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Sugarloaf Key Hotels with Outdoor or Indoor Pools

Hilton Garden Inn The Keys Collection in Key West 3850 North Roosevelt Blvd., Key West, FL 33040 ~12.76 miles west of Sugarloaf Key
  • Pool in hotel: Outdoor pool
  • Mid-scale Resort property
From$129
Very Good 4.0 /5Review Score Call
Fairfield Inn & Suites Key West at the Keys Collection 3852 North Roosevelt, Key West, FL 33040 ~12.77 miles west of Sugarloaf Key
  • Pool in hotel: One pool
  • 3-star Resort property
From$75
Very Good 4.5 /5Reviews Call
The Gates Hotel Key West in Key West 3824 North Roosevelt Blvd., Key West, FL 33040 ~12.82 miles west of Sugarloaf Key
  • Has swimming pool: 2 Outdoor Pools and Pool Bar
  • 4 star Oceanfront property
From$129
Very Good 4.0 /5Reviews Call
24 North Hotel 3820 North Roosevelt Blvd., Key West, FL 33040 ~12.86 miles west of Sugarloaf Key
  • We have a pool
  • Midscale Resort property
From$109
Very Good 4.0 /5Reviews Call
Doubletree by Hilton Key West : 3990 South Roosevelt Blvd. 3990 South Roosevelt Blvd., Key West, FL 33040 ~12.93 miles west of Sugarloaf Key
  • Pool in hotel: 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
  • Midscale Resort hotel
From$156
Very Good 4.0 /5Review Score Call
Key West Bayside Inn & Suites : 3444 North Roosevelt Blvd. 3444 North Roosevelt Blvd., Key West, FL 33040 ~13.13 miles west of Sugarloaf Key
  • Pool available: 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%
  • 2-star Oceanfront property
The Inn at 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.
  • Midscale Oceanfront property
From$199
Very Good 4.0 /5Guest Reviews Call
Parrot Key Waterfront Hotel & Resort : 2801 North Roosevelt Blvd. 2801 North Roosevelt Blvd., Key West, FL 33040 ~14.02 miles west of Sugarloaf Key
  • Has swimming pool: 4 sparkling outdoor pools
  • 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%
  • Four star Resort hotel
From$169
Very Good 4.5 /5Reviews Call
Fairfield Inn & Siutes Key West in Key West 2400 North Rooselvelt Blvd., Key West, FL 33040 ~14.32 miles west of Sugarloaf Key
  • Pool available: A 72 gallon outdoor pool, conveniently located in front of our Tiki bar. Relax poolside on our comfortable lounge chairs, nestled between spectacular palm trees.
  • Outdoor pool and bar was awesome
  • Great pool
  • Excellent pool
  • Pool area is amazing
  • Pool and grounds were beautiful
  • Clean pool area
  • Clean pool, said 100%
  • Great poolside breakfast
  • Affordable Suburban hotel
From$319
Very Good 4.0 /5Read Reviews Call
Sheraton Suites Key West 2001 South Roosevelt Blvd., Key West, FL 33040 ~14.35 miles west of Sugarloaf Key
  • Pool details: 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 /5Hotel Reviews Call
Banana Bay Resort in Key West 2319 North Roosevelt Blvd., Key West, FL 33040 ~14.39 miles west of Sugarloaf Key
  • Has swimming pool: Pool on site, Topless optional
  • Pool is good
  • Great pool
  • Adorable pool setting
  • Nice pool area and hot tub
  • Great view of the pool
  • Midscale Beach property
Casa Marina a Waldorf Astoria Resort in Key West 1500 Reynolds St., Key West, FL 33040 ~15.53 miles west of Sugarloaf Key
  • Our hotel comes with 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 5 star Oceanfront hotel
From$209
Very Good 4.0 /5Hotel Reviews Call
The Reach Resort The Waldorf Astoria Collection - Key West 1435 Simonton St., Key West, FL 33040 ~15.76 miles west of Sugarloaf Key
  • Has a pool!
  • Good and friendly pool/beach service
  • Excellent location, private beach, pool
  • Pool is good
  • Great pool
  • Excellent pool area
  • Loved pool, beach and front staff
  • Pool in need of cleaning
  • Dirty pool, said 75%
  • Good pool/beach service
  • Lovely pool/beach service, according to 85%
  • Pool bar needs better service
  • High-end Oceanfront hotel
From$149
Very Good 4.0 /5Latest Reviews Call
Southernmost Beach Resort in Key West 508 South St. Key West, Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Pool details: 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 hotel
From$179
Very Good 4.5 /5Recent Reviews Call
The Paradise Inn 819 Simonton St., Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Pool in hotel
  • Clean pool area
  • Excellent pool
  • Great pool
  • Beautiful swimming pool
  • Plenty of pool towels
  • Pool area was amazing
  • Clean pool, said 90%
  • Midscale Downtown hotel
From$149
Very Good 4.5 /5Guest Reviews Call
Lighthouse Court Resort 902 Whitehead St., Key West, FL 33040 ~16.05 miles west of Sugarloaf Key
  • Has swimming 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
  • Three Star Downtown property
From$145
Very Good 4.0 /5Read Reviews Call
Crowne Plaza La Concha : 430 Duval St. 430 Duval St., Key West, FL 33040 ~16.06 miles west of Sugarloaf Key
  • Pool details: 7am-10pm
  • Pool/beach service is ok
  • About half of guests thought the pool/beach service was ok
  • Four-star Resort hotel
Pier House Resort & Spa : 1 Duval St. 1 Duval St., Key West, FL 33040 ~16.09 miles west of Sugarloaf Key
  • Has swimming pool
  • Good pool/beach service
  • Lovely pool/beach service, according to 82%
  • 4-star Beach property
From$239
Very Good 4.5 /5Review Score Call
Ocean Key Resort & Spa Zero Duval St., Key West, FL 33040 ~16.17 miles west of Sugarloaf Key
  • Has swimming pool
  • High-end Resort property
From$279
Very Good 4.5 /5Guest Reviews Call
The Westin Key West Resort & Marina in 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%
  • 4-star Resort property
From$229
Very Good 4.0 /5Review Score Call
Hyatt Key West Resort & Spa - Key West
+1-888-305-3366
601 Front St., Key West, FL 33040 ~16.28 miles west of Sugarloaf Key
  • Pool in hotel
  • 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 /5Read Reviews Call
Hyatt Place Marathon / Florida Keys : 1996 Overseas Highway 1996 Overseas Highway, Marathon, FL 33050 ~29.35 miles east of Sugarloaf Key
  • Includes a pool: Hyatt Place Pool Hours 6am-10pmOutdoorLighthouse Grill Pool Hours 6am-10pmOutdoor
  • Mid-scale Oceanfront property
From$139
Very Good 4.5 /5Review Score Call
Courtyard Marathon 2146 Overseas Highway, Marathon, FL 33050 ~29.42 miles east of Sugarloaf Key
  • Pool in hotel: Beautiful infinity pool located just at the waters edge.The pool has a heater and chiller and is 25,000 gallons.
  • Four star Resort property
Banana Bay Resort & Marina 4590 Overseas Highway, Marathon, FL 33050 ~30.64 miles east of Sugarloaf Key
  • Has swimming pool: 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%
  • Midscale Rural hotel
Sombrero Resort & Marina 19 Sombrero Blvd., Marathon, FL 33050 ~30.81 miles east of Sugarloaf Key
  • With a pool!
  • Mid-scale Resort property
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