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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Islamorada and around

The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is €577
includes taxes & fees
14 Aug - 15 Aug
The Islands of Islamorada
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
On the beach, sun-loungers, beach towels

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (115)
"The property and the location was absolutely perfect. "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
Marina

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (51)
"Great location Vivian was very responsive to any questions we had"
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
2bd/2ba Ocean Retreat in Kawama Yacht Club
Sun-loungers

2bd/2ba Ocean Retreat in Kawama Yacht Club

10.0 out of 10, Exceptional, (43)
"We enjoy the property and great Key Largo location. Owner was very quick to respond to questions. Some repairs are needed that he is aware of and he said they would be fixed soon. "
2bd/2ba Ocean Retreat in Kawama Yacht Club
Newly upgraded Key Largo Villa W/Boat Slip
A heated pool

Newly upgraded Key Largo Villa W/Boat Slip

10.0 out of 10, Exceptional, (81)
"Excellent location Great value"
Newly upgraded Key Largo Villa W/Boat Slip
Waterfront House with Boat Dock
Terrace/patio

Waterfront House with Boat Dock

5.0 star property
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
Waterfront House with Boat Dock
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Outdoor pool, a heated pool

Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

10.0 out of 10, Exceptional, (13)
"Anglers Way was a meticulously clean property centrally located on Islamorada. The hosts were extremely responsive to our inquiries prior to and during our stay in their home. The property was well equipped and provided for all our needs. They undoubtedly deserve our 5 star review and would recommend this property for those seeking a restful vacation. "
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Pool

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

9.4 out of 10, Exceptional, (3)
"We’ve vacationed in the Keys many times and this property was the best. First is location. It’s on a canal cut off Little Basin. There are many walkable restaurants and attractions. The house itself was very clean and the layout conducive to renters with two master suites upstairs and a smaller bedroom and bath down. Property management very attentive and communicative with a very nice young lady coming on site. Beautiful pool area and deck by water. Can’t go wrong with this."
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Exterior

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

10.0 out of 10, Exceptional, (2)
"The house is clean, well decorated, and equipped with everything that you would need for a vacation. Quick response and good communication. The plunging pool was great at the house, and a larger pool - ocean side if you need more sun! Within walking distance to restaurants, and Cafe Moka next door. We would stay here again, in a heart beat."
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only
A heated pool

Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only

3.0 star property
10.0 out of 10, Exceptional, (4)
"The home was just as it was described on the website! Beautiful, comfortable and clean. Plenty of cooking items. Location was wonderful-we could walk to several restaurants and store. Would stay again!"
Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
A heated pool

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

10.0 out of 10, Exceptional, (1)
"This was a beautiful spot for 3 couples to relax and enjoy this beautiful setting. The outside space was perfect with tables, firepit & grills. The house was stocked well enough to be able to prepare some meals. I would definitely return again."
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
A heated pool

Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only

10.0 out of 10, Exceptional, (2)
"Fantastic location with loads of bars and restaurants within walking distance. Property is lovely, very clean and modern with a great pool. Definitely stay again."
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
Property grounds

Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**

10.0 out of 10, Exceptional, (24)
"What a wonderful place to stay from getting to meet Ryan and enjoy all of the amenities. The thoughtfulness of key lime pie and other local specialties, kayaks, paddle boards, corn hole, bait bucket and fishing rods, and more. The outdoor seating was plentiful and the views are amazing!! We highly recommend enjoying this property."
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Exterior

Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

10.0 out of 10, Exceptional, (3)
"This place is a gem!!"
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
A heated pool

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Pool

Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Marina

Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.

10.0 out of 10, Exceptional, (90)
"Excellent place to get away and enjoy the key’s lifestyle"
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
A heated pool

Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

10.0 out of 10, Exceptional, (3)
"We had a wonderful time and the property was perfect!"
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
Marina

The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets

9.4 out of 10, Exceptional, (3)
"The house was perfect for our family. We loved the layout and the pool in the back was perfect after a day on the water. Great location to everything in Islamorada. Hope to be back again soon."
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Property grounds

Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.

9.8 out of 10, Exceptional, (39)
"Lloyd's place is outstanding in every way! You can't go wrong staying here, from the location to cleanliness to exceptional service from Lloyd! We have already planned three more trips and look forward to our next trip!"
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Been coming to the keys for 29 years, absolutely the best place we have ever stayed. Staff, rooms, food were second to none. "
Anthony 1-night trip
Posted 2 days ago
Cheeca Lodge & Spa

Frequently asked questions

How much do villas in Islamorada cost?
Prices for villas in Islamorada range between €577 and €577 per night. Whatever your budget, you'll find a place that fits the bill on Expedia. 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.
How many villas are there in Islamorada?
Choose from 46 villas in Islamorada. Whether you're taking a trip with the family or planning a getaway with some friends, Expedia can help you find the perfect space for your whole crew.
Are there any family-friendly villas in Islamorada?
If you're on your way to Islamorada and searching for a family-friendly villa, you can't pass up Anglers Reef Villa 1. This 3.5-star stay features amenities like a barbecue grill and an oven. After checking in and chilling together in your cosy digs, it's time to hit the road and discover some of the local sights. Theatre of the Sea and Anne's Beach are just two family-friendly attractions in Islamorada.