Vacation Rentals & House Rentals in Florida Keys

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99 house rentals

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Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 53 minutes

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Price per night from

$287

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

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Price per night from

$287

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$230

Ocean pointe island retreat

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$224

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

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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Price per night from

$372

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

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$287

Oceanfront Oasis with Quintessential Island Living

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 11

“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow waters off of our own private beach was perfect for the kids. Pictures don't do it justice. Plenty of amenities - snorkeling gear, paddle boards, kayaks, pool toys, karaoke machine, portable waterproof sound system, etc. I have been to Florida many times always renting houses. This was by far the best.

Responds fast! avg. 3 hours 40 minutes

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Price per night from

$1,723

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

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Price per night from

$402

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

Studio / 1 bathroom / sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

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Price per night from

$230

Oceanfront Condo at Ocean Pointe Resort

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$259

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$163

Please all towels most be left clean if not will be a fee. Thanks

Lower Keys house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 40 minutes

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Price per night from

$306

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

Sunrise Drive

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

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Price per night from

$198

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

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Price per night from

$197

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$352

Beautiful Private Home with Beach Access.

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$58

Florida Keys Splendor at Hammer Point

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Piece of Paradise” This home was perfect! Midgy was very accomodating. We took the kayak out several times, since it was a 2 person my husband and I could enjoy it together. The bikes that Midgy had were great for fun rides around Hammer Point. We went snorkeling at John Pennekamp Park, it was amazing! A trip to Key West is a must. We used Fury for parasailing and the dolphin adventure, they were very professional and fun tour guides. I would highly recomend this rental it surpassed all expectations!

Responds fast! avg. 57 minutes

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Price per night from

$115

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$1,805

House on 7th ST in KEY Colony Beach W/CABANA CLUB

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$214

Tropical 3-level, End-unit Condo With 3 Bedrooms, 3 Bathrooms Water View#

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$287

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 33 minutes

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Price per night from

$309

Comfortable Clean HouseBoat in an amazing location

Tavernier boathouse

1 bedroom / 2 bathrooms / sleeps 5

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Price per night from

$345

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

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

“Just what the family needed” The accommodations were just what we needed. Chris was a gracious host; she was available for anything we needed. The location and amenities fit our needs perfectly. We were able to swim and kayak in the channel, hang out in the tiki hut, play cards and share meals in the large kitchen. We were close enough to family members, restaurants, and attractions. The trip to Key West wasn't too bad either. Overall, a perfect rental!

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Price per night from

$516

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$373

Key Colony Beach Griffins' Getaway

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$345

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 23 minutes

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Price per night from

$173

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

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Price per night from

$271

The Banyan Resort at Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Wonderful week at The Banyan Resort!!” My husband and I recently stayed in a 2 bedroom/1Bath unit at The Banyan Resort and we were extremely pleased with everything!! Everyone we encountered from the front desk, housekeeping, grounds personnel and other guests were warm and welcoming! The unit was very spacious and comfortable and you can"t beat the location. It's within walking distance of all attractions and Fort Zachary Taylor State Park. The owner was very responsive to all of my questions and a pleasure to work with and we look forward to being repeat guests at The Banyan Resort.

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Price per night from

$263

Conch Key Villas Unit 2 Spectacular open water views!

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$190

New Listing Family Friendly

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 32 minutes

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Price per night from

$367

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$460

Now booking Spring/Summer 2020! Dock, Bikes, Kayak, 2 beach clubs

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Paradise Found” This is an adorable property. It is so "keysie"! The decor is just lovely with all the amenities you need. The kitchen is fully equipped, there was a new set of pots and pans, crockpot, blender and anything else I needed. The grill looked new, was clean and just waiting for our catch! The beds were very comfortable. The unit was immaculate. One could easily while away the day just sitting on the comfortable patio, or on the adirondack chairs at the dock and watch a variety of wildlife (birds, fish, manatee, lizards), and also watch the boats going up and down this clean canal. Don't get so busy that your forget to spend an afternoon at the Cabana Club and Inch Beach. They are not to be missed. , We rode the beach cruisers every day. Just needed a few more hours in each day. Oh! Don't forget to watch the spectacular sunset at Sunset Park! Dee, the owner is a dream to work with, full of suggestions and information, and returned our deposit in a timely manner. You will not be disappointed in this property, and believe me, you won't want to leave!

Responds fast! avg. 33 minutes

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Price per night from

$165

Paradise in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$287

Walk or Bike!! Truman Annex: 3 BIKES, 2 PORCHES, A POOL, WIFI, & PARKING

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 47 minutes

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Price per night from

$204

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

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