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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Islamorada Holiday Homes

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

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
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Relax by the ocean with a clear view, lounge chairs, and a curved pool surrounded by lush greenery.

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

10.0 out of 10, Exceptional, (183)
"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
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Relax by the pool surrounded by palm trees and lounge chairs.

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
Florida Keys Townhouse For Rent 2/2
Relax under the shade of thatched-roof structures, surrounded by sandy ground and natural rocks.

Florida Keys Townhouse For Rent 2/2

9.4 out of 10, Exceptional, (170)
"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"
Florida Keys Townhouse For Rent 2/2
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Enjoy ocean views from the resort's two-story buildings with balconies.

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (193)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Charming Home in Key Largo
Kitchen features a central island with a countertop, surrounded by cabinetry and a refrigerator, microwave, and oven.

Charming Home in Key Largo

9.8 out of 10, Exceptional, (22)
"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 £317
includes taxes & fees
13 Aug - 14 Aug
Charming Home in Key Largo
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Terrace/patio

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Relax by the pool under the stars, surrounded by lush trees and a thatched-roof structure.

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
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Relax on the beach with lounge chairs and enjoy the tranquil atmosphere.

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

9.8 out of 10, Exceptional, (102)
"beautiful and quite neighborhood. "
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Relax in a shaded beachside haven with a thatched-roof structure, comfortable seating, and stunning ocean views.

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
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas nearby.

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
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Relax by the central pool surrounded by lush greenery and palm trees, with sun loungers and umbrellas at your disposal.

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!
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Relax by the resort's pool surrounded by lush greenery and comfortable lounge chairs.

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (93)
"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Enjoy a beach view from the large windows in this room, featuring a seating area with a sofa and armchairs.

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
611 Mariners Club Key Largo | 4 Bed, 4 Bath
Relax by the pool surrounded by palm trees and enjoy the serene atmosphere.

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
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Relax by the pool surrounded by lush tropical vegetation and a marina view.

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

10.0 out of 10, Exceptional, (38)
"Was a nice property and pleasant enough for our stay."
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Keys Relaxing Getaway
Property grounds

Keys Relaxing Getaway

10.0 out of 10, Exceptional, (56)
"Beautiful,clean, great location"
Keys Relaxing Getaway
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Surrounded by lush greenery and a serene water body, this resort offers a tranquil retreat amidst a tropical setting.

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
Key Largo Sunset Estate
Enjoy a serene beachfront setting with a clear ocean view, a wooden pier, and lush greenery surrounding the sandy beach.

Key Largo Sunset Estate

10.0 out of 10, Exceptional, (56)
"We loved our stay! Plenty of room for all of us, amazing view, beautiful sunsets, and live music every night."
Key Largo Sunset Estate
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Relax by the serene pool surrounded by lush greenery and palm trees.

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

9.6 out of 10, Exceptional, (29)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
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
"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other things to do outside of the resort, bikes are available to get around locally. Rooms were clean and comfortable. The rooms on the ocean were recently remodeled. The property is beautiful and easy to navigate. Oceanside live music at night was really nice, lots of families congregated on the beach to enjoy the ocean breeze and entertainment."
Lacey 3-night trip
Posted 1 day ago
Cheeca Lodge & Spa