A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Key Hotel with Pool

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Check availability on Sugarloaf Key Hotel with Pool

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Sugarloaf Key hotels with a pool

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
HK$934
HK$1,050 total
includes taxes & fees
4 Oct - 5 Oct
Sugar Loaf Lodge

2. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
HK$1,299
HK$1,462 total
includes taxes & fees
7 Oct - 8 Oct
Hampton Inn Key West FL

3. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
HK$2,746
HK$5,971 total
includes taxes & fees
9 Oct - 10 Oct
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

4. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
HK$3,089
HK$5,882 total
includes taxes & fees
2 Oct - 3 Oct
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

5. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
  • Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.
HK$982
HK$1,325 total
includes taxes & fees
7 Oct - 8 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

6. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
HK$994
HK$1,374 total
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort

7. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
HK$1,091
HK$3,286 total
includes taxes & fees
4 Oct - 5 Oct
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

8. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
HK$3,707
HK$6,655 total
includes taxes & fees
2 Oct - 3 Oct
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

9. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
  • Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.
HK$935
HK$1,317 total
includes taxes & fees
8 Oct - 9 Oct
DoubleTree Resort by Hilton Grand Key - Key West

10. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
HK$3,213
HK$6,525 total
includes taxes & fees
2 Oct - 3 Oct
Post Card Point #319 - Ocean Views!
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view."
Keith 7-night trip
Posted 4 hours ago
Southernmost Beach Resort and Guesthouses
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Had a great time!"
Nathan 4-night trip
Posted 6 hours ago
Winslow's Bungalows - Key West Historic Inns
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The room was clean. No daily housekeeping. The staff were pleasant and quiet helpful. Breakfast was outstanding. It was alacart and you have to pay per item. Over all this was the most relaxing vacation I've been on. Loved it!"
Harry 1-night trip
Posted 12 hours ago
Beachside Resort & Residences
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted 1 day ago
Parrot Key Hotel & Villas
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Amazing place to stay for vacation."
David 5-night trip
Posted 1 day ago
Casa Marina Key West, Curio Collection by Hilton
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"
Christy 2-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Thank you"
Agustin 2-night trip
Posted 2 days ago
Hilton Garden Inn Key West / The Keys Collection
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

8/10 Good
"Good place to stay but watch out for the gratuity tax (it's a State of Florida thing). The property was well maintained, and we enjoyed the room. Overall, it was a good place to stay. Most of the staff were hospitable and management was amazing."
April 5-night trip
Posted 3 days ago
The Perry Hotel & Marina Key West

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