Holiday Homes in Islamorada

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Islamorada and around

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Outdoor pool, a heated pool

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (57)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Charming Home in Key Largo
Fridge, microwave, oven, stovetop

Charming Home in Key Largo

9.8 out of 10, Exceptional, (23)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is €364
includes taxes & fees
13 Aug - 14 Aug
Charming Home in Key Largo
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Outdoor pool, a heated pool

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

2.5 star property
10.0 out of 10, Exceptional, (18)
"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
208 Mariners Club Key Largo | 3 Bed, 3 Bath
A heated pool

208 Mariners Club Key Largo | 3 Bed, 3 Bath

9.8 out of 10, Exceptional, (87)
"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "
208 Mariners Club Key Largo | 3 Bed, 3 Bath
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
Outdoor pool, a heated pool

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

10.0 out of 10, Exceptional, (1)
"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

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

9.8 out of 10, Exceptional, (65)
"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (18)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Still time for that last minute summer glow! Stay w us @ Mariner's Club 606
Pool

Still time for that last minute summer glow! Stay w us @ Mariner's Club 606

10.0 out of 10, Exceptional, (137)
"Nice location with lots of restaurant choices, pools and especially the Grotto were awesome, Tarpon feeding was our favorite nearby activity."
The price is €794
includes taxes & fees
10 Aug - 11 Aug
Still time for that last minute summer glow! Stay w us @ Mariner's Club 606
Perfect Choice! With Stunning Views of the Island, Private Beach, Pet-Friendly
Property grounds

Perfect Choice! With Stunning Views of the Island, Private Beach, Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Clean and friendly. Great dining close by."
The price is €149
includes taxes & fees
7 Sept - 8 Sept
Perfect Choice! With Stunning Views of the Island, Private Beach, Pet-Friendly
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (81)
"We had a great stay! We loved having kayaks, snorkels, a lagoon and the ocean and everything nearby. We loved feeding the fish on the property. The kitchen is well stocked with everything we needed for making meals. Nice restaurants nearby! Thanks for meeting us, Norman - that was very helpful!!"
VOTED BEST KEY LARGO VACATION RENTAL
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (55)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Property grounds

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

9.8 out of 10, Exceptional, (163)
"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Outdoor pool, a heated pool

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

10.0 out of 10, Exceptional, (8)
"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
611 Mariners Club Key Largo | 4 Bed, 4 Bath
A heated pool

611 Mariners Club Key Largo | 4 Bed, 4 Bath

9.0 out of 10, Wonderful, (96)
"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "
611 Mariners Club Key Largo | 4 Bed, 4 Bath
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
A heated pool

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

9.8 out of 10, Exceptional, (153)
"Great place! Exactly as described."
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Outdoor pool, a heated pool

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

9.6 out of 10, Exceptional, (8)
"Me my wife and 2 kids 18 & 19 had a great time. Loved the lagoon and the local places to eat and drink. "
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Snappers - King Room w/ Ocean View Wifi
Terrace/patio

Snappers - King Room w/ Ocean View Wifi

The price is €91
includes taxes & fees
10 Aug - 11 Aug
Snappers - King Room w/ Ocean View Wifi
Beautiful two- story beach house
Terrace/patio

Beautiful two- story beach house

Beautiful two- story beach house
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (184)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The hotel is very well located. It was a very comfortable place and Jeff was very nice and made great omelettes in the morning"
Juan Andres 2-night trip
Posted 18 hours ago
Chesapeake Beach Resort