A coastal road with a beach on one side and a marina with boats on the other.

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Check prices for these dates

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct
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Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 16 hours ago
Sugar Loaf Lodge
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Great place for the family."
JUAN 2-night trip
Posted 1 day ago
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"KOA PROPERTY"
Ronald 2-night trip
Posted 2 days ago
Sugarloaf Key Hotel at KOA Resort
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent
"Everything was great! The house and the pool were clean and the basketball goal was an added plus! We wished that there were pool/beach towels in the house, but other than that everything was perfect!"
Bevan B. 4-night trip
Posted 4 days ago
Private Secluded Ocean View & Pool Near Key West
Oceanside Paradise  Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent
"We had a great stay! Everything was clean, comfortable, and worked out perfectly for our trip. Having access to the boat ramp and convenient parking for both our boat and trailer was extremely helpful. The marina store was a nice added convenience, and having a pressure washer available made cleaning up after a day on the water much easier. Overall, we really enjoyed our stay and would definitely stay here again."
Sterling D. 2-night trip
Posted 5 days ago
Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

8/10 Good
"Convenient location."
Lisa 3-night trip
Posted 2 weeks ago
Direct Oceanfront Cottage-Sunrise View- #2,
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

10/10 Excellent
"Cottage was clean. We enjoyed the stay. Needs an outlet cover in living room."
Valinda T. 7-night trip
Posted 2 weeks ago
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

10/10 Excellent
"Our three-night stay at this exceptional waterfront retreat was nothing short of extraordinary. Set against sweeping open-water views, the property offers that rare combination of effortless comfort, understated elegance, and a truly idyllic setting.From the moment we arrived, the home felt like a private escape designed for relaxation. The interiors were inviting and beautifully maintained, while the waterfront setting provided a spectacular backdrop throughout our stay. Mornings overlooking the water and quiet evenings by the dock were among the many memorable moments.The private dock and golf cart elevated the experience even further, making it wonderfully easy to explore the community and enjoy everything the resort has to offer. Every detail seemed to encourage slowing down, savoring the surroundings, and simply enjoying being there.Although we stayed only three nights, the experience felt wonderfully restorative—and we found ourselves wishing we had booked a much longer stay. This is the kind of place where the pace immediately changes, the views become part of the experience, and a short getaway feels like a true escape.Beautifully situated, exceptionally comfortable, and surrounded by breathtaking waterfront scenery, this home is a destination in itself. We would return without hesitation and look forward to our next visit. A truly memorable stay in a spectacular setting. Host Mel is wonderful and very attentive."
Ammad H. 3-night trip
Posted 3 weeks ago
Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

8/10 Good
"Nice for a chill weekend in the lower keys and for people with family accompanying them"
Janey 3-night trip
Posted 3 weeks ago
Sugarloaf Key RV Resort & Cottages