Sugarloaf Key Holiday Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Sugarloaf Key holiday rentals
1. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
Tom H.
The price is HK$1,546
HK$4,692 total
includes taxes & fees
7 Sept - 8 Sept
2. Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
max
The price is HK$2,129
HK$5,113 total
includes taxes & fees
16 Aug - 17 Aug
3. The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key WestUpper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
Brian K.
8.6 out of 10, Excellent, (364 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
Kathy
The price is HK$706
HK$1,898 total
includes taxes & fees
1 Sept - 2 Sept
5. SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
James B.
The price is HK$1,169
HK$3,405 total
includes taxes & fees
16 Aug - 17 Aug
6. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
David T.
The price is HK$1,169
HK$3,421 total
includes taxes & fees
12 Aug - 13 Aug
7. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe KeyCudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
Kiara
The price is HK$1,553
HK$4,708 total
includes taxes & fees
24 Aug - 25 Aug
8. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWSCudjoe Key
9.8 out of 10, Exceptional, (32 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
BRIAN S.
The price is HK$1,590
HK$3,398 total
includes taxes & fees
21 Aug - 22 Aug
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find holiday rentals that suit your style
Houseboats
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Sugarloaf Key Hotel Reviews
Margaritaville Beach House Key West
10/10 Excellent
Find out more about Sugarloaf Key
Search for holiday rentals in Sugarloaf Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Sugarloaf Key using one of the methods below:
- View our selection of featured holiday rentals in Sugarloaf Key
- Use the map to find apartments and other holiday homes in the Sugarloaf Key neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Sugarloaf Key while they last
Look no further and take a look at our great range of rental properties in Sugarloaf Key!
Explore a world of travel with Expedia
- 5 Star Hotels in Melody Key
- Aparthotels in Ramrod Key
- Motels in Summerland Key
- Apartments in Summerland Key
- Casa Marina Hotels
- 4 Star Hotels in Ramrod Key
- B&B in Ramrod Key
- Family Hotel Hotels in Cudjoe Key
- Hotels near National Key Deer Refuge Visitor Center
- Midtown Hotels
- Hotels near Key West Tropical Forest and Botanical Garden
- Hotels near Florida Keys Beaches
- Vacation Homes in Key Haven
- Hotels near Looe Key National Marine Sanctuary
- Resorts in Cow Key
- B&B in Summerland Key
- Rv Parks in Ramrod Key
- Rv Parks in Summerland Key
- Vacation Homes in Little Torch Key
- Apartments in Boca Chica Key
- Lgbt Welcoming Hotel Hotels in Ramrod Key
- 3 Star Hotels in Stock Island
- Aparthotels in Big Torch Key
- Apartments in Lower Keys
- Hyatt Hotels in Cow Key
- Resorts in Stock Island
- Resorts in Cudjoe Key
- Independent Hotels in Ramrod Key
- Hotels near Smathers Beach
- Wyndham Hotels in Sugarloaf Shores
- Resorts in Little Torch Key
- Houseboats in Cow Key
- Condo Rentals in Summerland Key
- Boutique Hotel Hotels in Stock Island
- Sands Hotels
- Noble House Hotels in Rockland Key
- Flights from Chos Malal (HOS) to Key West (EYW)
- Flights from Fairbanks (FAI) to Key West (EYW)
- Flights from Tuntutuliak (WTL) to Key West (EYW)
- Flights from Los Angeles (LAX) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- American Airlines San Francisco (SFO) to Key West (EYW) flights
- Silver Airways Tampa (TPA) to Key West (EYW) flights
- Flights from Budapest (BUD) to Key West (EYW)
- Flights from Melody Key
- Flights from Macon (MCN) to Key West (EYW)
- Flights from Winter Haven (GIF) to Key West (EYW)
- Flights from Destin (DSI) to Key West (EYW)
- Flights from Olathe (OJC) to Key West (EYW)
- Flights from Page (PGA) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- American Airlines Dallas (DFW) to Key West (EYW) flights
- American Airlines New York (LGA) to Key West (EYW) flights
- Flights to Cudjoe Key
- Flights from Kaunas (KUN) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Jaisalmer (JSA) to Key West (EYW)
- Flights to Stock Island
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from New York (NYC) to Key West (EYW)
- Flights from Gainesville (GNV) to Key West (EYW)
- Flights from Big Pine Key
- Flights from Key Haven
- Flights from Bartow (BOW) to Key West (EYW)
- Flights from St. Augustine (UST) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Daegu (TAE) to Key West (EYW)
- Flights from Punta Gorda Airport (PGD) to Key West (EYW)
- Flights from Willemstad (CUR) to Key West (EYW)
- Flights from Little Torch Key
- Flights to Big Pine Key
- Delta Seattle (SEA) to Key West (EYW) flights
- American Airlines Baltimore (BWI) to Key West (EYW) flights
- Flights from Valdosta (VLD) to Key West (EYW)
- Flights from Kissimmee (ISM) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Hong Kong (HKG) to Key West (EYW)
- Flights to Melody Key
