Holiday Homes in Lower Sugarloaf Key

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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Lower Sugarloaf Key holiday homes

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

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

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is NZ$1,045
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,045
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
House
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is NZ$5,715
includes taxes & fees
20 Jan - 21 Jan 2026
Waterfront Luxury Home - Tidelands House
Pool
The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
The price is NZ$4,559
includes taxes & fees
4 Jan - 5 Jan 2026
The Shellstone House at Solaire Lunara Bay
Pool
The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is NZ$3,914
includes taxes & fees
3 Jan - 4 Jan 2026
The Hemingway - Beach Houses Key West
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.

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

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is NZ$2,255
includes taxes & fees
7 Jan - 8 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.
A heated pool
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
The price is NZ$1,054
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pool
Mirador House at Lunara Bay

Mirador House at Lunara Bay

Mirador House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (33)
"House was very clean and exactly as shown on the listing. Our group was 15 and it was perfect. The only issue was there were no griddles or pans for the stove/oven. Only pots were provided. We requested pans and they brought them to us. "
United States
Alex M.
The price is NZ$3,609
includes taxes & fees
20 Jan - 21 Jan 2026
Mirador House at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is NZ$2,711
includes taxes & fees
12 Jan - 13 Jan 2026
Springtide House at Lunara Bay
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is NZ$1,424
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
Terrace/patio
The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,713
includes taxes & fees
4 Jan - 5 Jan 2026
The Seagate Estate at Lunara Bay
Terrace/patio
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays

Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays

Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
Old Town Key West
9.0 out of 10, Wonderful, (180)
"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "
United States
ALISHA
The price is NZ$880
includes taxes & fees
16 Jan - 17 Jan 2026
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
House
Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NZ$3,310
includes taxes & fees
20 Jan - 21 Jan 2026
Capmar House by Brightwild Huge Home Pool
Outdoor dining
Poolside Cottage #412

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (28)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
The price is NZ$654
includes taxes & fees
7 Jan - 8 Jan 2026
Poolside Cottage #412
Outdoor dining
Poolside Cottage #411

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
The price is NZ$941
includes taxes & fees
3 Jan - 4 Jan 2026
Poolside Cottage #411
Outdoor dining
Larkshine House at Lunara Bay

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is NZ$4,232
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19)
"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 NZ$1,223
includes taxes & fees
4 Jan - 5 Jan 2026
Spanish Queen @Venture Out, Cudjoe Key
A heated pool
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
Cudjoe Key
The price is NZ$1,154
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Pool
105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is NZ$1,334
includes taxes & fees
21 Jan - 22 Jan 2026
105 - Newly renovated house Oceanside and Pool
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.
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Top Lower Sugarloaf Key Hotel Reviews

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We didn't know there was breakfast until this survey! How did we miss it? The pet friendliness was great. Our dog was happy about the grass out front and the availability of ice. She loves ice."
Eric 2-night trip
Posted 18 hours ago
Hyatt Centric Key West Resort and Spa

Find out more about Lower Sugarloaf Key

Lower Sugarloaf Key Holiday Homes information

Number of reviews
671
Accommodation
807 Holiday Homes
Lowest Price
NZ$654
Highest Price
NZ$5,715

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