Rockland Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Rockland Key holiday rentals

Pool

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
9.0 out of 10, Wonderful, (61 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
The price is HK$1,585
HK$3,156 total
includes taxes & fees
21 May - 22 May
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Terrace/patio

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (185 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is HK$1,726
HK$3,491 total
includes taxes & fees
14 May - 15 May
Waterfront Home
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (185 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is HK$1,022
HK$2,462 total
includes taxes & fees
18 May - 19 May
Aqua Lodges at Hurricane Hole Marina
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (98 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
The price is HK$1,585
HK$3,333 total
includes taxes & fees
18 May - 19 May
Canal front, dockage, 2 bedroom, 2 bath
Exterior

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is HK$1,949
HK$4,317 total
includes taxes & fees
20 May - 21 May
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$4,404
HK$8,036 total
includes taxes & fees
21 May - 22 May
Atlantic View Luxury Villa with Pool
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is HK$2,740
HK$5,327 total
includes taxes & fees
18 May - 19 May
Spanish Queen @Venture Out, Cudjoe Key
Marina

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is HK$2,740
HK$5,408 total
includes taxes & fees
3 Jun - 4 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Beach

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
The price is HK$3,171
HK$6,505 total
includes taxes & fees
15 May - 16 May
Old Florida Style, wrap around porch, boat basin for dockage, open water
Outdoor pool

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (37 reviews)
"The location was fabulous, due to the hotel’s amenities. Ie the hourly transport to downtown.pools and restaurants. The accommodations were a bit dated but adequate. The host responded immediately to our request! "
United States
Leigh P.
The price is HK$1,957
HK$3,969 total
includes taxes & fees
21 May - 22 May
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Pool

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is HK$4,521
HK$9,269 total
includes taxes & fees
26 May - 27 May
Private and Exclusive Florida Keys Getaway
Exterior detail

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is HK$1,315
HK$2,849 total
includes taxes & fees
26 May - 27 May
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Outdoor pool

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (68 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is HK$3,906
HK$10,153 total
includes taxes & fees
17 May - 18 May
One of the very few beach houses with a daily, rental license in the Keys.
Marina

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (60 reviews)
"Friendly host and unique location"
United States
Scott
The price is HK$2,505
HK$3,178 total
includes taxes & fees
21 May - 22 May
Living the Dream Key West Style
Terrace/patio

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is HK$2,740
HK$6,762 total
includes taxes & fees
18 May - 19 May
House of the Rising Sun - VO479
Marina

Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (26 reviews)
"Great location!Breeze in the balcony while sitting in chairs or taking a nap in the hammock were amazing!Everything was nearby and easily accessible. Views are wonderful!We had a great time spending holidays as a family. "
United States
PARESH J.
The price is HK$1,730
HK$4,006 total
includes taxes & fees
20 May - 21 May
Waterfront Condo Dock Pool Near Duval St
1 bedroom, WiFi

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (37 reviews)
"Clean place, felt safe and the location was convenient to our vacation activities. Would recommend to others."
United States
Shannon L.
The price is HK$682
HK$2,840 total
includes taxes & fees
28 May - 29 May
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Terrace/patio

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (8 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is HK$3,493
HK$7,179 total
includes taxes & fees
1 Jun - 2 Jun
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Exterior detail

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is HK$1,147
HK$3,241 total
includes taxes & fees
8 Jun - 9 Jun
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Property grounds

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is HK$1,102
HK$3,530 total
includes taxes & fees
14 May - 15 May
The Cat Island Suite | Charmingly Renovated w/ Pool
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Rockland Key Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Great spot in Key West, nice pool and beach, spacious suites and convenient access to area"
Anthony 4-night trip
Posted 1 hour ago
Beachside Resort & Residences

Find out more about Rockland Key

Search for holiday rentals in Rockland Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Rockland Key using one of the methods below:

  • View our selection of featured holiday rentals in Rockland Key
  • Use the map to find apartments and other holiday homes in the Rockland Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Rockland Key while they last

Look no further and take a look at our great range of rental properties in Rockland Key!