Villa holiday rentals in Islamorada

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Popular amenities for Islamorada villa rentals

Private villa rentals

Villa in Islamorada
5 out of 5 average rating, 3 reviews

The Nest Villa & Marina in the heart of Islamorada

JoanneRating, 5 stars1 week ago
This was our second stay at The Nest and we will be back! The interior is so soothing, comfortable, clean and very well stocked. Communication with the host was great and they were very responsive to questions. The surroundings are beautiful and peaceful, and the HUGE patio was so perfect for relaxing at the end of the day. Can’t wait to go back!
Superhost
Villa in Duck Key
4.83 out of 5 average rating, 78 reviews

Villa 5034 on Duck Key BOAT SLIP available

MeganRating, 5 stars3 months ago
Frank's place was just as listing shows! Perfect location on Duck Key. Beautiful sunsets right on Tom's Harbour. Would recommend to others!
Villa in Marathon
4.76 out of 5 average rating, 153 reviews

Sunset Villa in Duck Key

HeatherRating, 5 stars1 week ago
It was one of cleanliness Villas I have stayed in . We have been vacationing on Duck Key for 20 plus years and would definitely recommend 5085 - great location , very reasonable price and very simple easy check in and check out instructions. Thank you .
Villa in Duck Key
4.81 out of 5 average rating, 107 reviews

Waterfront villa for families * Family friendly*

MarcRating, 5 stars2 weeks ago
The resort is well taken care of and the amenities provided definitely made you feel at home! The area was surrounded by beautiful scenery, wildlife, and right on the water. The best part was the convenient location that was in the mix of several activities, restaurants, and local attractions!
Superhost
Villa in Duck Key
4.91 out of 5 average rating, 47 reviews

Villa 5028 on Duck Key BOAT SLIP available

EdwardRating, 5 stars2 months ago
This is a great spot. Very quiet and close to everything we wanted to do. The place was spotless and had everything we needed. Frank is very responsive. I highly recommend this place.
Villa in Marathon
4.56 out of 5 average rating, 16 reviews

Key Lime Cottage - Lovely Duck Key Villa, Dip Pool

DelphineRating, 5 stars1 week ago
Tina's place was beautiful and very comfortable. It was exactly as described and had everything we needed. The dip pool was so enjoyable throughout the day! The view of the canal was nice to enjoy while eating on the back patio. Highly recommend and would definitely look for availability for future travels to the Keys! Thank you Tina!
Superhost
Villa in Marathon
4.86 out of 5 average rating, 97 reviews

Villa 5023 on Duck Key BOAT SLIP available

AndreiRating, 5 stars3 weeks ago
Great spot! Everything was as described. Clean, well located, quiet. Would gladly stay again.
Villa in Duck Key
5 out of 5 average rating, 3 reviews

Crystal Waters - 2/2.5 Villa

JuanRating, 5 stars3 weeks ago
Words do not explain the value of this villa. We stayed 4 days which clearly wasnt enough! Im incredibly content with how Joe, Merri, and Ana treated us during this trip. Also, the villa was actually better in person. Thank you for everything! We're already planning our next stay here.

Luxury villa rentals

Villa in Key Largo
5 out of 5 average rating, 10 reviews

Spring Break Getaway: Villa w/ Marriott Amenities

VictoriaRating, 5 stars5 days ago
Place as described. Host was fast to respond to any issues. The only thing I would love to have in instructions is the number of the unit - we where provided with the name and the house did not have the name anywhere - just the number.
Guest favourite
Villa in Islamorada
5 out of 5 average rating, 35 reviews

Anglers Reef Islamorada

KatherineRating, 5 stars1 month ago
What a great place to stay! The community was well kept and the amenities were wonderful. There are great restaurants close by and it's location is perfect. We had a wonderful time and met some really wonderful people. We plan on returning, next year!
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Bayberry Key: FREE Boat Dockage Sep-Oct Only!

PeterRating, 5 stars4 months ago
Great place, there are many bars, restaurants, stores and art galleries to walk to. The pool area is great. We rented kayaks and paddled every day.
Guest favourite
Villa in Marathon
4.88 out of 5 average rating, 59 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!
Guest favourite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

KatrinRating, 5 stars2 months ago
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!
Villa in Marathon
4.8 out of 5 average rating, 25 reviews

"Casa Azul Villa" Oceanfront-Marathon-8Guests-Dock

EdithRating, 5 stars4 months ago
This place was decorated beautifully! Very unique furnishings and decorations were fun! Outside area was beautiful. Spent every day there! Sunsets from the end of the dock were beautiful! The landscaping was spot on, even some orchids in the trees! Loved the colorful dishes and modern appliances, and the coffee pods were awesome! I am getting the same machine now! Privacy and quiet neighborhood is hard to find in some areas of the keys. Walked several days on the street. Nice towels, beach towels and comfortable sheets, pillows and throws. My husband loved the fake fur one in the LR! Thank you for the lovely stay!
Villa in Islamorada
4.75 out of 5 average rating, 8 reviews

Scenic Resort w/ Outdoor Pool | Florida Keys Stay

KevinRating, 5 stars2 weeks ago
Don’t tell anybody about my spot lol! I’m definitely coming back over and over. This place is so much more than advertised and a great family friendly experience!
Guest favourite
Villa in Marathon
4.9 out of 5 average rating, 39 reviews

Discount Available! 4BR 3BA! So Many Amenities!

AngelaRating, 5 stars3 weeks ago
Great family vacation spot. Spacious house, great outside area especially with the added tiki hut area. We got to use the beach toys and beach chairs, the paddle boards and the pool floats. House looks just like the pictures. Well maintained, great furniture and clean! Excellent location too! 1.5 miles from Sombrero Beach, Publix 1 mile down the road.

Villa rentals with a pool

Villa in Duck Key
4.38 out of 5 average rating, 21 reviews

2BR water view with private pool, balcony & kayak

StefanieRating, 5 stars3 months ago
We overall had an amazing stay! Beautiful views, clean house, & responsive hosts!
Villa in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars30 months ago
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.
Top Guest favourite
Villa in Marathon
5 out of 5 average rating, 22 reviews

Indigo Reef water view Villa- #1 Guest Favorite

MarthaRating, 5 stars1 month ago
Perfect location in the Middle Keys with easy access to all that Marathon has to offer, Key West or Islamadora. The home is well appointed and the views of the Gulf out the two back porches are spectacular! Very peaceful setting and close to the docks and pool. Would stay here again in a heartbeat!
Villa in Key Largo
5 out of 5 average rating, 3 reviews

Dolphin 1-Bedroom Villa

KellyRating, 5 stars39 months ago
A beautiful quiet place to stay. Kayaking in the morning and swimming in the pool at night. We loved exploring other Florida Keys and coming back to sleep. Easy check in and out.
Villa in Duck Key
5 out of 5 average rating, 5 reviews

Florida Keys Sanctuary

ChristopherRating, 5 stars6 days ago
Our Adventure and Family Vacation With This Beautiful Home was an amazing experience! It was a beautiful space that felt very comfortable and warm. We had family and friends staying with us during our say so, this home provided a different feel and look to the rooms that was versatile in providing options for our guests that suited there needs. The beds were beyond comfortable and kitchen was just the right size to host us. It was the different feel we needed especially when it came to the amenities offered. We didn't hear any complaints from neighbors during our stay and I was getting all the praise from the Wife for finding such a real great place for her Birthday Party / Fathers Day Get Away - It was a True Diamond ! We will look to book in the future!
Villa in Marathon

Luxury Waterfront Villa, Marathon, Florida Keys

ShawnRating, 5 stars5 months ago
Very clean quiet and an excellent pool area!
Villa in Key Largo
4.79 out of 5 average rating, 68 reviews

Oceanfront Villa overlooking the Atlantic

ShannonRating, 5 stars27 months ago
My family really enjoyed our stay at Vivian’s place! The photos do not do it justice! Very roomy, amazing water views, and beautiful decor/upgrades. Vivian had everything we needed for our stay - we traveled with a toddler and baby and everything we needed was there. Vivian was responsive and helpful. We would definitely stay again! Thanks Vivian!
Villa in Key Largo
4.85 out of 5 average rating, 47 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

JosmelyRating, 5 stars1 week ago
We had a great time at Paul's place. Fully equipped home and close to all places we wanted to go. The complex has many amenities great for families including a lagoon right in front of the condo. We used the marina given that we brought our boat to do snorkeling, everything went well with this as well. Paul was flexible with us and was available when we had questions. We would come again!

Quick stats about villa rentals in Islamorada

  • Total rentals

    50 properties

  • Nightly prices starting at

    $486 NZD before taxes and fees

  • Total number of reviews

    340 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
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