The Best Cudjoe Key Hotels with Pools from $127 - Hotels with indoor pools in Cudjoe Key, FL

A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

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Our top choices for Cudjoe Key hotels with a pool

1. Parmer's Resort

Summerland Key

Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.

$142 nightly

Aug 30 - Aug 31

Total with taxes and fees

2. Sugar Loaf Lodge

Summerland Key

Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.

$119 nightly

Aug 16 - Aug 17

Total with taxes and fees

Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers

3. Looe Key Reef Resort

Summerland Key

Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.

$113 nightly

Aug 12 - Aug 13

Total with taxes and fees

10 outdoor pools, pool umbrellas, sun loungers

4. Atlantic View Luxury Villa with Pool

Summerland Key

Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days.

$1,075 nightly

Aug 11 - Aug 12

Total with taxes and fees

Outdoor pool, open 8:30 AM to 8:00 PM, sun loungers

5. Old Wooden Bridge Resort and Marina

Punta Brisa

Soak in tropical views at the outdoor pool, then paddle away from this waterfront cottage with an onsite marina and private dock.

$225 nightly

Sep 1 - Sep 2

Total with taxes and fees

6 outdoor pools, free cabanas, pool umbrellas

6. Hilton Key West Resort & Marina

Stock Island

Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.

$175 nightly

Aug 17 - Aug 18

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

7. Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

$148 nightly

Aug 30 - Aug 31

Total with taxes and fees

Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)

8. Hilton Garden Inn Key West / The Keys Collection

New Town

Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.

$126 nightly

Aug 20 - Aug 21

Total with taxes and fees

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Breakfast included

4 stars

Top Cudjoe Key Hotel Reviews

Ibis Bay Beach Resort

8/10 Good

"Property is old but clean …. Wasn’t thrilled that it was stated online that a shuttle was available at the site. There wasn’t a shuttle to get downtown ."

Parrot Key Hotel & Villas

10/10 Excellent

"We had a wonderful stay. Our balcony overlooks the ocean. We enjoyed the sunsets. House keeping was not good. They were short personal. We got our towels changed out everyday but no cleaning our room except for one day out of 5 days. The grounds was pretty and maintained. The restaurant was outside but nice. Chicken and roasters everywhere. The whole island was like that. The rooms were quiet and had ceiling fans in each room. I would stay here again. Parking was valet only."

Beachside Resort & Residences

8/10 Good

"The property was very nice but in need a daily maintenance: Lawn cleaned and mowed to keep up resort type appearance that it should. Probably should hose off the stairs and benches of chicken droppings, also to look resort worthy. All said and done, the room was exceptionally nice (ice maker didn't work) and the amenities were good - though some beach chairs were broken however it is noted, some of the tourist around the pool were nasty and there were kids jumping on those chairs. It is a good location, easy to go anywhere and the restaurant was very nice."

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"Really nice Hotel and pool. Really good bar and food by the pool. Only complaint was the 5 nights I was there house keeping never once came to refresh my room. Good thing i brought detergent and a washer and dryer was in the room. Everything was great but that would've made it spectacular."

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Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

1. Parmer's Resort

2. Sugar Loaf Lodge

3. Looe Key Reef Resort

4. Atlantic View Luxury Villa with Pool

5. Old Wooden Bridge Resort and Marina

6. Hilton Key West Resort & Marina

7. Hampton Inn Key West FL

8. Hilton Garden Inn Key West / The Keys Collection

9. Beachside Resort & Residences

10. DoubleTree Resort by Hilton Grand Key - Key West

Choose what matters most at hotels with a pool in Cudjoe Key

Top Cudjoe Key Hotel Reviews

Ibis Bay Beach Resort

The Perry Hotel & Marina Key West

Parrot Key Hotel & Villas

Hyatt Vacation Club at Beach House, Key West

Hampton Inn Key West FL

Beachside Resort & Residences

Hyatt Vacation Club at Windward Pointe, Key West

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Find Hotels with a Pool in Cudjoe Key, FL

Upfront pricing

Treat yourself

Be picky

Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

1. Parmer's Resort

2. Sugar Loaf Lodge

3. Looe Key Reef Resort

4. Atlantic View Luxury Villa with Pool

5. Old Wooden Bridge Resort and Marina

6. Hilton Key West Resort & Marina

7. Hampton Inn Key West FL

8. Hilton Garden Inn Key West / The Keys Collection

9. Beachside Resort & Residences

10. DoubleTree Resort by Hilton Grand Key - Key West

Choose what matters most at hotels with a pool in Cudjoe Key

Top Cudjoe Key Hotel Reviews

Ibis Bay Beach Resort

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