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

Find Hotels with a Pool in Sugarloaf Key, FL

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Sugarloaf Key Hotels with a Pool

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
$99 nightly
$111 total
Sep 27 - Sep 28
Total with taxes and fees
Sugar Loaf Lodge

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$92 nightly
$104 total
Sep 27 - Sep 28
Total with taxes and fees
Looe Key Reef Resort

3. Old Wooden Bridge Resort and Marina

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
$253 total
Sep 27 - Sep 28
Total with taxes and fees
Old Wooden Bridge Resort and Marina

4. 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.
$173 nightly
$194 total
Oct 4 - Oct 5
Total with taxes and fees
Parmer's Resort

5. Hilton Key West Resort & Marina

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.
$162 nightly
$182 total
Sep 24 - Sep 25
Total with taxes and fees
Hilton Key West Resort & Marina

6. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
  • Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.
$168 nightly
$189 total
Sep 24 - Sep 25
Total with taxes and fees
The Perry Hotel & Marina Key West

7. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$185 nightly
$208 total
Sep 27 - Sep 28
Total with taxes and fees
Beachside Resort & Residences

8. 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.
$133 nightly
$150 total
Sep 30 - Oct 1
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West

9. 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.
$135 nightly
$152 total
Sep 27 - Sep 28
Total with taxes and fees
Hampton Inn Key West FL

10. Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
  • Splash into paradise at this Art Deco hotel with a poolside bar and marina access.
$130 nightly
$146 total
Sep 24 - Sep 25
Total with taxes and fees
Ibis Bay Beach Resort
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

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"Nice, spacious rooms. Nice Pool and fantastic bar tender! Maintenance speedy if needed. Nice to have the shuttle to/from downtown. Enjoyed our stay very much."
Karen 4-night trip
Posted 4 hours ago
Beachside Resort & Residences
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Beautiful ambiance."
charles 2-night trip
Posted 5 hours ago
Casa Marina Key West, Curio Collection by Hilton
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Friendly and helpful staff. Love the 2 pools. It's great that they have a complimentary shuttle to take you downtown."
Melissa 1-night trip
Posted 5 hours ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Tyrone was extremely helpful with any need that came up. Even when it was not his responsibility, he made sure we were taken care of"
Benjamin Neil 3-night trip
Posted 7 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Me encantó la verdad muy limpio trankilo y para ir en familia y con niños lo recomiendo mucho gracias"
Suany 2-night trip
Posted 1 day ago
Hampton Inn Key West FL
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 1 day ago
Ibis Bay Beach Resort
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"This was our second time staying at The Perry and this time we brought friends. The location on the marina is really nice and there are restaurants nearby, like Roostica! We did notice from our 1st stay that the rooms are needing a little TLC regarding maintenance and repairs. Nothing serious, just an observation. BONUS they have an hourly shuttle to/from Key West! We will stay here again!"
Jamie 1-night trip
Posted 1 day ago
The Perry Hotel & Marina Key West

Explore a world of travel with Expedia