Monroe County Vacation Rentals

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Top cities in Monroe County

South Beach featuring tropical scenes, general coastal views and a beach
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Key West

Key West

Monroe County Vacation Rentals

Yacht Haven Marina

Yacht Haven Marina

3.5 out of 5
5 Sombrero Blvd, Marathon, FL
$244 nightly
The price is $275 total per night
$275 total
Aug 25 - Aug 26
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
Parking included
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $148 total per night
$148 total
Sep 10 - Sep 11
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 picnic area.
Pool
Kitchen
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
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
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 a picnic area.
Pool
Pet friendly
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf, Marathon, FL
$80 nightly
The price is $90 total per night
$90 total
Aug 24 - Aug 25
Total with taxes and fees
Tropical Cottages offers a picnic area, a garden, and barbecue grills. If you drive, put free parking to good use. Multilingual staff is on hand to answer questions.
Parking included
Restaurant
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr, Islamorada, FL
$215 nightly
The price is $242 total per night
$242 total
Sep 2 - Sep 3
Total with taxes and fees
Treasure Harbor features 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.
Parking included
Free WiFi
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy, Key West, FL
$211 nightly
The price is $238 total per night
$238 total
Aug 24 - Aug 25
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
Skipjack Resort & Marina

Skipjack Resort & Marina

3 out of 5
19 Sombrero Blvd, Marathon, FL
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $219 total per night
$219 total
Sep 1 - Sep 2
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 securing valuables, luggage storage, and tours or tickets. Other amenities at this golf aparthotel include meeting rooms, a business center, and a computer station.
Pool
Kitchen
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane, Key West, FL
Free Cancellation
$272 nightly
The price is $307 total per night
$307 total
Aug 28 - Aug 29
Total with taxes and fees
An outdoor pool and free WiFi in public areas are features at Hyatt Vacation Club at Sunset Harbor, Key West. Self parking is available for USD 35 per night. Front-desk staff can help with concierge services, and provide local restaurant recommendations.
Pool
Free WiFi
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
$599 nightly
The price is $674 total per night
$674 total
Aug 22 - Aug 23
Total with taxes and fees
Guests staying at The Islands of Islamorada enjoy access to 2 outdoor pools, a 24-hour gym, and free WiFi in public areas. 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 a hot tub, barbecue grills, and wedding services.
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 concierge services, and provide local restaurant recommendations. Other amenities at this beach apartment building include a terrace, barbecue grills, and a garden.
Kitchen
Pet friendly
Knight's Key Suites

Knight's Key Suites

3 out of 5
40 Kyle Way W, Marathon, FL
$92 nightly
The price is $100 total per night
$100 total
Sep 8 - Sep 9
Total with taxes and fees
Guests staying at Knight's Key Suites enjoy an outdoor pool, free WiFi in public areas, and barbecue grills. If you drive, put free parking to good use. This aparthotel also has a picnic area.
Pool
Parking included
The Hammocks at Marathon

The Hammocks at Marathon

2.5 out of 5
1688 Overseas Hwy, Marathon, FL
At The Hammocks at Marathon, guests enjoy a marina, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a hot tub, coffee/tea in a common area, and laundry facilities.
Pool
Hot Tub
Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

$205 nightly
The price is $228 total per night
$228 total
Sep 4 - Sep 5
Total with taxes and fees
Guests of this apartment enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free apartment building also has barbecue grills.
Pool
Hot Tub
Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside

3 out of 5
1 47th Street Gulf, Marathon, FL
Aqua Lodges at 47th Street Gulfside features free WiFi in public areas and a picnic area. If you drive, put free parking to good use. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. This houseboat also has barbecue grills.
Parking included
Free WiFi
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

$202 nightly
The price is $224 total per night
$224 total
Aug 24 - Aug 25
Total with taxes and fees
Friendly staff can provide concierge services, and also offer advice about sightseeing.
Pool
Free WiFi
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

At this cottage, guests have access to free WiFi in public areas and laundry facilities.
Kitchen
Washer
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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.

Hotel Options in Monroe County

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $173 nightly
    The price is $194 total per night from Aug 24 to Aug 25
    $194 total
    Aug 24 - Aug 25
    Total with taxes and fees
    9/10 Wonderful! (1,501 reviews)
    Beachside Resort & Residences

    Beachside Resort & Residences

    3841 N Roosevelt Blvd, Key West, FL
    $184 nightly
    The price is $207 total per night from Aug 25 to Aug 26
    $207 total
    Aug 25 - Aug 26
    Total with taxes and fees
    8.4/10 Very Good! (1,468 reviews)
    Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3850 N Roosevelt Blvd, Key West, FL
    $126 nightly
    The price is $142 total per night from Aug 27 to Aug 28
    $142 total
    Aug 27 - Aug 28
    Total with taxes and fees
    7.8/10 Good! (1,069 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 $90 and $674 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. 


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