Holiday Homes in Islamorada

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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Holiday Homes in Islamorada and around

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
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)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
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, (169)
"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, (191)
"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, (21)
"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 €393
includes taxes & fees
24 Jul - 25 Jul
Charming Home in Key Largo
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
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
Fridge, microwave, oven, stovetop

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

7.4 out of 10, Good, (3)
"Three generations stayed very comfortably in this great house. It was located great for food and activities!"
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
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, (15)
"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
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, (92)
"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
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, (7)
"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
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, (95)
"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
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
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, (101)
"Beautiful condo in great location. Great beds!! "
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Keys Relaxing Getaway
Property grounds

Keys Relaxing Getaway

10.0 out of 10, Exceptional, (56)
"Beautiful,clean, great location"
The price is €625
includes taxes & fees
22 Jul - 23 Jul
Keys Relaxing Getaway
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

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
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)
"Enjoyed our stay. Lots to do if you’re wanting a relaxing day or a day of swimming, tennis, walking or cycling. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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
NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
Relax in a shaded beachside haven with comfortable seating and a table.

NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH

9.8 out of 10, Exceptional, (189)
"We had a wonderful time at Casa Azul. The house was super clean and great location in the complex near the pool, beach and pickleball courts. We would definitely stay here again!"
NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Enjoy a serene beachfront setting with access to the ocean and a patio surrounded by lush greenery and palm trees.

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

9.4 out of 10, Exceptional, (96)
"Oceans views for miles! Great pool. "
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Absolutely heavenly! Comfy beds, clean and an fun perks like a local shuttle and water taxi! Cute activities and amazing sister resort privileges! Thank you so much! "
Sanda 2-night trip
Posted 1 day ago
La Siesta Resort & Villas