Beachfront vacation rentals in Islamorada

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Popular amenities for Islamorada beachfront rentals

Beachfront home rentals with a pool

Superhost
Home in Key Colony Beach
5 out of 5 average rating, 4 reviews

Huge Swim Spa~ Incredible Special Fall Pricing

JillRating, 5 stars1 month ago
The house was exactly as described. We used all the things provided. The swim spa was great. Everything was provided to fish. The bikes were so fun to use to get around the area. The paddle board and kayaks were fun for the kids. Sherry was very good at communicating with us. We would definitely go back here!
Superhost
Home in Marathon
4.93 out of 5 average rating, 14 reviews

Sombrero Beach Getaway

MatthewRating, 5 stars1 month ago
We had a great time. We enjoyed the pool, great location, and very clean. The communication with the property manager was also great. We would very much recommend staying here.
Superhost
Home in Marathon
4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

CarolRating, 5 stars9 months ago
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.
Superhost
Home in Marathon
4.95 out of 5 average rating, 20 reviews

4BR Sombrero Beach House on Canal w Dock & Pool

JosephRating, 5 stars3 weeks ago
Matt was super responsive and helpful with any issues we had. The house was comfortable and the proximity to the beach was amazing (5 minute walk). We stayed for a month with a 1 year old and a big dog and found the house perfect for our needs. Manatees even came up to the house on our last day! Super special. Would recommend.
Superhost
Home in Marathon
4.93 out of 5 average rating, 14 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

JoshuaRating, 5 stars3 months ago
We were looking for a great place close to a small beach, an ocean view, which was clean and could house our family comfortably. This place did that and provided a place away from tourist crowds. Very nice place
Superhost
Home in Marathon
4.75 out of 5 average rating, 20 reviews

Sunset Views, Pool and Dock

AllenRating, 5 stars3 weeks ago
We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.
Guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 7 reviews

Paradise Cove!30ft Dock Pool BBQ

WymanRating, 5 stars2 days ago
My family and I had a great time here! It was the perfect house, super clean and just as described! Yuni was always quick to respond and answer any questions. We had no intentions of renting a boat, but just up the road was an easy rental spot and we were able to tie the boat up right outside the door. Everything we needed was within a few minutes and the location was perfect to take a drive down to Key West! We will absolutely plan to return!
Superhost
Home in Key Colony Beach
4.73 out of 5 average rating, 133 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

CherylRating, 5 stars2 months ago
Mary's place was in a very safe and beautiful location. Everyone was friendly and there were endless dining options. There were even local conveniences that I didn't expect nearby such as Dollar Tree, Winn Dixie, Home Depot, etc. Showers had great water pressure, hot water, and had zero sulphur smell. Decor was lovely and ample storage space for your things. A/C and heat works great and no musty smells anywhere. Beds, outdoor furniture and couches very comfortable. Convenient off-street parking. Was too busy to enjoy the cabana amenities but visited it briefly and it looked wonderful. Thank you Mary hope to return in the future!

Beachfront home rentals with a hot tub

Guest favorite
Condo in Tavernier
4.87 out of 5 average rating, 142 reviews

Reel Large END Unit in Ocean Point Suites

ThomasRating, 5 stars3 days ago
We enjoyed our visit to Tavernier. The condo was perfect for our few days off and we appreciated having both a pool and beach. There were many restaurants nearby and grocery shopping was easy as well. Having an end unit was great as it allowed it a lot more light than most of the units in Ocean Pointe. The unit was everything we expected!
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 43 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaryRating, 5 stars2 weeks ago
If you’re looking for a place in the keys Casa Kokomo will not disappoint. This place has it all, is so well equipped, and the location could not be better. We could walk to Publix and Walgreens. The Cracked Conch Cafe is a great little breakfast spot and a must get is the fried cracked conch. My husband worked for Ritz Carlton much of his career in the hospitality industry and Kokomo gives you the same level of luxury you’d expect from the highest level quality hotel brands; from the linens on the beds to the cozy robes. We like to fish and rented a boat that we parked out back on the private dock. The back yard is so private and is an oasis. If you’re like us and you work hard to enjoy your vacation time, choose Casa Kokomo, you won’t be disappointed.
Guest favorite
Condo in Tavernier
4.89 out of 5 average rating, 114 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

EmilyRating, 5 stars3 weeks ago
A beautiful tropical setting. A wonderful view.
Guest favorite
Apartment in Tavernier
4.95 out of 5 average rating, 183 reviews

Boho FL Keys Condo

AmberRating, 5 stars2 weeks ago
Better in person than the photos! The view was amazing. The entire condo was very clean, fully stocked and had everything needed for the beach or pool. We would definitely stay here again! The host was also very responsive and kind.
Guest favorite
Home in Key Largo
4.94 out of 5 average rating, 77 reviews

Ocean Breeze Home

BarbaraRating, 5 stars2 days ago
Lovely home, very spacious and private. Pamela has it set up so that you have access to everything you need for a comfortable stay. I would highly recommend staying here!
Superhost
Townhouse in Marathon
4.82 out of 5 average rating, 138 reviews

Plunge Pool Villa on Blue Water Lagoon

EllaRating, 5 stars1 month ago
We had such a great stay we added another night! Place is well equipped and super clean and the host is very helpful. It's an ideal location if you're looking to vacation with other families, you can grab the next door units and all hang out! As this listing notes you technically can't use the main resort facilities...but we didn't have any problems! It was a great walkable spot for a group getaway. Would stay here again!
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 119 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

SusanRating, 5 stars3 days ago
Nicole’s condo was beautiful! She has thought of everything, from a well-appointed kitchen to shampoo, conditioner and body wash in each shower. The condo is spotless with up-to-date decor and beautiful bedding. The beds were very comfortable too. We slept like babies! The grounds had a huge pool, hot tub and a small beach. The recent additions of a pool-side bar and beach cafe rounded out the amenities. Thank you, Nicole. We hope to come back soon!
Superhost
Home in Key Largo
4.83 out of 5 average rating, 65 reviews

Bayhouse

CheriseRating, 5 stars3 weeks ago
We stayed 5 days with 8 adults-4 couples and it was magical. We gave the kids and their spouses the bedrooms and my husband and I took the sofa bed, which maybe wouldn’t work for most groups but it was worth the property. The amount of almost private beach we had was equivalent to an entire resort or more, it was amazing. You could find fancier accommodations somewhere but never with this much paradise in your front yard. We had an amazing trip we will never forget!!

Pet-friendly beachfront home rentals

Guest favorite
Home in Marathon
5 out of 5 average rating, 15 reviews

Seaside Sunrise. Newly remodeled waterfront

MRating, 5 stars1 month ago
This home was simplistic, clean and a great peaceful location. The hot tub was a nice addition especially because we had cooler weather while we were here. I could make an espresso or regular drip coffee from the appliance provided. The shower was cutting-edge and beds were comfortable. I would recommend this house for anyone that comes to visit the keys.
Superhost
Home in Key Largo
4.84 out of 5 average rating, 436 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

AtRating, 5 stars2 weeks ago
This house was just as described and in a great location in a quiet neighborhood. It was perfect for our family!
Guest favorite
Guesthouse in Marathon
4.94 out of 5 average rating, 18 reviews

The Pink Dolphin House.

ScottRating, 5 stars1 month ago
We absolutely loved Margaret's place! It was picturesque and so fun! We loved the view, the pool, the local restaurants and her home felt very comfortable for my family of five. Thank you Margaret and Phil!!!
Guest favorite
Apartment in Key Largo
4.92 out of 5 average rating, 257 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

MarthaRating, 5 stars2 weeks ago
The studio was just as described. It was great to wake up in the morning and watch the sunrise from the balcony. We had the pool mostly to ourselves and enjoyed kayaking the bay. There was an issue with the keypad but the host remedied it quickly. He was very responsive.
Superhost
Home in Key Colony Beach
4.87 out of 5 average rating, 30 reviews

Coral House: 2/2 Waterfront in KCB w/ King Beds

LucasRating, 5 stars1 month ago
Kristi was very responsive and helped us out with a request early on in the stay. It was really nice to be able to kayak along the water way and we utilized this daily. Overall the place was exactly as described and we enjoyed our time in Marathon.
Guest favorite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Waterfront w/pool and hot tub

LisaRating, 5 stars3 weeks ago
Second time staying here and we really like it! Had a few things we needed help with and were gotten back to quickly. Beautiful property, clean and location couldn’t be better. Also the neighbors are so friendly! A few things need a little TLC in the future but minor and I’m positive it won’t affect an amazing stay. We will be back!
Superhost
Camper/RV in Key Largo
4.87 out of 5 average rating, 110 reviews

Cozy Waterfront Retreat w/ Private Boat Dock +Tiki

SarahRating, 5 stars3 weeks ago
Great location! Outdoor space was beautiful and quiet. Wonderful spot to read a book and drink your coffee. Neighborhood was friendly. Easy to walk or short drive to everything.
Guest favorite
Home in Marathon
4.79 out of 5 average rating, 14 reviews

Casa Marquez

BariRating, 5 stars1 month ago
I cannot say enough good things about the home and the host. The house is actually more beautiful in person than in the pictures. Everything was exactly as described and our 13 day stay for our destination wedding was amazing! We spent most of our time in the pool and dock area and it was so fun to see the manatees in the canal! The pool was so nice and warm, I definitely recommend paying extra to heat the pool. Our host, Rosaly, was so nice and friendly. She was very quick to respond if we needed anything at all. She also went the extra mile for us and put up a Christmas tree which was such a nice surprise! This was our best Airbnb experience by far, and we can't wait to return to Casa Marquez!

Quick stats about beachfront rentals in Islamorada

  • Total rentals

    280 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    150 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Beachfront rentals