Monroe County Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Top cities in Monroe County

Islamorada featuring a beach and tropical scenes
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Islamorada

Islamorada
South Beach featuring tropical scenes, general coastal views and a beach
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Key West

Key West
Marathon featuring tropical scenes, a sandy beach and swimming
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Marathon

Marathon

Monroe County Vacation Rentals

Skipjack Resort & Marina

Skipjack Resort & Marina

3 out of 5
19 Sombrero Blvd Marathon FL
Free Cancellation
Reserve now, pay when you stay
$316 nightly
The price is $356 total per night
$356 total
Apr 5 - Apr 6
Total with taxes and fees
Skipjack Resort & Marina features a marina, an outdoor pool, and a gym. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and securing valuables. Other amenities at this golf aparthotel include meeting rooms, a business center, and a computer station.
Pool
Kitchen
Yacht Haven Marina

Yacht Haven Marina

3.5 out of 5
5 Sombrero Blvd Marathon FL
$394 nightly
The price is $443 total per night
$443 total
Mar 10 - Mar 11
Total with taxes and fees
Yacht Haven Marina features free WiFi in public areas and a picnic area. You can take advantage of free parking if you drive. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This houseboat also has barbecue grills.
Kitchen
Pet friendly
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
$304 nightly
The price is $342 total per night
$342 total
Mar 9 - Mar 10
Total with taxes and fees
Guests staying at Treasure Harbor enjoy an outdoor pool, free WiFi in public areas, and a vending machine. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area.
Pool
Parking included
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
$314 nightly
The price is $353 total per night
$353 total
Apr 1 - Apr 2
Total with taxes and fees
Guests staying at Old Wooden Bridge Resort and Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. If you plan to drive, free parking is available. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include express check-in, a terrace, and barbecue grills.
Pool
Pet friendly
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$241 nightly
The price is $271 total per night
$271 total
Mar 25 - Mar 26
Total with taxes and fees
Guests staying at Breezy Palms Resort enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Self parking is available for USD 30.00 per day. Helpful staff can provide tour or ticket assistance, luggage storage, and a safe deposit box at the front desk. Other amenities at this beach aparthotel include a terrace, laundry facilities, and a gift shop.
Pool
Kitchen
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf Marathon FL
$230 nightly
The price is $259 total per night
$259 total
Mar 10 - Mar 11
Total with taxes and fees
Tropical Cottages offers a garden, a picnic area, and barbecue grills. If you drive, put free parking to good use. Multilingual staff is on hand to answer questions.
Parking included
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
$346 nightly
The price is $389 total per night
$389 total
Mar 15 - Mar 16
Total with taxes and fees
Guests staying at this houseboat enjoy features like a marina and free WiFi in public areas. You can put free parking to good use if you drive.
Parking included
Free WiFi
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Key West FL
Guests of this cottage have access to free WiFi in public areas.
Kitchen
Washer
Cabins at Bonefish Bay

Cabins at Bonefish Bay

3 out of 5
12565 Overseas Hwy Marathon FL
Guests of Cabins at Bonefish Bay enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. If you plan to drive, free parking is available. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Additional amenities include laundry facilities, a picnic area, and barbecue grills.
Pool
Kitchen
Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club

3 out of 5
107800 Overseas Hwy Key Largo FL
$250 nightly
The price is $281 total per night
$281 total
Mar 8 - Mar 9
Total with taxes and fees
Guests staying at this aparthotel enjoy access to a marina, an outdoor pool, and free WiFi in public areas. If you decide to drive, there's free parking. Front-desk staff can assist with concierge services and securing valuables. Additional amenities include an outdoor tennis court, a library, and a terrace.
Pool
Kitchen
Knight's Key Suites

Knight's Key Suites

3 out of 5
40 Kyle Way W Marathon FL
$224 nightly
The price is $249 total per night
$249 total
Apr 5 - Apr 6
Total with taxes and fees
Guests staying at Knight's Key Suites enjoy an outdoor pool, free WiFi in public areas, and a picnic area. If you drive, put free parking to good use. This aparthotel also has barbecue grills.
Pool
Parking included
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
$848 nightly
The price is $954 total per night
$954 total
Apr 7 - Apr 8
Total with taxes and fees
Guests of The Islands of Islamorada have access to a marina, 2 outdoor pools, and a 24-hour gym. There's free parking if you drive. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this beach villa include free WiFi in public areas, a hot tub, and free use of bicycles.
Pool
Hot Tub
Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

Key West FL
$339 nightly
The price is $376 total per night
$376 total
Mar 16 - Mar 17
Total with taxes and fees
At this apartment, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

Marathon FL
Guests staying at this villa enjoy access to a marina, an outdoor pool, and a hot tub. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,

KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,

Marathon FL
Guests staying at this villa enjoy access to a marina, an outdoor pool, and a hot tub. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.
Pool
Hot Tub
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
2 outdoor pools, free WiFi in public areas, and a hot tub are featured at Coconut Mallory Resort And Marina By Kees Vacations. If you plan to drive, free parking is available. Multilingual staff is on hand to answer questions. Additional amenities include barbecue grills and a picnic area.
Pool
Hot Tub
Key Largo Cottages

Key Largo Cottages

2.5 out of 5
99306 Overseas Highway Key Largo FL
Key Largo Cottages offers a private beach, free use of bicycles, and express check-in. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this beach apartment building include a terrace, barbecue grills, and a garden.
Kitchen
Pet friendly
Charming and Cozy ,2/2 in Key Largo,Where Island Vibes and Adventures Await You.

Charming and Cozy ,2/2 in Key Largo,Where Island Vibes and Adventures Await You.

Key Largo FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Monroe County
View all properties
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.

Hotel Options in Monroe County

    Southernmost Beach Resort and Guesthouses

    Southernmost Beach Resort and Guesthouses

    1319 Duval Street Key West FL
    $495 nightly
    The price is $557 total per night from Apr 5 to Apr 6
    $557 total
    Apr 5 - Apr 6
    Total with taxes and fees
    8.8/10 Excellent! (3,121 reviews)
    Beachside Resort & Residences

    Beachside Resort & Residences

    3841 N Roosevelt Blvd Key West FL
    $366 nightly
    The price is $412 total per night from Mar 8 to Mar 9
    $412 total
    Mar 8 - Mar 9
    Total with taxes and fees
    8.6/10 Excellent! (2,052 reviews)
    Ibis Bay Beach Resort

    Ibis Bay Beach Resort

    3101 N. Roosevelt Blvd Key West FL
    $422 nightly
    The price is $475 total per night from Mar 8 to Mar 9
    $475 total
    Mar 8 - Mar 9
    Total with taxes and fees
    8/10 Very Good! (2,134 reviews)

Orbitz makes it easy to find vacation rentals in Monroe County 

🏠 What is the best price for a Monroe County vacation rental?


Monroe County rentals range between $249 and $954 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Monroe County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Monroe County getaway. Orbitz filters your search results so you can find the best Monroe County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Monroe County vacation rentals with Orbitz?


You may be able to cancel or amend your Monroe County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Monroe County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Monroe County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Monroe County?


When you book a Monroe County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Monroe County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Monroe County—with plenty of hidden gems. We also have plenty of inventory in Monroe County main cities and near popular attraction spots.


🏠 Why should I book my Monroe County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Monroe County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


More to Explore