 ~16.28 miles west of Sugarloaf Key
  • Has swimming 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
  • Luxurious Five Star Oceanfront property
From$259
Very Good 4.5 /5Review Score Call
Hyatt Place Marathon / Florida Keys : 1996 Overseas Highway 1996 Overseas Highway, Marathon, FL 33050 ~29.35 miles east of Sugarloaf Key
  • Pool in hotel: Hyatt Place Pool Hours 6am-10pmOutdoorLighthouse Grill Pool Hours 6am-10pmOutdoor
  • Three Star Oceanfront property
From$139
Very Good 4.5 /5Recent Reviews Call
Courtyard Marathon in Marathon 2146 Overseas Highway, Marathon, FL 33050 ~29.42 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.
  • Three Star Resort property
Banana Bay Resort & Marina 4590 Overseas Highway, Marathon, FL 33050 ~30.64 miles east of Sugarloaf Key
  • Pool details: 8AM-10PMWe have one of the biggest outdoor pools in Marathon.
  • Pool is mediocre
  • Ordinary pool
  • Tiki bar by the pool was not available
  • Pool area needs work
  • Nice pool and hot tub
  • Pool in need of cleaning
  • Dirty pool, said 78%
  • Mid-scale Rural property
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