Vacation Rentals & House Rentals in Florida Keys

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59 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 13 minutes

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Price per night from

$236

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful location” My husband, son, and I had a fantastic vacation here. The private boat dock and Bay Area was perfect for our needs. We were out in the gulf in a few minutes and could reach the Atlantic via Vaca Pass or 7 Mile bridge in just a short boat ride. The house itself was the perfect size for the 3 of us(& 2 shelties), giving each of us our own space. The view from the house is great. We watched tarpon, turtles, and dolphin!! The airport right behind us was not an issue!! In fact, we thought it was kind of cool to watch some of planes/helicopters!! The storage area with the bait fridge/freezer was a great plus!! There were 2 things that I noticed could improve (but by no means a reason to not stay here!!). First there was not any pantry storage. We just used the island top. No big deal. And the lint screen for the dryer was falling apart. Again no big deal. I would not hesitate to stay here again!!

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Price per night from

$200

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 11 minutes

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Price per night from

$228

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 23 minutes

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Price per night from

$189

2 Great Waterfront FL Keys Homes - 1 Low Price

Marathon house

4 bedrooms / 4 bathrooms / sleeps 12

“Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I loved how the kitchen was fully stocked with any possible cooking thing we needed. Everything worked perfect and was up to date.

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$372

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$259

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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$138

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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Price per night from

$427

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 12 minutes

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Price per night from

$258

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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$212

Islamorada 2-bedroom Condo

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic Views” This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex has a private heated poool, work out room and sauna. The grounds are cleaned every morning and the manager responds to needs promptly. We will again stay here in 2013. repeat customers. That will be our 6th year in a row at Sea Gulls.

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$185

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 30 minutes

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Price per night from

$1,259

Keys Townhouse

Tavernier townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$229

Tropical Keys Home - Gulf View, 40' Dock, Kayak

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Great Location” The house is wonderful, clean and airy with everything for a comfortable vacation. The area was nice and quiet and everyone we met was friendly. Joe was great to deal with, he was helpful and answered any queries we had promptly . We have already booked for next year.

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$151

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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Price per night from

$492

Beautiful Bayside View with Swimming Pool

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 40 minutes

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Price per night from

$822

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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$950

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. 1 hour 58 minutes

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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. 3 hours 33 minutes

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Price per night from

$166

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 47 minutes

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Price per night from

$258

Florida Keys, Marathon_March 30-April 6, 2019 (1 full week)

Lower Keys villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Boat available

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Price per night from

$426

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

$345

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

Key West condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

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Price per night from

$919

The Enchanting Seahorse

Key Largo house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$373

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

$1,465

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

$494

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 minutes

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Price per night from

$476

Atlantis House Garden Suite

Key West cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$205

Waterfront Condo with Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$373

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

$529

Waterfront Penthouse in Old Town Seaport (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$640

Term Charterboat w/ FREE Sunset Cruise

Key West houseboat

2 bedrooms / 1 bathroom / sleeps 3

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Price per night from

$343

Florida Keys Oceanfront Paradise

Long Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$192

The Blue Pelican - Comes With 6 Passenger Gas Golf Cart

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$575

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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Price per night from

$344

Oceanfront Luxury in Old Town Seaport (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$640

4/3 Gorgeous, Private Home w/open Bay & SwimSpa

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 12

“Wonderful” This rental was easy and the accommodations exceeded my expectations. Upon arrival I was greeted by amazing views from everywhere on the property. The house was clean and comfortable and we had everything we needed to make our stay perfect.

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Price per night from

$247

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