Vacation rentals in Rockland Key

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Top vacation rentals in Rockland Key

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
4.69 mi from city center
$355 nightly
The price is $400 total per night
$400 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This houseboat features a marina and free WiFi in public areas. Take advantage of the free self parking.
Parking included
Free WiFi
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

2 out of 5
Key West FL
4.99 mi from city center
$512 nightly
The price is $576 total per night
$576 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stay at this aparthotel in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence

2 out of 5
Key West FL
4.99 mi from city center
$657 nightly
The price is $739 total per night
$739 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stay at this aparthotel in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
Pet friendly
Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access

2 out of 5
Key West FL
4.99 mi from city center
$724 nightly
The price is $815 total per night
$815 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stay at this aparthotel in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
Pet friendly
Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

Key West FL
8.43 mi from city center
$337 nightly
The price is $374 total per night
$374 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
An outdoor pool is featured at this apartment, along with laundry facilities and barbecue grills.
Pool
Kitchen
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
1445 S Roosevelt Blvd Key West FL
5.03 mi from city center
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This condo's 2 outdoor pools and hot tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
Pool
Hot Tub
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Key West FL
8.44 mi from city center
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Free WiFi in public areas is available at this cottage.
Kitchen
Washer
Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline

Key West FL
8.32 mi from city center
$787 nightly
The price is $874 total per night
$874 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Naval Air Station Key West FL
4.33 mi from city center
$451 nightly
The price is $501 total per night
$501 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This houseboat features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Key West FL
8.08 mi from city center
$545 nightly
The price is $600 total per night
$600 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Washer
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

Key West FL
8.43 mi from city center
$433 nightly
The price is $477 total per night
$477 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
This condo features laundry facilities.
Pool
Kitchen
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Key West FL
5.31 mi from city center
$567 nightly
The price is $629 total per night
$629 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This condo features an outdoor pool and a gym. Laundry facilities and barbecue grills are also provided.
Pool
Kitchen
Heated Pool, Steps to Duval St - Poolside Paradise

Heated Pool, Steps to Duval St - Poolside Paradise

Key West FL
8.22 mi from city center
$1,751 nightly
The price is $1,943 total per night
$1,943 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Walk to Duval, Private Pool - Keys Breeze

Walk to Duval, Private Pool - Keys Breeze

Key West FL
8.15 mi from city center
$1,445 nightly
The price is $1,609 total per night
$1,609 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This vacation home features a water park, a garden, and laundry facilities.
Pool
Kitchen
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

Key West FL
6.97 mi from city center
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This condo features a gym and a hot tub. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
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See all available properties in Rockland Key
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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.

The Best Way to Find your Vacation Rentals in Rockland Key

How cheap can a vacation rental in Rockland Key be?

You can find vacation rentals in Rockland Key for as low as $374 per night.

How do you look for the best vacation rental deals in Rockland Key with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Rockland Key so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Rockland Key can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Rockland Key?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Rockland Key vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Rockland Key?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Rockland Key vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Rockland Key?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Rockland Key vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.