Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada and around

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (183)
"We greatly enjoyed our stay. The Kawama Property was beautiful. My entire family enjoyed the stay. Many enjoyable things to do on the property. The townhouse was lovely and decorated as pictured in the photos."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (46)
"We stayed a week in the wonderful resort at Kawama. The lagoon was right in front of our unit. There were beautiful tropical fish in the lagoon as well as tarpons and lobster! The 2 pools were heated and delightful to swim in. We love walking out to the end of the jetty each evening to watch the sunset. It was a fantastic place to spend a week and soak up the sun."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (89)
"We were fortunate to get just one day of rain, and otherwise had wonderful weather, which was great because the outdoor space at this property is wonderful. There is a large area to play soccer or throw a ball, as well as beach, long and low dock, and kayaks to use. The outside space is truly what makes this house special. The location is very good and easy to get to -- you're just a handful of miles from some of the more touristy things in Islamorada, making this a quiet spot that still has...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 star property
10.0 out of 10, Exceptional, (4)
"We had such a fun and relaxing time. Swam laps everyday in the beautiful pool. 4 of us each had our own bedroom and bathroom. Excellent location to enjoy the keys. Came home to winter very refreshed. The owner was very helpful with suggestions to explore the keys."
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (10)
"Our group was looking for a warm spot to relax and this place delivered! We had quite a few of us, so it was great to have many places to sleep and lots of living space. Mariner's Club was a beautiful spot and the pools were a beautiful place to spend relaxing days. We had no problem finding great restaurants nearby using Erick's recommendations. "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

8.8 out of 10, Excellent, (10)
"Great location with access to Gulf and Atlantic (a short ride away). Super clean and exactly as advertised. No disappointments. Hosts very responsive to inquiries."
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (19)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

10.0 out of 10, Exceptional, (2)
"All was great we had what we needed and more it was very clean and our host communicated well. We had lots of fun and this house facilitated that!"
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

10.0 out of 10, Exceptional, (4)
"Property was beautiful and perfectly fit our needs for our business fishing trip! "
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (10)
"We stayed at this home during the time between Christmas and New Years (me, my husband and our two teenage children). The house is nice but, be aware it is small. We had a day with rain and with everyone being in the house it just felt cramped. When we arrived the toilet was running constantly. We had to take the top off of the toilet and fix it every time we used the restroom until a repairman came the following afternoon to fix it. If you are traveling to the area during this time of...
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

9.6 out of 10, Exceptional, (127)
"Clean, great location, plenty of room,"
The price is €835
includes taxes & fees
24 Feb - 25 Feb
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Overlooking the Lagoon and Pool Includes Use of Golf Cart & 2 Kayaks

10.0 out of 10, Exceptional, (21)
"The host was very easy to work with and responded quickly. We were supposed to fly into Miami the morning Hurricane Milton made land fall so our trip was cancelled. Based on the weather circumstances the owner worked with us and refunded our payment. We are in the process of re-planning our trip and will stay here in the future! "
Overlooking the Lagoon and Pool Includes Use of Golf Cart & 2 Kayaks

907 Mariners Club | 3 Bed, 3 Bath

10.0 out of 10, Exceptional, (5)
"This was a great spot to escape the winter weather in the north. The property was excellent and just as described. Would have liked a direct check-in rather than having to stop at the office, but it was in the way. Also some basic starter supplies would have been nice like some coffee pods, sweetener and some basic spices. The amenities such as the gym and pool were great. Definitely would stay here again. Highly recommend. "
907 Mariners Club | 3 Bed, 3 Bath

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (73)
"We had a great time. The accommodations had everything we needed. We loved having access to kayaks and paddle boards. Great and safe area to walk and ride bikes. They had fire pits and a great rock peninsula area to view sunsets and sunrises. There was a marina with fishing opportunities leaving area marina. The only negatives were no working bikes and not a fourth bedroom. It really was 3 bedrooms with a den area with a couch that made a bed.Would go again! Norman, the property manager, was the...
VOTED BEST KEY LARGO VACATION RENTAL

NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH

9.8 out of 10, Exceptional, (185)
"Our stay was perfect. The house had everything we needed. It was clean, well stocked with basic supplies, and more such as toys, chairs for the beach to name a few.The house was very comfortable. Martha was quick to respond and very easy to communicate with. We traveled with 2 young children who enjoyed the playground and the pool daily. It was a perfect week."
The price is €1,094
includes taxes & fees
12 Mar - 13 Mar
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH

NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH

9.8 out of 10, Exceptional, (158)
"Property was conveniently located to lots of activities. Easy access to main road. The pool water temperature was perfect for January. I’m so glad there was a golf cart for use. This was very helpful getting around the property and to the beach area. The beach area was adorable. Loved the tiki hut tables, picnic area and walkout. "
The price is €1,094
includes taxes & fees
13 Mar - 14 Mar
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (5)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

10.0 out of 10, Exceptional, (99)
"We loved the location and the property. The condo unit had all kinds of amenities and the condo area had a lot also. 3 pools, a lagoon, and the ocean a five minute walk away or you can drive a golf cart around. Can’t wait until we can do a return trip!"
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

9.8 out of 10, Exceptional, (141)
"We had a wonderful week at this property. The location of the unit was perfect, right at the start of the lagoon and close to one of the pools. Our favorite was the jetty at sunset and the beach during the day. The host was exceptionally responsive when I contacted her with any questions and we used the owners recommendations for fishing and restaurants, both of which were great! A wonderful family vacation! "
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

10.0 out of 10, Exceptional, (109)
"This property is perfect for a family vacation. The unit is spacious with a great view of the pool and water. Walkable to restaurants and boat rental. If you ever thought about skydiving, definitely go to I skydive Miami. Very professional with amazing views. "
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
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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Other property types in Islamorada

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1407)
"Everything was great-we did have an issue with our a/c but we were only there two nights so we didn't worry with having them look at it. Just reported as we left the property. Loved the place overall!"
The price is €386
includes taxes & fees
24 Feb - 25 Feb
Chesapeake Beach Resort

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1212)
"Our stay was simply outstanding !!"
The price is €426
includes taxes & fees
25 Feb - 26 Feb
Amara Cay Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1035)
"The property had a great resort feel to it. Very clean, and the staff was great. Also, the no smoking rule was great - especially around the pool and beach area."
The price is €494
includes taxes & fees
2 Mar - 3 Mar
Cheeca Lodge & Spa
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.