Short-Term Rentals in Rockland Key, FL: Compare 10+ Sites & Save

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  6.  Rockland Key

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396 Best Short-Term Rentals in Rockland Key (Starting from $143)

Dock and Balcony Serene Big Coppitt Key Escape
Dock and Balcony Serene Big Coppitt Key Escape
House
Key West, FL, USA
2.1k from Rockland Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$281
Average price / night
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The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West
The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West
House
Key West, FL, 33040, United States
1.0k from Rockland Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
New to Booking
$401
Average price / night
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Sapphire Sabbatical
Sapphire Sabbatical
House
Key West, FL, USA
2.4k from Rockland Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$253
Average price / night
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House, deck, dock, navigable channel to open sea, 10 min. driving to Duval St.
House, deck, dock, navigable channel to open sea, 10 min. driving to Duval St.
House
Key West, FL, 33040, United States
1.1k from Rockland Key center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$227
Average price / night
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Jewel on Jade
Jewel on Jade
House
Key West, FL, USA
2.6k from Rockland Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
New to Booking
$197
Average price / night
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Sunsets over the water
Sunsets over the water
Condo
Key West, FL, 33040, United States
1.2k from Rockland Key center

AC, Internet, No Smoking, TV

1 Bedroom4 Guests
New to Booking
$143
Average price / night
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Ritaville - Monthly Rental
Ritaville - Monthly Rental
House
Stock Island, FL, USA
2.8k from Rockland Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms11 Guests
New to Booking
$641
Average price / night
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Ocean Front, Private home with Boat Dock, 3 bedroom
Ocean Front, Private home with Boat Dock, 3 bedroom
House
Key West, FL, 33040, United States
1.3k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$356
Average price / night
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Parking Pool & Dock - Shellstone House
Parking Pool & Dock - Shellstone House
House
Key West, FL, USA
5.5k from Rockland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$3262
Average price / night
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Mermaid Landing, with Private Beach and Mini Golf Course
Mermaid Landing, with Private Beach and Mini Golf Course
House
Key West, FL, 33040, United States
1.8k from Rockland Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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The Fairhaven House at Solaire Lunara Bay
The Fairhaven House at Solaire Lunara Bay
House
Key West, FL, USA
5.5k from Rockland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom16 Guests
New to Booking
$3719
Average price / night
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Seaside Cottage minutes to Key West
Seaside Cottage minutes to Key West
House
Key West, FL, 33040, United States
2.0k from Rockland Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, No Smoking, TV, Washer

1 Bedroom6 Guests
New to Booking
$316
Average price / night
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Parking Pool Dock - Starboard House
Parking Pool Dock - Starboard House
House
Key West, FL, USA
5.6k from Rockland Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms20 Guests
New to Booking
$2900
Average price / night
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**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
2.1k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$757
Average price / night
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Waterfront Luxury Home - Tidelands House
Waterfront Luxury Home - Tidelands House
House
Key West, FL, USA
5.6k from Rockland Key center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$3045
Average price / night
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Fisherman's Paradise on the Water
Fisherman's Paradise on the Water
House
Key West, FL, 33040, United States
2.3k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$369
Average price / night
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New Waterfront Home - Dreamside House
New Waterfront Home - Dreamside House
House
Key West, FL, USA
5.6k from Rockland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$1924
Average price / night
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Blue Gem | Family-Friendly Waterfront  w/Pool, Tiki Bar/Dock (Monthly Stay)
Blue Gem | Family-Friendly Waterfront w/Pool, Tiki Bar/Dock (Monthly Stay)
House
Key West, FL, 33040, United States
2.4k from Rockland Key center

AC, Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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The Joyrise House at Solaire Lunara Bay
The Joyrise House at Solaire Lunara Bay
House
Key West, FL, USA
5.6k from Rockland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$5185
Average price / night
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Beautiful 3 bedroom 2 bath pool house close to Key West
Beautiful 3 bedroom 2 bath pool house close to Key West
House
Big Coppitt Key, FL, 33040, United States
2.4k from Rockland Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$400
Average price / night
Check Availability
New Waterfront Home - Sunray House
New Waterfront Home - Sunray House
House
Key West, FL, USA
5.7k from Rockland Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$3045
Average price / night
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Waterfront, Single-Story Home on a Canal w/ Dock, Kayaks, AC - 1 Small Dog OK
Waterfront, Single-Story Home on a Canal w/ Dock, Kayaks, AC - 1 Small Dog OK
House
Key West, FL, 33040, United States
2.4k from Rockland Key center

3 Bedrooms6 Guests
New to Booking
$190
Average price / night
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Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
House
Big Coppitt Key, FL, 33040, United States
2.4k from Rockland Key center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
New to Booking
$608
Average price / night
Check Availability
Private Paradise, Waterfront Home - 15 minutes from Key West
Private Paradise, Waterfront Home - 15 minutes from Key West
House
Key West, FL, 33040, United States
2.5k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$499
Average price / night
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Canalside condo with private dock, boat ramp, water-view patio, central AC & W/D
Canalside condo with private dock, boat ramp, water-view patio, central AC & W/D
House
Key West, FL, 33040, United States
2.6k from Rockland Key center

2 Bedrooms6 Guests
New to Booking
$245
Average price / night
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Breathtaking Ocean views with immediate Ocean access!  Welcome home!
Breathtaking Ocean views with immediate Ocean access! Welcome home!
House
Geiger Key, FL, 33040, United States
2.7k from Rockland Key center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Washer

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$368
Average price / night
Check Availability
The Local's favorite spot.
The Local's favorite spot.
House
Key West, FL, 33040, United States
2.7k from Rockland Key center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$321
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Rockland Key.

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Rockland Key Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 396 verified short-term rentals in Rockland Key, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Rockland Key vary depending on location, property size, and travel dates. Rates typically start from around $143 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Rockland Key include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Rockland Key, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Rockland Key often include amenities such as View, Wellness Facilities, and Pool, providing a comfortable and convenient stay.

Short-term rentals in Rockland Key are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.