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Compare 684 Vacation Homes in Islamorada with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (178)
"We had 5 adults stay over the Christmas holiday and had a wonderful time! I’m a “clean fanatic” and found the home very clean. It was awesome to have extra amenities such as toilet paper, detergent, soap, and even air freshener available! That was such a great touch and worth 5 plus stars! The only negative comment I have is that house of this quality should have much better mattresses and pillows. The pillows were terrible but an easy fix. "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

10.0 out of 10, Exceptional, (43)
"Great location second bedroom a little cramped with two beds. Pools are good. Quiet setting and lagoon is nice, "
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, (88)
"We had the best week at Shanie's lovely house! Location is even prettier in person!! The pool was always warm and clean, thanks to JP. We would definitely visit again."
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

8.8 out of 10, Excellent, (9)
"The house was perfect for our large family, different spaces for everyone to spread out. Very happy with our stay in islamorada"
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

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

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

2.5 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay. Great location and super clean."
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

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..

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

9.8 out of 10, Exceptional, (9)
"Overall great spot just south of Robbie’s and all the main areas of Islamorada. Nice accommodations that have been recently upgraded. Pool was only a short walk away. I missed on the property listing that it only had one bathroom. For our family with two teenagers we needed two bathrooms. That’s the only complaint though. Everything else was great."
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, (125)
"We loved our experience. The location was perfect, close to everything and in impeccable condition."
The price is AED 1,315
AED 2,544 total
includes taxes & fees
26 Jan - 27 Jan
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

10.0 out of 10, Exceptional, (14)
"Please note - the address is Overseas Highway, but to access the property, you have to go to Cortez Dr. Booked for 3 days to visit with family living in Islamorada. We were so pleased with the accommodations. Very clean, small, but plenty of space. Fire pit, swimming pool, washer/dryer, kitchen had everything needed to prepare meals (great for breakfast with grandkids), comfortable beds, nice shower, cold A/C (so cold you might need a throw blanket). One of the nicer rentals we have stayed...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Kawama G12 Upscale OceansideVilla with Marina 2/2

10.0 out of 10, Exceptional, (5)
"Good property for family vacations. Clean, open space and nice kitchen. "
Kawama G12 Upscale OceansideVilla with Marina 2/2

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

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

10.0 out of 10, Exceptional, (20)
"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, (4)
907 Mariners Club | 3 Bed, 3 Bath

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

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (71)
"Great location. wonderful amenities and Norman was very helpful in explaining and touring the entire property Lots of attractions on the Key and many very good restaurants.."
VOTED BEST KEY LARGO VACATION RENTAL

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

9.8 out of 10, Exceptional, (155)
"We had an incredible stay at your Key Largo property! It was the perfect location for our family Christmas vacation, offering a peaceful, relaxing atmosphere and easy access to nearby attractions.The property itself was beautifully maintained and clean. The jetty was a highlight, providing hours of fun and relaxation on the water. We also loved the spacious outdoor areas, tennis court, swimming pool (my youngest's favorite), and fun commute with a golf cart. Additionally, the property has a...
The price is AED 1,627
AED 3,194 total
includes taxes & fees
24 Jan - 25 Jan
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH

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

9.8 out of 10, Exceptional, (183)
"Check in/ out was easy. Host is very responsive. Very clean and well stocked. There was a wedding the weekend we were there so they took over the tiki hut area and played loud music the Friday and Sunday nights, so that was unfortunate. Lagoon was awesome, we bbq’d by the ocean every night (which we loved) so be sure to get charcoal as there is no gas bbq onsite. Aside from the loud wedding no complaints! I wouldn’t hesitate to book it again. "
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH

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

10.0 out of 10, Exceptional, (98)
"Well kept property. Great location. The owner is very responsive and did a great job preparing the property for our stay "
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, (136)
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VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
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

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (398)
"This is a great little place to stay at a very good rate. It is walking distance to some amazing restaurants. The room had been updated, it was clean. Staff was friendly but I wouldn’t say they go out of their way. The beach is good for relaxing at but it’s pretty shallow a long way out so not much for swimming. The pool was nice but you lose the sun early due to placement. I’d stay here again."
The price is AED 585
AED 848 total
includes taxes & fees
23 Jan - 24 Jan
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (45)
"This property was immaculate, a great blend of an upscale hotel feel with a vacation rental. We loved all the amenities. Would highly recommend!"
The price is AED 1,683
AED 2,096 total
includes taxes & fees
12 Feb - 13 Feb
The Islands of Islamorada

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

9.8 out of 10, Exceptional, (6)
"We had a wonderful visit. We come every Thanksgiving. Anglers is wonderful place to stay."
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
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.