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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Lower Keys vacation homes

Outdoor dining
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Cudjoe Key

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is AED 547
AED 1,594 total
includes taxes & fees
14 Dec - 15 Dec
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage

Vacation Home in Summerland Key

Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is AED 744
AED 1,886 total
includes taxes & fees
14 Dec - 15 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
Smart TV, books
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Vacation Home in Sands

Charming 3-bedroom house in Big Pine Key near Beach and Key West
The price is AED 694
AED 2,086 total
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Outdoor pool, a heated pool
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Vacation Home in Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
7.6 out of 10, Good, (13)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is AED 819
AED 1,751 total
includes taxes & fees
6 Jan - 7 January 2026
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool
Island Time #110 Ocean Views - Cudjoe Key

Vacation Home in Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 868
AED 2,386 total
includes taxes & fees
11 Dec - 12 Dec
Island Time #110 Ocean Views - Cudjoe Key
House | 2 bedrooms, Internet
Starlight Serenity - Hideaway w Stunning Views

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is AED 967
AED 2,316 total
includes taxes & fees
11 Dec - 12 Dec
Starlight Serenity - Hideaway w Stunning Views
Outdoor pool, a heated pool
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Vacation Home in Cudjoe Key

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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 AED 915
AED 2,055 total
includes taxes & fees
14 Dec - 15 Dec
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Fridge, microwave, oven, stovetop
Starlight Serenity - Hideaway with Stunning Views

Vacation Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views
The price is AED 690
AED 2,144 total
includes taxes & fees
11 Dec - 12 Dec
Starlight Serenity - Hideaway with Stunning Views
A heated pool
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Vacation Home in Cudjoe Key

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
The price is AED 694
AED 2,177 total
includes taxes & fees
18 Dec - 19 Dec
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Vacation Home in Cutthroat Harbor Estates

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
The price is AED 826
AED 1,969 total
includes taxes & fees
11 Dec - 12 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Pool
Palm - Beach Houses Key West

Vacation Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
Palm - Beach Houses Key West
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, 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 AED 1,285
AED 2,499 total
includes taxes & fees
15 Dec - 16 Dec
Spanish Queen @Venture Out, Cudjoe Key
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.

Vacation Home in Summerland Key

One of the very few beach houses with a daily, rental license in the Keys.
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is AED 1,980
AED 4,833 total
includes taxes & fees
15 Dec - 16 Dec
One of the very few beach houses with a daily, rental license in the Keys.
A heated pool
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Vacation Home in Cudjoe Key

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
The price is AED 771
AED 2,267 total
includes taxes & fees
11 Dec - 12 Dec
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A heated pool
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Vacation Home in Cudjoe Key

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
2.0 star property
The price is AED 868
AED 2,339 total
includes taxes & fees
11 Dec - 12 Dec
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
A heated pool
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Vacation Home in Cudjoe Key

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
The price is AED 964
AED 2,444 total
includes taxes & fees
4 Jan - 5 January 2026
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
A heated pool
Galleon Getaway #533- Oceanfront Community

Vacation Home in Cudjoe Key

Galleon Getaway #533- Oceanfront Community
The price is AED 752
AED 2,242 total
includes taxes & fees
11 Dec - 12 Dec
Galleon Getaway #533- Oceanfront Community
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

Vacation Home in Little Torch Key

Old Florida Style, wrap around porch, boat basin for dockage, open water
9.6 out of 10, Exceptional, (86)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is AED 1,653
AED 3,230 total
includes taxes & fees
26 Dec - 27 Dec
Old Florida Style, wrap around porch, boat basin for dockage, open water
A heated pool
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Vacation Home in Cudjoe Key

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
The price is AED 771
AED 2,267 total
includes taxes & fees
11 Dec - 12 Dec
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool
Reel Island Retreat #273 at Venture Out in the Florida Keys

Vacation Home in Cudjoe Key

Reel Island Retreat #273 at Venture Out in the Florida Keys
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
The price is AED 1,060
AED 2,629 total
includes taxes & fees
11 Dec - 12 Dec
Reel Island Retreat #273 at Venture Out in the Florida Keys
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 Keys Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Great place to stary. Staff was very nice."
norka 1-night trip
Posted 3 days ago
Sugar Loaf Lodge