Lower Keys Holiday Rentals

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Our top choices for Lower Keys holiday rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is NZ$587
includes taxes & fees
4 Jan - 5 Jan 2026
Sunshine Key RV Resort & Marina

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (52)
"Great area. Quiet and comfortable "
United States
nancy c.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, just minutes to Key West!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (12)
"The owners were fantastic to deal with and the house was great. "
United States
Anonymous traveller
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
9.4 out of 10, Exceptional, (3)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
The price is NZ$506
includes taxes & fees
13 Jan - 14 Jan 2026
Star Room Barnacle Resort

🌴 TROPICAL RETREAT 🌴 RV in the Keys

🌴 TROPICAL RETREAT 🌴 RV in the Keys
Big Pine Key
10.0 out of 10, Exceptional, (2)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
United States
DeeBrett
The price is NZ$599
includes taxes & fees
3 Jan - 4 Jan 2026
🌴 TROPICAL RETREAT 🌴 RV in the Keys

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

DECEMBER SAVE 60% OFF! 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$1,044
includes taxes & fees
10 Jan - 11 Jan 2026
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is NZ$1,757
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (122)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
Kelly's Kabin - Adorable Private Summerland Key Cottage

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1)
The price is NZ$514
includes taxes & fees
30 Dec - 31 Dec
Seabreeze Escape WF RV Lot 489

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴
Big Pine Key
The price is NZ$649
includes taxes & fees
3 Jan - 4 Jan 2026
🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

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$3,909
includes taxes & fees
3 Jan - 4 Jan 2026
The Hemingway - Beach Houses Key West

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

DECEMBER SAVE 60% OFF 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$1,044
includes taxes & fees
18 Jan - 19 Jan 2026
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
The price is NZ$510
includes taxes & fees
27 Dec - 28 Dec
Endless Summer Hideaway - lot 181

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$1,053
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,486
includes taxes & fees
7 Jan - 8 Jan 2026
Starlight Serenity - Hideaway w Stunning Views

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$1,221
includes taxes & fees
4 Jan - 5 Jan 2026
Spanish Queen @Venture Out, Cudjoe Key

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is NZ$4,258
includes taxes & fees
4 Jan - 5 Jan 2026
The Lighthouse - 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.
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Top Lower Keys Hotel Reviews

Find out more about Lower Keys

Everything you need to know about Lower Keys holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lower Keys holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lower Keys holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lower Keys holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lower Keys. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lower Keys holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lower Keys holiday rentals we have selected for you start as low as NZ$587 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lower Keys rentals

At Expedia, we put the best Lower Keys holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lower Keys rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lower Keys holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lower Keys. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.