Find Extended Stay Hotels in Islamorada, FL

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Top Islamorada Extended Stay Hotels | Reserve now, pay later

The Caribbean Resort
Exterior
The Caribbean Resort
3.5 star property
Pool
Hot Tub
Air conditioning
10.0 out of 10, Exceptional, (134)
    cleanliness
    Cleanliness is scored top 10% in Islamorada by travelers.
"What a wonderful resort in paradise. We stayed in the Bird of Paradise and it was perfect. Look out the window at the Atlantic Ocean. Would definitely come back again. 5 stars. "
The Caribbean Resort
Guarantee Best Sunsets in the Keys!
View from property
Guarantee Best Sunsets in the Keys!
Hot Tub
Kitchen
Washer
10.0 out of 10, Exceptional, (22)
"Love this place. The house was clean and nice. Million dollar view. Would definitely stay here again."
Guarantee Best Sunsets in the Keys!
Mitchells Keys Villa - private, secluded bayfront home
Beach/ocean view
Mitchells Keys Villa - private, secluded bayfront home
Hot Tub
Kitchen
Washer
9.8 out of 10, Exceptional, (56)
"We were more than pleased with our stay! The property is beautiful and our cottage was comfortable, beautiful and ideal for us. Location wise, everything you could need is right there like fabulous eats, Publix, tackle shops, World Wide Sportsman (also easily accessed by boat) as well as some museums and attractions. Our cottage was bigger than it looked and beautifully bright with the practically wrap around windows looking into the gardens. The sunsets were beautiful and the marina well...
Mitchells Keys Villa - private, secluded bayfront home
Angler's Reef Resort by KeysCaribbean
Outdoor pool
Angler's Reef Resort by KeysCaribbean
3.5 star property
Pool
Kitchen
Washer
9.4 out of 10, Exceptional, (12)
"The pool and the beach are incredible. Great place to stay. Great family vacation spot. "
Angler's Reef Resort by KeysCaribbean
Large Screened Porch, Professional Cleaning, Wifi
On the beach
Large Screened Porch, Professional Cleaning, Wifi
Ocean view
Pool
Kitchen
9.4 out of 10, Exceptional, (93)
"We very much enjoyed the condo. We had a beautiful view from our balcony which was very relaxing. The condo and grounds were very well kept. The kitchen was well stocked and the owner provided everything we needed. Jeanette responded immediately to our inquiry. We met some very lovely people during our stay and we are happy we chose the Seagull for our vacation."
Large Screened Porch, Professional Cleaning, Wifi
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Pines & Palms Resort
3.0 star property
On private beach
Pool
Free WiFi
9.2 out of 10, Wonderful, (953)
"This is the cutest hotel in Islamorada that had a little bit of everything! Close to everything, I just wish that they offered some kind of breakfast or coffee! But they do have a full kitchen"
The price is $230
$307 total
includes taxes & fees
Apr 30 - May 1
Pines & Palms Resort
Islander Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
On private beach
Pool
Hot Tub
9.0 out of 10, Wonderful, (1002)
"Beautiful and expansive grounds, nice beach area, two pools and a food/drink spot. Well equipped room was large and clean with microwave, fridge and coffee maker. Close to restaurants and bars. Recommended! "
The price is $258
$346 total
includes taxes & fees
May 5 - May 6
Islander Resort
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor
3.0 star property
Pool
Pet friendly
Parking included
9.0 out of 10, Wonderful, (1000)
"The trailer I stayed in with my wife it needs a better a/c unit"
The price is $186
$244 total
includes taxes & fees
Apr 25 - Apr 26
Drop Anchor
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers
Islander Bayside Villas and Boatslips
3.5 star property
Pool
Parking included
Free WiFi
9.0 out of 10, Wonderful, (335)
"Lovely sister property to the Islander - Resort; the, Islander Bayside resort Townhomes are wonderful. The Green Tuttle Inn. And the NEST across overseas highway great spirits & food. kitchens open until 10pm. 7 am green turtle breakfast. Or Mangrove Mike’s is a short walk North for breakfast. First night we walked to Lorelei, (15 minutes walk) for sunset. Best spot. This property is Slightly less than 2 miles NORTH from Bud and Mary’s marina and Lazy Days. Ideal for family or larger...
The price is $319
$414 total
includes taxes & fees
May 1 - May 2
Islander Bayside Villas and Boatslips
Breezy Palms Resort
Exterior
Breezy Palms Resort
2.5 star property
Pool
Kitchen
Free WiFi
8.4 out of 10, Very Good, (305)
"Fantastic rooms! Amazing beds! Pool right outside our porch! Excellent value. "
The price is $137
$207 total
includes taxes & fees
Apr 28 - Apr 29
Breezy Palms Resort
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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.

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Frequently asked questions

What are the best extended stay hotels in Islamorada?
Islander Resort is one of the 80 long-term rentals available in Islamorada. A swimming pool and a barbecue grill are a sample of the amenities you’ll have access to here. Another excellent option is Pelican Cove Resort & Marina. It offers a picnic area and dry cleaning and laundry services. Whichever getaway you choose, you’ll appreciate the convenience of having a kitchen where you can make your own meals and indulge in a late-night cookie (without anyone knowing). Expedia’s range of long-term hotel stays in Islamorada have a total average guest review rating of 9.2.
What are the best long-term hotels in Islamorada?
If you’re thinking about an extended stay in Islamorada, you’ll need someplace packed with awesome amenities. One of our favorites? The Caribbean Resort Royal Palm South. It comes with a swimming pool, a barbecue grill and a kitchen where you can prepare your favorite meals. Another long-term hotel to look into is The Caribbean Resort Malayan Palm North. With conveniences such as a barbecue grill, an ATM machine and cooking facilities, a stay here is nice and easy.
Are there any cheap extended stay hotels in Islamorada?
With extended stay hotels in Islamorada starting from just $137 per night, you’re sure to score one at an ideal price.* Check out Pines & Palms Resort. This budget getaway comes with many nearby restaurants and a swimming pool and is about 3.0 mi from downtown. Another popular pick is Lookout Lodge Resort, 5.0 mi from the center. Spend your extended stay in Islamorada here and enjoy the use of conveniences like a barbecue grill and a convenience store.You’ll find tons of awesome free attractions around Islamorada if you need to sightsee cheaply too. Bud n’ Mary’s Dive Center and Islamorada County Park are just a small slice of what’s on offer.*These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best weekly hotel rentals in Islamorada?
Whether you’re on the lookout for long-term hotels with weekly rates or a place to stay overnight, you’ll find your perfect pad on Expedia. Planning to stick around a while in Islamorada? Do it from Waterfront/tropical Landscaped Home With Magnificent Gulf View. Enjoy amenities designed for longer stays here, such as a kitchen, a nearby laundromat and a nearby coin laundry. Also consider Breezy Beach Waterfront Home In Port Antigua. There’s a lot to love about this option, from an oven to a washing machine. For a little more travel inspo, don’t miss Expedia’s One-week Vacations & Getaways. Book one of our featured 7-day deals or create your own!
What are the top pet-friendly extended stay hotels in Islamorada?
There’s no need to leave your best bud at a pet resort during your extended stay in Islamorada. One place that’ll greet you and your pooch with open paws is Immaculate Oceanfront Villa With Resort Amenities. It has a host of amenities that cater to both furry and human guests, including pet-friendly services and a patio. Your pup can also be part of the fun at Gorgeous 3/2 Plus Loft Islamorada Next To Marina. Plan a long-term stay in a pet-friendly room and take advantage of this hotel’s conveniences, including pet-friendly services and a garden.
What's the best extended stay hotel in downtown Islamorada?
Sample the vibe and culture of Islamorada from The Caribbean Resort Royal Palm South. With a central location and amenities such as an ATM machine and a swimming pool, it’s a popular choice among travelers planning to stick around a while. The Caribbean Resort Royal Palm North will also place you near all the action. This extended stay hotel offers an ATM machine, a barbecue grill and more. As that old ‘60s song goes — everything’s waiting for you downtown! Theater of the Sea and Bud n’ Mary’s Dive Center are two attractions within easy reach of Islamorada’s center when it’s time to go out and explore.
What are the best extended stay hotels with kitchens in Islamorada?
If you’re taking a trip with the kids, eating out doesn’t need to swallow a large chunk of your travel budget. Save on takeout bills at The Caribbean Resort Malayan Palm North. Featuring a kitchen, a nearby beach and cycling, this hotel is ideal for families. You can also cater to rumbling stomachs at The Caribbean Resort Royal Palm South. A swimming pool and a nearby beach make this option one of the most popular long-term stays in Islamorada.
Can I find extended stay hotels with pools in Islamorada?
Whether you’re the sort of person who wants to cannonball in or just lazily float around, a pool is a fantastic addition to any vacation. Create memories with your family at Immaculate Oceanfront Villa With Resort Amenities. This extended stay in Islamorada also has an oven and fitness facilities. After a busy day of sightseeing, put your feet up poolside at The Caribbean Resort. This is another popular long-term stay that offers a barbecue grill and free internet services.Anytime is a good time to be in Islamorada, which has a tropical savanna climate. But if you’d love to spend your escape in the water, visit in the summer months when temperatures range between 82 ºF and 84 ºF.
What are the top extended stay hotels with 2 bedrooms in Islamorada?
Gated Waterfront Community With Marina is an excellent choice for small groups or families. Featuring two bedrooms, a patio and a swimming pool, you’ll be comfortable here during your extended visit to Islamorada. Alternatively, spend your getaway at Beautiful Sunlit Home With Shared Pool And Tennis Court. This popular two-bedroom option also has conveniences that are suited to long-term stays, such as a kitchen, a patio and a swimming pool.
Why book an extended stay hotel in Islamorada through Expedia?
If you’re after a long-term rental for your extended stay in Islamorada, Expedia’s got you covered. Simply filter your results by price, rating and location to narrow down your perfect long-term stay. Some of these terrific properties may even offer weekly rates. Want to snag the best deals? Sign up to become an Expedia member for free and save a ton of cash with special offers — plus you’ll receive reward points on every booking. Our extended stay hotels in Islamorada have amenities like laundries and kitchens, so even though you’re far away, you can still experience the comforts of home.
What can I expect from an extended stay hotel?
Featuring amenities such as kitchens, laundries and dining areas, extended stay hotels in Islamorada can be a convenient and cheaper alternative to your standard property. Make home-cooked meals and avoid laundromat bills. Sometimes offering discounted weekly rates, extended stay hotels range from simple studios to luxurious and large options with two or more bedrooms. They also have many of the amenities you’d expect in a standard hotel, like recreational facilities or 24/7 guest services. If you want flexibility, privacy and the comforts of home for a few weeks or more, an extended stay hotel is an ideal choice.

Recent reviews of Islamorada hotels
Expedia verified reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
Great stay!
"It was a one night stay on my way to Key West with my brothers. Room was great and we even were able to check in early. Close enough to walk to a couple restaurants and bars, so after spending the afternoon looking around we were able to park the car and enjoy the evening on the water."
A verified traveler stayed at Chesapeake Beach Resort
Posted 8 hours ago
Chesapeake Beach Resort

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