Search Vacation Homes in Islamorada

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

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

Beach
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
10.0 out of 10, Exceptional, (160)
"The property was perfect for our celebration. Great location with many restaurants and activities very close by. There was a great gazebo with a charcoal grill that worked perfect for our family. The owner was super responsive. We would definitely stay again!!"
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Outdoor pool, a heated pool
Amazing Florida Keys Retreat!
10.0 out of 10, Exceptional, (52)
"Lovely property in a great location! Our family enjoyed our stay in this lovely place."
Amazing Florida Keys Retreat!
On the beach
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
10.0 out of 10, Exceptional, (96)
"My family and I had a wonderful week at Angler's Reef. The house was absolutely beautiful, clean and very well kept. The kitchen was fully stocked which was great as we cooked several meals while visiting. The pool and grounds are well maintained, and the community has a safe, friendly vibe. We would highly recommend this home and Angler's Reef."
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Save an average of 15% on thousands of hotels when you're signed in
Property grounds
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (59)
"My family and I had a fantastic visit. The Home was very clean and the property was beautiful."
VOTED BEST KEY LARGO VACATION RENTAL
Exterior
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (8)
"Beautiful, spotlessly clean, comfortable, well appointed, great pool! A lovely little cottage that had everything we needed! Perfect stay!"
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (1)
"Very hood stay"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
Outdoor pool, a heated pool
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
10.0 out of 10, Exceptional, (18)
"Exceeded all expectations"
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
Outdoor pool, a heated pool
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
10.0 out of 10, Exceptional, (86)
"Nice property and convenient location. Communication was very good!"
The price is $343
$623 total
includes taxes & fees
May 29 - May 30
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
Lake
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
10.0 out of 10, Exceptional, (58)
"Very nice, spacious, well-provisioned house with some water view from the back deck. Great central pool, and a good dock you can rent for a reasonable rate if you're renting a boat. Cute neighborhood, central to tons of restaurants and amazing activities. Rob & Jen were very communicative hosts who responded to every request within an hour."
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Beach | Beach nearby
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (23)
"We loved the beautiful and quiet location of our unit within the facility and also enjoyed all of the amenities. Having the living quarters downstairs and bedrooms on the second story made it easy to accommodate early and late risers. If you like to do your own cooking, you may want to think about bringing measuring cups and perhaps ziplock baggies or wrap for any leftovers. The cupboards were stocked with some nice spices and other surprises. We had a lovely time and would definitely consider...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Property grounds
Kawama Townhome with Amazing Master View - Direct Waterfront on a Tidal Lagoon!
9.8 out of 10, Exceptional, (138)
"Great place to stay. Beautiful grounds. We enjoyed the lagoon and the tennis courts. The condo is nicely decorated. Great layout and views from the balcony."
Kawama Townhome with Amazing Master View - Direct Waterfront on a Tidal Lagoon!
A heated pool
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
9.8 out of 10, Exceptional, (141)
"We are so grateful we got to experience this beautiful property. The whole community is well maintained and immaculate. It’s a very quiet and peaceful neighborhood but still close to stores, restaurants and outdoor activities. The condo is also well maintained and spotless. The decor is warm and welcoming. I especially appreciated the high quality towels and linens. The kitchen is well equipped, we especially enjoyed having the grill ( again very clean). My only suggestion would be is to have...
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
Living area | Smart TV, DVD player, books, music library
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
9.8 out of 10, Exceptional, (149)
"Great Place to stay. Spacious and very clean."
The price is $443
$878 total
includes taxes & fees
Jun 9 - Jun 10
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
Property grounds
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
9.8 out of 10, Exceptional, (146)
"Nice property, in the corner of the complex, patio was perfect for drying wet dive gear. Bikes and golf cart available but walking through the lagoon and pools is very nice. Sunsets out on the jetty were beautiful."
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Property grounds
Overlooking Salt-water Lagoon- Free Golf Cart + 2 Kayaks
9.8 out of 10, Exceptional, (20)
"Andy was terrific"
Overlooking Salt-water Lagoon- Free Golf Cart + 2 Kayaks
Outdoor dining
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS
9.8 out of 10, Exceptional, (175)
"Condo had everything and more which was great! Very close to restaurants and activities. Golf cart was a big bonus. We really enjoyed our stay!"
The price is $483
$928 total
includes taxes & fees
Jun 7 - Jun 8
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS
Property grounds
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
9.8 out of 10, Exceptional, (129)
"Condo was as advertised. The complex is perfect for families with children. Will definitely come back."
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
On the beach, beach towels
KEYS LIFE FOR ALL AGES, 🍹☀️🏊‍♂️⛱🎣
9.8 out of 10, Exceptional, (173)
"All good"
KEYS LIFE FOR ALL AGES, 🍹☀️🏊‍♂️⛱🎣
Beach
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
9.8 out of 10, Exceptional, (53)
"Plenty of room for my family. Loved the setting, hanging out on the multiple porches, walking on the jetty, and my son loved the lagoon. Just a few minutes to the state park as well as other attractions. Owner was responsive with a couple of questions. Highly recommend"
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
Property grounds
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
9.6 out of 10, Exceptional, (84)
"The house was cute and clean and very comfortable. We had no issues. Had a great time"
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
Don't see what you're looking for?
See all available properties 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.

Other property types in Islamorada

Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (1)
"Very hood stay"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
Property grounds
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
9.6 out of 10, Exceptional, (71)
"The Irvine’s are great hosts, and we had a wonderful week. This house is a great location for boaters, with easy access to both the gulf and Atlantic. We will look forward to another stay."
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, (35)
"My wife and I have been traveling to Islandmorada for many years and this place is what we have been searching for. Clean, quaint, all the amenities of a large restort withiut the corporation feel. Absolutely refreshing!"
The Islands of 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.

Islamorada Vacation Homes information

Number of reviews
Accommodation
Vacation Homes
Lowest Price
Highest Price

Recent reviews of Islamorada hotels
Expedia verified reviews