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Sugarloaf Key Hotels with Outdoor or Indoor Pools

Hilton Garden Inn The Keys Collection 3850 North Roosevelt Blvd., Key West, FL 33040 ~12.76 miles west of Sugarloaf Key
  • Has swimming pool: Outdoor pool
  • Three Star Resort hotel
From$129
Very Good 4.0 /5Review Score Call
The Gates Hotel 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$159
Very Good 4.0 /5Guest Reviews Call
24 North Hotel 3820 North Roosevelt Blvd., Key West, FL 33040 ~12.86 miles west of Sugarloaf Key
  • Includes a pool
  • Mid-scale Resort property
From$109
Very Good 4.0 /5Reviews Call
Doubletree by Hilton Key West - Key West 3990 South Roosevelt Blvd., Key West, FL 33040 ~12.93 miles west of Sugarloaf Key
  • Pool available: Outdoor pool open from 7:30am - 11pm, daily
  • 3-star Resort hotel
From$156
Very Good 4.0 /5Recent Reviews Call
Best Western Key Ambassador 3755 South Roosevelt Blvd., Key West, FL 33040 ~13.01 miles west of Sugarloaf Key
  • We have a pool ready for use
  • 3-star Oceanfront property
From$219
Very Good 4.0 /5Review Score Call
Key West Bayside Inn & Suites 3444 North Roosevelt Blvd., Key West, FL 33040 ~13.13 miles west of Sugarloaf Key
  • Includes a pool: We have an outdoor pool, open until 9pm.
  • Low priced Oceanfront hotel
Inn at Key West 3420 North Roosevelt Blvd., Key West, FL 33040 ~13.25 miles west of Sugarloaf Key
  • Pool in hotel: We have the largest freshwater pool in Key West. It is open from 10AM - 11PM. The pool is heated.
  • Midscale Oceanfront hotel
From$119
Very Good 4.0 /5Review Score Call
Fairfield Inn & Siutes Key West : 2400 North Rooselvelt Blvd. 2400 North Rooselvelt Blvd., Key West, FL 33040 ~14.32 miles west of Sugarloaf Key
  • Includes a pool: 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.
  • Affordable Suburban property
From$319
Very Good 4.0 /5Review Score Call
Sheraton Suites Key West 2001 South Roosevelt Blvd., Key West, FL 33040 ~14.35 miles west of Sugarloaf Key
  • Has swimming pool: Outdoor lagoon style pool with cascading waterfall. Whirlpool also onsite.
  • Four star Resort property
From$175
Very Good 4.0 /5Review Score Call
Banana Bay Resort : 2319 North Roosevelt Blvd. 2319 North Roosevelt Blvd., Key West, FL 33040 ~14.39 miles west of Sugarloaf Key
  • Includes a pool: Pool on site, Topless optional
  • Midscale Beach property
From$171
Average 3.0 /5Reviews Call
Casa Marina a Waldorf Astoria Resort 1500 Reynolds St., Key West, FL 33040 ~15.53 miles west of Sugarloaf Key
  • With a pool!
  • Luxurious 5-star Oceanfront hotel
From$209
Very Good 4.0 /5Read Reviews Call
The Reach Resort The Waldorf Astoria Collection : 1435 Simonton St. 1435 Simonton St., Key West, FL 33040 ~15.76 miles west of Sugarloaf Key
  • With a pool!
  • Four star Oceanfront hotel
From$149
Very Good 4.0 /5Review Score Call
Southernmost Beach Resort in Key West 508 South St. Key West, Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Has swimming pool: 3 pools; 1 pool adults only and 2 family friendly pools.
  • 4-star Beach property
From$179
Very Good 4.5 /5Reviews Call
The Paradise Inn 819 Simonton St., Key West, FL 33040 ~15.86 miles west of Sugarloaf Key
  • Pool in hotel
  • Mid-scale Downtown hotel
From$149
Very Good 4.5 /5Latest Reviews Call
Lighthouse Court Resort 902 Whitehead St., Key West, FL 33040 ~16.05 miles west of Sugarloaf Key
  • Has a pool!
  • Three Star Downtown property
From$145
Very Good 4.0 /5Hotel Reviews Call
Crowne Plaza La Concha : 430 Duval St. 430 Duval St., Key West, FL 33040 ~16.06 miles west of Sugarloaf Key
  • Pool in hotel: 7am-10pm
  • Expensive Resort property
Pier House Resort & Spa - Key West 1 Duval St., Key West, FL 33040 ~16.09 miles west of Sugarloaf Key
  • Our hotel comes with a pool
  • Four-star Beach hotel
From$239
Very Good 4.5 /5Guest Reviews Call
Ocean Key Resort & Spa : Zero Duval St. Zero Duval St., Key West, FL 33040 ~16.17 miles west of Sugarloaf Key
  • With a pool!
  • High-end Resort hotel
From$279
Very Good 4.5 /5Recent Reviews Call
The Westin Key West Resort & Marina 245 Front St., Key West, FL 33040 ~16.20 miles west of Sugarloaf Key
  • Has a pool!
  • 4 star Resort hotel
From$229
Very Good 4.0 /5Read Reviews Call
Hyatt Key West Resort & Spa - Key West
+1-800-881-1523
601 Front St., Key West, FL 33040 ~16.28 miles west of Sugarloaf Key
  • Pool in hotel
  • Luxurious Five Star Oceanfront hotel
From$259
Very Good 4.5 /5Read Reviews Call
Hyatt Place Marathon / Florida Keys in Marathon 1996 Overseas Highway, Marathon, FL 33050 ~29.35 miles east of Sugarloaf Key
  • Has swimming pool: Hyatt Place Pool Hours 6am-10pmOutdoorLighthouse Grill Pool Hours 6am-10pmOutdoor
  • Three Star Oceanfront hotel
From$139
Very Good 4.5 /5Hotel Reviews Call
Banana Bay Resort & Marina : 4590 Overseas Highway 4590 Overseas Highway, Marathon, FL 33050 ~30.64 miles east of Sugarloaf Key
  • Includes a pool: 8AM-10PMWe have one of the biggest outdoor pools in Marathon.
  • Three Star Rural property
Sombrero Resort & Marina in Marathon 19 Sombrero Blvd., Marathon, FL 33050 ~30.81 miles east of Sugarloaf Key
  • We have a pool
  • 3 star Resort property
Coconut Cay Resort & Marina in Marathon
+1-800-997-5148
7196 Overseas Highway, Marathon, FL 33050 ~31.99 miles east of Sugarloaf Key
  • Pool in hotel: Open 24 hours outdoor, large sun deck with lounge chairs, picnic tables
  • 2-star Resort property
Siesta Motel in Marathon 7425 Overseas Highway, Marathon, FL 33050 ~32.15 miles east of Sugarloaf Key
  • Has swimming pool: 2 FREE RESORT POOLS FOR GUEST ACCESS NEARBY
  • 2 star Rural property
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