A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Rentals

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Our top choices for Islamorada vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (762 reviews)
The price is CA $150
CA $192 total
includes taxes & fees
Oct 21 - Oct 22
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (177 reviews)
"Beautiful unique place"
United States
Laura
The price is CA $152
CA $371 total
includes taxes & fees
Oct 10 - Oct 11
Treasure Harbor

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (41 reviews)
The price is CA $152
CA $482 total
includes taxes & fees
Nov 3 - Nov 4
Florida Keys Getaway - Slps 4 - Ocean View

4. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
The price is CA $178
CA $510 total
includes taxes & fees
Oct 13 - Oct 14
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

5. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is CA $220
CA $608 total
includes taxes & fees
Oct 13 - Oct 14
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

6. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $192
CA $532 total
includes taxes & fees
Nov 1 - Nov 2
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

7. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is CA $198
CA $749 total
includes taxes & fees
Oct 18 - Oct 19
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

8. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is CA $192
CA $497 total
includes taxes & fees
Oct 12 - Oct 13
Amazing Ocean view condo

9. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is CA $258
CA $665 total
includes taxes & fees
Oct 12 - Oct 13
3212 Across from Pool * King & Queen/Twin Bunk Bed

10. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
The price is CA $271
CA $341 total
includes taxes & fees
Oct 18 - Oct 19
2BR Oceanfront Suite w/ Beach & Marina Access

11. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Very cute cozy house boat. Well equipped and close to restaurant. Enjoyable weekend stay. Heidi the host is very welcoming."
United States
Michelle P.
The price is CA $352
CA $627 total
includes taxes & fees
Oct 11 - Oct 12
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

12. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (19 reviews)
"Great stay"
United States
Blain R.
The price is CA $213
CA $598 total
includes taxes & fees
Oct 13 - Oct 14
Sunrise Sanctuary - Top Floor Ocean Pointe 2415

13. Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is CA $243
CA $638 total
includes taxes & fees
Oct 13 - Oct 14
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

14. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is CA $253
CA $575 total
includes taxes & fees
Oct 11 - Oct 12
Ocean view condo with balcony/marina view

15. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is CA $244
CA $645 total
includes taxes & fees
Oct 16 - Oct 17
Lazy Daze Double King Suite Ocean Pointe 2310

16. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
The price is CA $269
CA $492 total
includes taxes & fees
Oct 18 - Oct 19
Ocean Pointe Ocean View w/heated pool beach marina

17. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
The price is CA $229
CA $625 total
includes taxes & fees
Oct 11 - Oct 12
Marina to Ocean View Key Largo Ocean Pointe 5308

18. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is CA $141
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

19. Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201

Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
Tavernier
10.0 out of 10, Exceptional, (1 review)
"This was a great unit for our purpose. Felt newly remodeled. Beds were comfy. Nice extras provided, like a cooler, pool noodles, pickleball, tennis rackets and some fishing gear. Check in & out was one of the easiest, so far. The pool was a HUGE hit. Location was good. Close to the park and good food. Husband only wished we were a bit closer to fishing, but we just didn’t know. Only critiques; wish the couch was a bit bigger. It isn’t bad, just a note. And the patio is small and the furniture...
United States
Cara B.
The price is CA $251
CA $648 total
includes taxes & fees
Oct 13 - Oct 14
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201

20. Key Largo Baha Penthouse Ocean Pointe 1416

Key Largo Baha Penthouse Ocean Pointe 1416
Tavernier
9.8 out of 10, Exceptional, (28 reviews)
"Very nice penthouse and enjoyed our visit"
United States
Allen
The price is CA $220
CA $614 total
includes taxes & fees
Nov 9 - Nov 10
Key Largo Baha Penthouse Ocean Pointe 1416
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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Top Islamorada Hotel Reviews

Find out more about Islamorada

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Islamorada. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation home rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 403 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Anne's Beach and Fiesta Key are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. Other places in town to visit include Bud n' Mary's Dive Center and Robbie’s of Islamorada.

What’s a vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.