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Vacation Rentals & House Rentals in Florida Keys

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66 house rentals

Amazing Ocean View Condo on the Beach!

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$279

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$184

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 28 minutes

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$212

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$228

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

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$264

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

Responds fast! avg. 1 hour 44 minutes

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Price per night from

$280

Laid Back and Waterfront (Monthly Rental)

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 8

“Wonderful way to start a new year” We truly enjoyed our stay in Key Largo. The house had everything we needed. We enjoyed fishing in the canal and there were even manatees two different days in the canal. The location of this property is excellent and allows for many great choices of restaurants. Alex was very responsive and helped us answer a lot of questions before and during our visit. We would love to return again.

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$155

LISENCED MGR! BRAND NEW & TOTALLY RENOVATED 2/2 SUITE! OCEANFRONT BEACH RESORT!

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“A great location for accomplishing our interests while visiting” This rental was a perfect set up for two people - also very clean, convenient and seeing the egret's nest outside the patio was special. The beach chairs in the closet need attention as it was nice to have Harry Harris park near by. Thank you.

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$206

Gulf View Three - 3 bedroom, 3 bathroom, Gulf Side

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Paradise Getaway...” My Husband and I were more than thrilled to take our vacation at the Fisherman's Haven with Dock. Right on the inlet he was able to fish and enjoy the beautiful scenery Fishing license was easy to obtain from the local Kmart just south. We were able to grill out and enjoy eating outside or dine in the beautiful and very accommodating Kitchen which was fully stocked with more than one could need. Everything was very clean.! Having a washing machine was perfect. Beds very comfortable also. We were able to drive to various Keys and enjoyed Key West so much we went twice. Thank You Rent my Island for an a+ and 5 star *** Experience!!! Ps Sharky"s just south on a! has .25 wings and shrimp from 4-6! We will definitely come back!

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$425

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$1,286

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.

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$229

Keys Townhouse

Tavernier townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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$257

Gulf View Place w/ Dock, Pool, Kayaks, Sandy Shore

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Awsomely relaxing yet centrally located for easy day trips.” Very clean and nicely equipped with everything needed for a relaxing and comfortable at home feel vacation. Lots of room for family reunions. Centrally located in the Keys so day trips either north or south are easy. Don't miss Savannah Sweets Bakery and Cafe for the best key lime pie. Property manager a phone call away but never needed as everything was in good working order. Owners very nice and have thought of everything. Pool more of an oversized hot tub but does the trick on hot days. Can't wait to return!!

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$490

Dolphin Oasis 4bdr/4bth Pool/hot tub 115' dockage

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Fantastic house, in excellent location and managed directly by the super-efficient and friendly owner!” This house is ideally situated in Marathon - halfway between Key Largo and Key West. Easily accessible with great local amenities. There is ample comfortable accommodation inside and fantastic outdoor facilities including a large pool and hot tub and various seating areas and fire pit. We could even watch a manatee swimming at the dockside of the house! Craig (the owner) made contact with us soon after we arrived and made every effort to ensure that our holiday was the way we wanted it to be - he could not have been more friendly or accommodating.

Responds fast! avg. 2 hours 1 minutes

Travelers’ Choice award

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Price per night from

$425

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful” This house was beautiful, well equipped, clean, and had everything we needed for our perfect stay. It looked exactly like the pictures shown, and I loved the upper deck and hammock for relaxing. Marathon is especially perfect for a vacation in the Keys as it is located in the middle of them, and only a short, pleasant ride to any of the others. Great restaurants in Marathon, and we enjoyed all of them. Booking with "Coconut Chuck" was so easy, and we even received a gift bag of goodies in the mail before our rental. So thoughtful. Highly recommend.

Responds fast! avg. 1 hour 37 minutes

Travelers’ Choice award

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Price per night from

$117

Luxury 3BD/3B Penthouse Condo at Galleon Resort, Old Key West

Key West condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$1,014

Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 20

Marathon house

8 bedrooms / 6 bathrooms / sleeps 20

“Awesome location, close to many popular destinations.” My husband and I really enjoyed our vacation to Marathon Fl. Our vacation home was very clean and close to many great restaurants and beaches. We used the kayaks, swam in our own pool and sat out on the deck to just watch the world go by. We would highly recommend Rent My Island.

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$1,016

Atlantis House Master Suite

Key West cottage

1 bedroom / 1 bathroom / sleeps 2

“Beautiful place located just across the street from the beach. The owners Capt. Steve and Kayla were wonderful hostess.” We arrived the week of Fantasy Fest, not knowing exactly what we were getting into, but had a great time. Lots of things to do or just lay around and relax. Our Master suite was perfect and the owners Steve and Kayla made us feel very welcome. Capt. Steve even went out of his way to take us fishing and then he prepared what we caught the next day for lunch. YUMMY! Perfect place to stay! Thank You, Steve and Kayla.

Responds fast! avg. 1 hour 33 minutes

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Price per night from

$289

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 11

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Price per night from

$386

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$553

Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate

Key Largo house

6 bedrooms / 5 bathrooms / sleeps 16

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

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Price per night from

$1,640

Atlantis House Garden Suite

Key West cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 33 minutes

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Price per night from

$259

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$327

KEY WEST LA BRISA CONDO - North Building

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$229

Term Charterboat w/ FREE Sunset Cruise

Key West houseboat

2 bedrooms / 1 bathroom / sleeps 3

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Price per night from

$385

SEAPORT SUMMIT at Galleon Resort, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$567

Marlin Bay Resort & Marina - Modern Home within Newly Launched Luxury Resort

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$482

Waterfront Condo with Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$384

Exquisite Newly Remodeled 4 BR Key Colony Beach Home with Private Dock and Pool

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 59 minutes

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Price per night from

$652

Florida Keys Oceanfront Paradise

Long Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$202

BAYSIDE CONDO WITH BOAT

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

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$344

* Key West Beach Condo Casa Coastal East Open Nov-Feb2021 *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$134

Sandy Shore Place 100' Dock, Pool, Kayaks,Sleep 10

Marathon house

4 bedrooms / 2 bathrooms / sleeps 10

“Everything we hoped for!” Service was great, from booking, until the finish of our stay. Place was clean, a little worn, but clean. Our favorite things included the location, right on the beach, and easy access to anything, like stores, restaurants, churches, airport, etc... It is private. The least thing we liked is after a storm the grass all came in and covered the water, but not much can be done about that. We are definitely intending to book again next year. Thank you for a great vacation!

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Price per night from

$457

Family Friendly With Swim Spa

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 12 minutes

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Price per night from

$337

Bayfront Vacation Home Villa Rental Bayside Beach View

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

“Lobster season trip” Beautiful villa had everything we needed and the location was perfect. We came to experience the lobster season. Brought our own boat once we found a public ramp at the Caribbean Club we were able dock our boat behind the villa and that made our boat trips so much easier. Absolutely loved Key Largo.

Travelers’ Choice award

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Price per night from

$201

Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat

Conch Key cottage

2 bedrooms / 1 bathroom / sleeps 6

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Responds fast! avg. 3 hours 44 minutes

Travelers’ Choice award

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$289

Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*

Key Largo cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Key Largo” Our stay was great. The house was awesome and we would go swimming and fishing right off the dock. Its a great place for the family to have a vacation.

Travelers’ Choice award

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Price per night from

$231

Key Largo Rental Fantastic Views

Key Largo condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$344

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