Search Vacation Homes in Islamorada

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 687 Vacation Homes in Islamorada with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (183)
"We enjoyed our stay can't think of any issues Defiantly would go back "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Property grounds

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

9.8 out of 10, Exceptional, (46)
"We stayed a week in the wonderful resort at Kawama. The lagoon was right in front of our unit. There were beautiful tropical fish in the lagoon as well as tarpons and lobster! The 2 pools were heated and delightful to swim in. We love walking out to the end of the jetty each evening to watch the sunset. It was a fantastic place to spend a week and soak up the sun."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Heated pool

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

9.4 out of 10, Exceptional, (89)
"We were fortunate to get just one day of rain, and otherwise had wonderful weather, which was great because the outdoor space at this property is wonderful. There is a large area to play soccer or throw a ball, as well as beach, long and low dock, and kayaks to use. The outside space is truly what makes this house special. The location is very good and easy to get to -- you're just a handful of miles from some of the more touristy things in Islamorada, making this a quiet spot that still has...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Oasis Pool Overhead

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

2.5 star property
10.0 out of 10, Exceptional, (4)
"It is a lovely property! Ee had a peaceful, relaxing stay!"
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
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
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
Property grounds

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

8.8 out of 10, Excellent, (10)
"Great location with access to Gulf and Atlantic (a short ride away). Super clean and exactly as advertised. No disappointments. Hosts very responsive to inquiries."
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
Islamorada Boaters Paradise with 70' Dock and private beach access..
Pool

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..
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
Property grounds

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
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More
Living area

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

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

9.6 out of 10, Exceptional, (10)
"We stayed at this home during the time between Christmas and New Years (me, my husband and our two teenage children). The house is nice but, be aware it is small. We had a day with rain and with everyone being in the house it just felt cramped. When we arrived the toilet was running constantly. We had to take the top off of the toilet and fix it every time we used the restroom until a repairman came the following afternoon to fix it. If you are traveling to the area during this time of...
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Living room

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

9.6 out of 10, Exceptional, (127)
"Clean, great location, plenty of room,"
The price is AED 1,800
AED 3,200 total
includes taxes & fees
24 Feb - 25 Feb
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Overlooking the Lagoon and Pool Includes Use of Golf Cart & 2 Kayaks
Living area

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

10.0 out of 10, Exceptional, (21)
"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
Ground floor wet bar and foosball table

907 Mariners Club | 3 Bed, 3 Bath

10.0 out of 10, Exceptional, (5)
"This was a great spot to escape the winter weather in the north. The property was excellent and just as described. Would have liked a direct check-in rather than having to stop at the office, but it was in the way. Also some basic starter supplies would have been nice like some coffee pods, sweetener and some basic spices. The amenities such as the gym and pool were great. Definitely would stay here again. Highly recommend. "
907 Mariners Club | 3 Bed, 3 Bath
VOTED BEST KEY LARGO VACATION RENTAL
By The Sea...

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (73)
"We had a great time. The accommodations had everything we needed. We loved having access to kayaks and paddle boards. Great and safe area to walk and ride bikes. They had fire pits and a great rock peninsula area to view sunsets and sunrises. There was a marina with fishing opportunities leaving area marina. The only negatives were no working bikes and not a fourth bedroom. It really was 3 bedrooms with a den area with a couch that made a bed.Would go again! Norman, the property manager, was the...
VOTED BEST KEY LARGO VACATION RENTAL
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
Dining

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

9.8 out of 10, Exceptional, (185)
"Our stay was perfect. The house had everything we needed. It was clean, well stocked with basic supplies, and more such as toys, chairs for the beach to name a few.The house was very comfortable. Martha was quick to respond and very easy to communicate with. We traveled with 2 young children who enjoyed the playground and the pool daily. It was a perfect week."
The price is AED 2,362
AED 4,105 total
includes taxes & fees
12 Mar - 13 Mar
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
Living area

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

9.8 out of 10, Exceptional, (158)
"Property was conveniently located to lots of activities. Easy access to main road. The pool water temperature was perfect for January. I’m so glad there was a golf cart for use. This was very helpful getting around the property and to the beach area. The beach area was adorable. Loved the tiki hut tables, picnic area and walkout. "
The price is AED 2,362
AED 4,105 total
includes taxes & fees
13 Mar - 14 Mar
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Grotto

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

2.5 star property
10.0 out of 10, Exceptional, (5)
"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
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
Second Floor Living Room

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

10.0 out of 10, Exceptional, (99)
"We loved the location and the property. The condo unit had all kinds of amenities and the condo area had a lot also. 3 pools, a lagoon, and the ocean a five minute walk away or you can drive a golf cart around. Can’t wait until we can do a return trip!"
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
PROFESSIONALLY DECORATED DINING AREA

VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

9.8 out of 10, Exceptional, (141)
"Convenient location, clean and well equipped kitchen. "
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Relaxing porches overlooking pool and ocean

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

10.0 out of 10, Exceptional, (109)
"This property is perfect for a family vacation. The unit is spacious with a great view of the pool and water. Walkable to restaurants and boat rental. If you ever thought about skydiving, definitely go to I skydive Miami. Very professional with amazing views. "
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
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.
Don't see what you're looking for?
See all available properties in Islamorada
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (413)
"Wonderful experience - highly recommend!! From check in to check out was great. All staff were very helpful, property was well kept, relaxing, quiet & very easy location to site’s & restaurants. "
The price is AED 842
AED 1,006 total
includes taxes & fees
26 Feb - 27 Feb
Breezy Palms Resort
The Islands of Islamorada
Bar (on property)

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is AED 2,971
AED 3,545 total
includes taxes & fees
24 Feb - 25 Feb
The Islands of Islamorada
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
Exterior

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (76)
"Great and clean place to stay. Chris was the perfect host. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
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.