Stock Island Hotels with Outdoor or Indoor Pools

Parrot Key Hotel & Villas 2801 North Roosevelt Blvd., Key West, FL 33040 Call ~0.34 miles southwest of Stock Island
  • Includes a pool: Five acres of tropical gardens surround Parrot Key Hotel & Villas, with beautiful paths meandering through colorful foliage. Four glimmering pools are nestled among their own private sculpture gardens setting the perfect scene for your tropical island experience. Grab a lounge chair and step outside your room. In the Key West sculpture gardens surrounding our pools, work includes the fantastical, larger-than-life stainless steel work of John Martini, a longtime Key West resident with his studio located in the Bahama Village neighborhood. Step through one of our rustic wooden doors from around the globe and serenity will greet you on the other side. Each of our pools is hidden away in its own oasis, surrounded by lush palms and island fauna to create an immediate sense of seclusion and privacy. We offer an exclusive adult only pool and 3 other pools for families to enjoy. Pool hours are Sunrise to Sunset daily with the exception of the pool nearest The Grove Restaurant and Bar which is open until 10 PM.
  • 4-star Resort hotel
From$360 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Havana Cabana at Key West : 3420 North Roosevelt Blvd. 3420 North Roosevelt Blvd., Key West, FL 33040 Call ~0.55 miles east of Stock Island
  • Pool details: We have the largest freshwater pool in Key West. It is open from 10AM - 11PM. The pool is heated.
  • 3-star Oceanfront hotel
From$262 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites Key West 2400 North Roosevelt Blvd., Key West, FL 33040 Call ~0.63 miles southwest of Stock Island
  • 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.
  • Mid-scale Suburban property
From$166 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Key West at the Keys Collectio 3852 North Roosevelt Blvd., Key West, FL 33040 Call ~0.64 miles southwest of Stock Island
  • Pool details: 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.
  • Midscale Suburban hotel
From$96 total
Average 3.0 /5 Review Score Call BookMore Details
Blue Flamingo Key West (Former 24north) in Key West 3820 B North Roosevelt Blvd., Key West, FL 33040 Call ~0.98 miles east of Stock Island
  • Includes a pool: Swimming Pool (07:00-22:00, outdoor) Number of pools (2) Pool sun loungers Pool umbrellas Hot tub/jacuzzi (nearby)
  • Four-star Resort property
From$270 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Gates Hotel Key West Newly Renovated in Key West 3820 a North Roosevelt Blvd., Key West, FL 33040 Call ~1.01 miles east of Stock Island
  • Pool in hotel: 2 Outdoor Pools and Pool Bar
  • Expensive Oceanfront property
From$210 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Key West / The Keys Collection in Key West 3850 North Roosevelt Blvd., Key West, FL 33040 Call ~1.10 miles east of Stock Island
  • Pool available: 4 outdoor swimming pools, each with their own adjacent pool bar
  • Midscale Resort property
From$238 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Doubletree Resort by Hilton Hotel Grand Key Key West - Key West 3990 South Roosevelt Blvd., Key West, FL 33040 Call ~1.36 miles east of Stock Island
  • Pool available: Outdoor pool open from 8:00am - 8pm, daily
  • 3 star Resort hotel
From$154 total
Very Good 4.0 /5 Reviews Call BookMore Details
The Perry Hotel & Marina Key West 7001 Shrimp Rd., Key West, FL 33040 Call ~1.97 miles east of Stock Island
  • Includes a pool: Two waterfront pools, one is open daily from 7am-9pm, the other from 11am-8pm.
  • 4 star Oceanfront hotel
From$130 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Ella's Cottages Key West Historic Inns 811 Simonton St., Key West, FL 33040 Call ~2.12 miles southwest of Stock Island
  • Includes a pool: Outdoor dipping pool in the courtyard is open from dawn to dusk. 8am-10pm
  • 2-star Downtown hotel
From$154 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Southernmost Beach Resort & Guesthouses 1319 Duval St., Key West, FL 33040 Call ~2.21 miles southwest of Stock Island
  • Pool details: 3 pools; 1 pool adults only and 2 family friendly pools.
  • Affordable Beach property
From$238 total
Average 3.0 /5 Reviews Call BookMore Details
La Concha Key West 430 Duval St., Key West, FL 33040 Call ~2.28 miles west of Stock Island
  • Includes a pool: 10am-Sunset
  • Four-star Resort hotel
From$300 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Lighthouse Hotel 902 Whitehead St., Key West, FL 33040 Call ~2.32 miles southwest of Stock Island
  • Includes a pool: Heated outdoor pool. Hours: Dawn to Dusk.
  • 3-star Downtown hotel
From$96 total
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Hilton Key West Resort & Marina : 5950 Peninsular Ave. 5950 Peninsular Ave., Key West, FL 33040 Call ~2.62 miles east of Stock Island
  • Pool available: There are 6 pools, 3 closest to the bar/restaurant remain open until 9:00 PM. Poolside food/beverage service available.
  • Expensive Oceanfront property
From$150 total
Very Good 4.5 /5 Read Reviews Call BookMore Details
Lunara Bay in Key West 12 Andrea Ln, Key West, FL 33040 Call ~2.64 miles east of Stock Island
  • Pool details: Each individual home has it's own private pool
  • Luxurious Five Star Oceanfront property
From$240 total
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Beachside Resort & Residences 3841 North Roosevelt Blvd., Key West, FL 33040 Call ~1.16 miles east of Stock Island
  • Our hotel comes with a pool
  • High-end Oceanfront property
From$214 total
Very Good 4.0 /5 Reviews Call BookMore Details
Hyatt Vacation Club at Windward Pointe in Key West 3675 South Roosevelt Blvd., Key West, FL 33040 Call ~1.65 miles southeast of Stock Island
  • Has a pool!
  • 4 star Oceanfront property
From$150 total
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Hampton Inn Key West FL - Key West 3755 South Roosevelt Blvd., Key West, FL 33040 Call ~1.72 miles southeast of Stock Island
  • Has swimming pool
  • Midscale Oceanfront property
From$96 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Casa Marina Key West, Curio Collection by Hilton 1500 Reynolds St., Key West, FL 33040 Call ~1.99 miles southwest of Stock Island
  • We have a pool ready for use
  • Luxury Five Star Oceanfront hotel
From$274 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Paradise Inn Key West Adults Only 819 Simonton St., Key West, FL 33040 Call ~2.12 miles southwest of Stock Island
  • Includes a swimming pool
  • 3-star Downtown property
From$178 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Hibiscus Motel - Key West 1313 Simonton St., Key West, FL 33040 Call ~2.13 miles southwest of Stock Island
  • Our hotel comes with a pool
  • Low Cost hotel
From$72 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Ocean Key Resort & Spa Zero Duval St., Key West, FL 33040 Call ~2.38 miles west of Stock Island
  • With a pool!
  • Expensive Resort hotel
From$338 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Isla Bella Beach Resort & Spa in Marathon 1 Knights Key Blvd., Marathon, FL 33050 Call ~41.80 miles east of Stock Island
  • Has swimming pool: 5 Outdoor pools, chilled in the summer and heated in the winter. Pool bar offering refreshing drinks and light fare. Shoreline is almost a mile long, lounge chairs, umbrellas and cold drinks at the beach bar.
  • High-end Oceanfront hotel
From$154 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Faro Blanco Resort Marathon Florida Keys Curio by Hilton : 1996 Overseas Highway 1996 Overseas Highway, Marathon, FL 33050 Call ~42.87 miles east of Stock Island
  • Has swimming pool: Faro Blanco Resort Marathon Florida Keys, Curio by Hilton Pool Hours 6am-10pm Outdoor Lighthouse Grill Pool Hours 6am-10pm Outdoor
  • Expensive Oceanfront hotel
From$150 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott Faro Blanco Resort : 2146 Overseas Highway 2146 Overseas Highway, Marathon, FL 33050 Call ~42.97 miles east of Stock Island
  • Includes a pool: Two onsite waterfront pools including an infinity pool edge overlooking the beautifully clear ocean. Two additional pools available at adjacent Faro Blanco Resort.
  • 3 star Resort property
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Banana Bay Resort & Marina 4590 Overseas Highway, Marathon, FL 33050 Call ~44.20 miles east of Stock Island
  • Includes a pool: 8AM-10PM We have one of the biggest outdoor pools in Marathon.
  • 3 star Rural hotel
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
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