Search Vacation Homes in Lower Sugarloaf Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search 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 Lower Sugarloaf Key holiday homes

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

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.8 out of 10, Excellent, (3 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is HK$2,727
HK$6,017 total
includes taxes & fees
1 Mar - 2 Mar
Charming 3-bedroom house in Big Pine Key near Beach and Key West

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (84 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$1,946
HK$4,349 total
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is HK$1,555
HK$3,862 total
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is HK$2,149
HK$4,759 total
includes taxes & fees
1 Mar - 2 Mar
Kelly's Kabin - Adorable Private Summerland Key Cottage

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
The price is HK$1,957
HK$5,257 total
includes taxes & fees
3 Mar - 4 Mar
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is HK$2,735
HK$5,349 total
includes taxes & fees
24 Feb - 25 Feb
Spanish Queen @Venture Out, Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (8 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is HK$1,551
HK$4,714 total
includes taxes & fees
22 Mar - 23 Mar
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Fun in the Sun in Cudjoe Key! #51

Fun in the Sun in Cudjoe Key! #51
Cudjoe Key
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is HK$1,797
HK$5,406 total
includes taxes & fees
9 Mar - 10 Mar
Fun in the Sun in Cudjoe Key! #51

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is HK$4,255
HK$9,054 total
includes taxes & fees
25 Feb - 26 Feb
Private and Exclusive Florida Keys Getaway

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (151 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is HK$2,930
HK$5,696 total
includes taxes & fees
23 Feb - 24 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is HK$1,934
HK$3,989 total
includes taxes & fees
7 Mar - 8 Mar
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$2,667
HK$6,079 total
includes taxes & fees
6 Mar - 7 Mar
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is HK$3,017
HK$6,653 total
includes taxes & fees
24 Mar - 25 Mar
105 - Newly renovated house Oceanside and Pool

Ocean Vue in Cudjoe Key 469

Ocean Vue in Cudjoe Key 469
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"The place was great. The location was excellent. The view was amazing. We will be back!"
United States
Rob M.
The price is HK$2,022
HK$5,690 total
includes taxes & fees
13 Mar - 14 Mar
Ocean Vue in Cudjoe Key 469

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
8.6 out of 10, Excellent, (91 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is HK$2,813
HK$6,043 total
includes taxes & fees
1 Mar - 2 Mar
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is HK$3,188
HK$6,763 total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway with Stunning Views

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The Hemingway - Beach Houses Key West

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (52 reviews)
"New furniture, and outfitting. Great view. Possibly the best location in the community. Steps from the boat ramp. "
United States
Matthew K.
The price is HK$3,282
HK$7,430 total
includes taxes & fees
28 Feb - 1 Mar
Post Card Point #319 - Ocean Views!

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
9.8 out of 10, Exceptional, (143 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is HK$3,898
HK$7,714 total
includes taxes & fees
11 Mar - 12 Mar
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Tiki Time in Cudjoe Key 136

Tiki Time in Cudjoe Key 136
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful well maintained property. You just cannot beat the view on the extra large deck. Sit back relax and enjoy a coffee.I absolutely love this property."
Canada
Rachel H.
The price is HK$2,696
HK$6,542 total
includes taxes & fees
13 Mar - 14 Mar
Tiki Time in Cudjoe Key 136
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

Find out more about Lower Sugarloaf Key

Lower Sugarloaf Key Vacation Homes information

Number of reviews
826
Accommodation
821 Vacation Homes
Lowest Price
HK$3,862
Highest Price
HK$9,054

Explore a world of travel with Expedia