Oceanfront Rentals in Rockland Key, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Rockland Key

Refine your search

Price per night

Amenity Filter

Rating

160 Best Oceanfront Rentals in Rockland Key (Starting from $196)

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
Check Availability
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
Check Availability
Oceans Edge Key West
Oceans Edge Key West
Resort
Rockland Key, Key West, Florida, USA
6.0k from Rockland Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Places to stay

171 Bedrooms38 Guests
8.5

Very Good

1216 reviews

$884
Average price / night
Check Availability
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
Check Availability
Key West Home on Golf Course with Patio and Grill!
Key West Home on Golf Course with Patio and Grill!
House
Key West, FL, USA
6.6k from Rockland Key center

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

2 Bedrooms4 Guests
New to Booking
$215
Average price / night
Check Availability
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
Check Availability
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
Resort
Key West, USA
7.0k from Rockland Key center

Luxury, Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay

100 Bedrooms46 Guests
8.9

Fabulous

444 reviews

$883
Average price / night
Check Availability
**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
Check Availability
Beachside Resort & Residences
Beachside Resort & Residences
Resort
Key West, FL, USA
8.0k from Rockland Key center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Beach, Hot tubs

185 Bedrooms60 Guests
8.0

Good

1075 reviews

$224
Average price / night
Check Availability
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
Check Availability
DoubleTree by Hilton Grand Key Resort
DoubleTree by Hilton Grand Key Resort
Resort
Key West, FL, USA
8.3k from Rockland Key center

Accommodations, Pools, Resorts, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Family

216 Bedrooms38 Guests
7.3

Good

652 reviews

$196
Average price / night
Check Availability
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
Check Availability
Sunrise Condo At Seaside - Key West!
Sunrise Condo At Seaside - Key West!
Apartment
Key West, FL, USA
8.5k from Rockland Key center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$362
Average price / night
Check Availability
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
Ibis Bay Resort
Ibis Bay Resort
Resort
Rockland Key, Key West, Florida, USA
9.8k from Rockland Key center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Places to stay

56 Bedrooms24 Guests
7.4

Good

2257 reviews

$427
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
Check Availability
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
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
5.6k from Rockland Key center

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

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$836
Average price / night
Check Availability
Tidelands House at Lunara Bay
Tidelands House at Lunara Bay
House
Key West, FL, 33040, United States
5.6k from Rockland Key center

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

8 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$2997
Average price / night
Check Availability
The Dreamside House at Lunara Bay
The Dreamside House at Lunara Bay
House
Key West, FL, 33040, United States
5.6k from Rockland Key center

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

8 Bedrooms16 Guests
9.6

Exceptional

4 reviews

$2977
Average price / night
Check Availability
The Joyrise House at Solaire Lunara Bay
The Joyrise House at Solaire Lunara Bay
House
Key West, FL, 33040, United States
5.6k from Rockland Key center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$2604
Average price / night
Check Availability
Private & Haven-ly pool home on boating canal
Private & Haven-ly pool home on boating canal
House
Key Haven, FL, 33040, United States
5.7k from Rockland Key center

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

3 Bedrooms9 Guests
New to Booking
$320
Average price / night
Check Availability
Key Haven Coastal Retreat - Canal front with pool
Key Haven Coastal Retreat - Canal front with pool
House
Key Haven, FL, 33040, United States
5.7k from Rockland Key center

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

4 Bedrooms8 Guests
New to Booking
$499
Average price / night
Check Availability
The Sunray Home at Lunara Bay
The Sunray Home at Lunara Bay
House
Key West, FL, 33040, United States
5.7k from Rockland Key center

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

8 Bedrooms16 Guests
10.0

Exceptional

3 reviews

$3035
Average price / night
Check Availability
Evershore Estate at Lunara Bay | Wellness Home
Evershore Estate at Lunara Bay | Wellness Home
House
Key West, FL, 33040, United States
5.7k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms12 Guests
9.8

Exceptional

27 reviews

$1809
Average price / night
Check Availability
Mastway House at Lunara Bay - Wellness Home
Mastway House at Lunara Bay - Wellness Home
House
Key West, FL, 33040, United States
5.7k from Rockland Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms12 Guests
9.6

Exceptional

33 reviews

$1809
Average price / night
Check Availability
**MARINER’S HIDDEN HAVEN @ KEY HAVEN** Waterfront Home & Pool + LAST KEY SERVICE
**MARINER’S HIDDEN HAVEN @ KEY HAVEN** Waterfront Home & Pool + LAST KEY SERVICE
House
Key West, FL, 33040, United States
5.7k from Rockland Key center

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

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$421
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 Oceanfront Rentals in Rockland Key.

Where to stay in Rockland Key? Best neighborhoods & areas

Rockland Key Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 160 verified oceanfront rentals in Rockland Key. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Rockland Key vary depending on the property size, exact beachfront location, and season. Rates typically start from around $196 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Rockland Key offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Rockland Key welcome pets. Currently, 40 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Rockland Key often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.