Lower Sugarloaf Key Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Lower Sugarloaf Key

Charming 3-bedroom house in Big Pine Key near Beach and Key West

The price is NZ$983
includes taxes & fees
27 July - 28 July
Charming 3-bedroom house in Big Pine Key near Beach and Key West

🌴 TROPICAL RETREAT 🌴 RV in the Keys

The price is NZ$598
includes taxes & fees
6 Aug - 7 Aug
🌴 TROPICAL RETREAT 🌴 RV in the Keys

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (64)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is NZ$2,205
includes taxes & fees
12 Aug - 13 Aug
One of the very few beach houses with a daily, rental license in the Keys.

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
Kelly's Kabin - Adorable Private Summerland Key Cottage

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.0 out of 10, Wonderful, (4)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is NZ$1,402
includes taxes & fees
23 Aug - 24 Aug
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
The price is NZ$1,423
includes taxes & fees
17 Aug - 18 Aug
Post Card Point #319 - Ocean Views!

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is NZ$822
includes taxes & fees
10 Aug - 11 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is NZ$1,018
includes taxes & fees
18 Aug - 19 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
The price is NZ$1,132
includes taxes & fees
6 Aug - 7 Aug
Spanish Queen @Venture Out, Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is NZ$927
includes taxes & fees
2 Aug - 3 Aug
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (6)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is NZ$1,018
includes taxes & fees
19 Aug - 20 Aug
Island Time #110 Ocean Views - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

9.4 out of 10, Exceptional, (26)
"The property was beautiful enjoyed the porch sitting and taking the kayaks and bikes out "
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
The price is NZ$783
includes taxes & fees
3 Aug - 4 Aug
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (114)
"Great place to get away. House and property were nice. If your bring a boat, you have to watch the tides. Flats or a smaller bay boat will be fine. Had a 21 foot center console. Low tide you just have to take it slow out to the channel. Great options for docking your boat. A lot of space for boat trailers. Location of property is nicely situated. "
The price is NZ$892
includes taxes & fees
3 Aug - 4 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is NZ$1,363
includes taxes & fees
25 July - 26 July
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

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

8.8 out of 10, Excellent, (85)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is NZ$1,147
includes taxes & fees
25 July - 26 July
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (10)
"I loved the secluded nature of the property it felt like we had the whole place to ourselves. Beach was beautiful and the property manager was very responsive. The location is close enough to Key West that it’s easy to do an excursion or go to dinner. "
Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (1)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
The price is NZ$5,811
includes taxes & fees
30 July - 31 July
Private and Exclusive Beach Getaway

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"
The price is NZ$1,760
includes taxes & fees
4 Aug - 5 Aug
The Lighthouse - Beach Houses Key West

The Hemingway - Beach Houses Key West

9.8 out of 10, Exceptional, (7)
"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"
The Hemingway - Beach Houses Key West
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lower Sugarloaf Key Hotel Reviews