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Holiday Villas Florida Keys, FL

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$1,075
Per Week
1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Internet Access, Satellite TV & more
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$349
Per Night
1 / 34
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Outdoor Pool, Satellite TV, Dishwasher & more
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$747
Per Night
1 / 15
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5 Bedrooms, 6 Bathrooms, Sleeps 10
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Air Conditioning, Internet Access, Garden & more
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3 Bedrooms, sleeps 8
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3 Bedrooms, sleeps 6
$139 / night
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$496
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Water Views, Air Conditioning, Garden & more
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4 of 5 stars Reviewed 3 January 2012
Renting the houseboat was a unique experience. I was concerned about the logistics of our stay, but we were well instructed on the workings of the houseboat and island, and felt...
4 of 5 stars Reviewed 22 February 2011
If you like semi rustic conditions and loads of privacy, this is the spot! We booked this rental for a week in February for our first "getaway from it all" vacation. Though Key...
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$261
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Outdoor Pool (Heated), Dishwasher, Grill & more
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5 of 5 stars Reviewed 26 October 2014
Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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$1,162
Per Night
1 / 42
6 Bedrooms, 7 Bathrooms, Sleeps 14
Private Outdoor Pool (Heated), Satellite TV, Balcony & more
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5 of 5 stars Reviewed 4 August 2014
What can I say that would do this place justice? Privacy with a gated entrance on famed Millionaire's Row in Key Largo. Or Maybe the spectacular views from all over the...
5 of 5 stars Reviewed 31 December 2013
This luxurious double house is ideal for a large family group. The location is convenient, the houses are spacious and well equipped, the pool and spa are very comfortable, and...
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$331
Per Night
1 / 5
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1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed 18 April 2014
awesome place to stay for lots of relaxation!!! My kids loved it. The place was very clean, nice breakfast. The pool was very clean and warm. the water was perfect.
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$929
Per Night
1 / 34
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Private Outdoor Pool (Unheated), Air Conditioning & more
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5 of 5 stars Reviewed 10 June 2014
This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
5 of 5 stars Reviewed 16 March 2014
My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a group with large quiet bedrooms. The outdoor kitchen and beautiful private...
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$242
Per Night
1 / 11
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Studio, Sleeps 2
Booking
Air Conditioning, Balcony, Internet Access & more
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5 of 5 stars Reviewed 12 November 2014
This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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$20,912
Per Month
1 / 11
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Satellite TV & more
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5 of 5 stars Reviewed 17 June 2013
Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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$128
Per Night
1 / 12
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Studio, 1 Bathroom, Sleeps 2
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$3,485
Per Month
1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 5 December 2013
Loved this place, I will not stay in a hotel again when visiting the keys! Great Price! Excellent Location near to stores, bars, and fun. Just an hour drive to key west and...
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$198
Per Night
1 / 15
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Garden, Grill, Dishwasher & more
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4 of 5 stars Reviewed 25 August 2014
This was our first time staying outside of the known major hotel chains or resorts for vacation thoroughly enjoyed this location. The home is adequately furnished and clean. Also...
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From
$174
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 2
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Satellite TV, Water Views & more
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From
$5,693
Per Week
1 / 29
3 Bedrooms, 3 Bathrooms, Sleeps 8
Private Pool, Water Views, Internet Access & more
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5 of 5 stars Reviewed 23 August 2011
This property is a collection of 4 houses, 2 closer to the ocean, each with their own pool and three bedrooms (Conch and Pelican Houses), the other two behind, with no pool and...
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$174
Per Night
1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Pool, Satellite TV, Grill & more
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4 of 5 stars Reviewed 22 August 2014
Last week we stayed in a 2/2 condo (3207) with our daughter and son-in-law. The condo was very clean and conveniently located in Key Largo. I think they are individually owned...
3 of 5 stars Reviewed 18 August 2014
We stayed at Ocean Point Suites in 2013 unit 3409 and it was fabulous. What a great unit, everything worked, bedroom at the rear facing the Ocean what an experience. In April we...
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$261
Per Night
1 / 15
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4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Balcony, Grill, Internet Access & more
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5 of 5 stars Reviewed 15 June 2014
Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of...
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$243
Per Night
1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 4
Safe, Air Conditioning
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5 of 5 stars Reviewed 9 September 2014
My husband and I had the pleasure of staying here twice! It was perfect for us, we were able to do what we love with ease (i.e. fish and jet ski). The owners were more than...
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$168
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Dryer, Balcony, Satellite TV & more
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From
$581
Per Night
1 / 8
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4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Private Outdoor Pool (Unheated), Internet Access & more
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5 of 5 stars Reviewed 27 August 2014
We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly...
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$662
Per Night
1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Dryer, Grill, Internet Access & more
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5 of 5 stars Reviewed 17 February 2014
For my son's 26th birthday, I wanted to find something special and unusual. This place is amazing! It is very popular, stays booked for most of the year, so you should plan...
4 of 5 stars Reviewed 18 September 2013
Island is about 5 acres located 500 yards from Marathon Florida. The house comes with a boat, kayaks, and fishing equipment. Not to be scared but there are Iguanas on the...
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From
$13,245
Per Month
1 / 44
3 Bedrooms, 3 Bathrooms, Sleeps 6
Internet Access
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5 of 5 stars Reviewed 31 January 2013
My husband and I rented this home for the week of Christmas. We also invited our respective parents. This is the most peaceful home in Islamorada. Centrally located to the upper...
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From
$105
Per Night
1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Dryer, Internet Access, Satellite TV & more
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5 of 5 stars Reviewed 4 August 2014
This is a great little cottage at a very reasonable price. Everything was as described. Just bring your clothes and that's all you need the house is fully stocked with everything...
5 of 5 stars Reviewed 11 May 2014
I wasn't sure what to expect for the price because sometimes pictures are decieving! I was pleasantly surprised. Very homie, clean and close to John PenneKamp park. Not to much...
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From
$2,788
Per Week
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Internet Access, Satellite TV, Water Views & more
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5 of 5 stars Reviewed 29 May 2013
The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for...
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From
$232
Per Night
1 / 32
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Dryer, Washer, Air Conditioning & more
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From
$3,485
Per Month
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 4
Internet Access, Satellite TV, Balcony
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5 of 5 stars Reviewed 14 August 2014
Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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$203
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Dishwasher, Dryer, Internet Access & more
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4 of 5 stars Reviewed 10 June 2014
Very good price for a 2 bed 2 bath in Key West! It Was clean and just what we needed! It was also not right in downtown close to everything so we could get away hen we wanted.
4 of 5 stars Reviewed 24 May 2014
Condo was a great location. Near beaches and activities. Great place to relax. Owner was very courtious. Pool was a little small but the facilities were beautiful.
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$216
Per Night
1 / 8
Studio, 1 Bathroom, Sleeps 2
Internet Access, Grill, Garden & more
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5 of 5 stars Reviewed 11 May 2014
The studio cottage was very clean and quaint (nautical theme) it was a lot newer than we expected it to be, very comfortable and completely equipped we didn’t have to bring...
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$299
Per Night
1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
Internet Access, Grill, Water Views & more
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4 of 5 stars Reviewed 29 April 2014
Comfortable, homey/cozy feeling cottage with the bonus of the daily use of a compact sailboat! A/C, ceiling fans, full kitchen, comfortable queen sized beds, BBQ, porch with fans...
5 of 5 stars Reviewed 10 February 2014
Captain Tom and Peggy's hospitality is second to none! The current managers, Danny and Michele go out of their way to ensure you're comfortable and have everything you need...
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$1,046
Per Night
1 / 47
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3 Bedrooms, 3 Bathrooms, Sleeps 8
Private Beach, Safe, Internet Access & more
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5 of 5 stars Reviewed 24 September 2014
From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from...
5 of 5 stars Reviewed 26 June 2014
This paradise has to be experienced to believe. We have stayed at Seabird Key every year for the last 15 years. Our sons now grown with families of their own, look forward to our...
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From
$165
Per Night
1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 8
Satellite TV, Dryer, Grill & more
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5 of 5 stars Reviewed 13 November 2014
We were surprised to find that property is better than what the pictures show! It's meticulously clean and spacious, with lots of room for about 7 to 8 people. It is literally...
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$290
Per Night
1 / 31
2 Bedrooms, 2 Bathrooms, Sleeps 6
Private Outdoor Pool (Heated), Balcony, Satellite TV & more
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5 of 5 stars Reviewed 27 October 2014
We rented this place in early August this year, two couple and two kids. This place had all the comforts of home, two very nicely appointed bedrooms each with private bathrooms...
5 of 5 stars Reviewed 1 October 2014
We booked this house for our honeymoon. Everything was perfect! Well worth the money. We come to the Keys every year--this has by far been the best experience. We would...
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$407
Per Night
1 / 59
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3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Housekeeping Optional, Washer, Balcony & more
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From
$1,046
Per Night
1 / 25
5 Bedrooms, 4 Bathrooms, Sleeps 12
Private Outdoor Pool (Heated), Fireplace & more
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5 of 5 stars Reviewed 4 September 2014
Our extended family (children, spouses, grandparents) stayed for a week at this beautiful home. We brought our boat (32') and docked it right behind the house. The dock was new...
5 of 5 stars Reviewed 19 July 2014
Beautiful updated house with private beach, kayak, stand up paddleboard, dock for a boat, and perfect sunsets. What could be better
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$203
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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5 of 5 stars Reviewed 28 July 2014
I was looking to rent a house again to enjoy the keys with the family but at the last minute ended up renting this quite and convenient ground level condo that was more than i...
5 of 5 stars Reviewed 2 June 2014
A beautiful location which is on the ground floor, giving you access straight onto the beach. Plenty of furniture to sit and enjoy the wonderful view and very private. The...
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$333
Per Night
1 / 10
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3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Shared Outdoor Pool (Heated), Grill, Washer & more
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5 of 5 stars Reviewed 4 July 2014
This was my second rental through Keys Caribbean . Excellent Price, excellent service, excellent location . A hidden jewel in Marathon.
5 of 5 stars Reviewed 21 June 2014
Best condo we have ever rented Very spacious, well maintained, nicely decorated. Beautiful view, excellent boat dockage. Only complaint: no HD cable for World Cup
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$249
Per Night
1 / 11
1 Bedroom, 1 Bathroom, Sleeps 2
Grill, Water Views, Internet Access & more
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5 of 5 stars Reviewed 16 June 2014
Stayed here for a week in May with a good friend......really cute, clean, apartment looking out over the cove and the boats, palm tree foliage right off the balcony. Easy to get...
5 of 5 stars Reviewed 15 June 2014
This was our best vacation ever with a beautiful, well equipped apartment room and so many interesting things to do. The sailing was perfect for us (with light winds and a very...
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$203
Per Night
1 / 21
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1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
Private Outdoor Pool (Unheated), Washer, Dishwasher & more
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5 of 5 stars Reviewed 16 November 2014
This house was great!!! Don was not only a gracious host but absolutely funny. House is EXACTLY as pictures online show, but better. The location for us was perfect as it was...
5 of 5 stars Reviewed 3 September 2014
This was such a rare find. We will be back and refer our friends. Loved that we had access to the pool. Absolutely the perfect spot!
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$1,162
Per Night
1 / 71
6 Bedrooms, 4 Bathrooms, Sleeps 16
Grill, Dryer, Satellite TV & more
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5 of 5 stars Reviewed 9 October 2014
I've been spending the majority of my birthdays at Shadow Point over the last decade with my favorite people in the world, and my 60th this year was the best so far! Marlee is a...
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From
$157
Per Night
1 / 10
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Satellite TV, Dryer, Air Conditioning & more
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4 of 5 stars Reviewed 8 July 2014
We stayed here 4th of July weekend. The unit itself was nice and clean, pots and dishes were there to prepare breakfast etc. Good size bathroom and living/ dining room area...
4 of 5 stars Reviewed 6 March 2014
Nice older rental in quiet neighborhood. Part of a home that was divided into several units. The unit will sleep up to four since it has a day bed. However, you'll notice in...
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Suitability

  • Wheelchair access (90)
  • Elder access (361)
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  • Pet friendly (272)
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Florida Keys Vacation Rentals

Relaxing in a hammock under a swaying palm tree. Sipping a margarita. Enjoying a cheeseburger in paradise. Life in the Florida Keys is unique, laid-back and fun. Spending your stay in a cramped, sterile hotel room just doesn’t seem to fit the lifestyle. You should consider a vacation rental. We’ll help you find special deals on beach houses, condos, townhouses, cottages and cabins in a variety of settings in Key Largo, Marathon, Islamorada, Big Pine Key and the Lower Keys, Key West and other locales. Better still, you’ll have lots of space to spread out and relax as well as a fully-equipped kitchen where you can fix the perfect margarita.

Florida Keys attractions and activities

From phenomenal scuba diving and snorkeling to world-class ocean sportfishing and flats fishing to eco-tours and sunset watch parties, the Florida Keys has something for everyone. Each section of the Keys has its own unique attractions. In Key Largo, visit John Pennekamp Coral Reef State Park, a spectacular undersea park. In Islamorada, the Theater of the Sea Marine Mammal Park, offers opportunities to swim with dolphins and other creatures. At Marathon’s Crane Point, you can hike through a preserved tropical hardwood grove. In the Lower Keys, beach enthusiasts love the Bahia Honda State Park with its white sandy beaches. Key West is home to the Ernest Hemingway Home and Museum, the Key West Butterfly & Nature Conservatory and Mel Fisher’s Maritime Heritage Museum.

Live like a local in a Florida Keys rental

A vacation rental allows you the freedom to pursue the Florida Keys getaway perfect for you and your family. You’ll have ample space to store your fishing equipment, scuba and snorkeling gear, beach toys and other necessities for a great beach vacation. When it’s time to dine, a fully equipped kitchen allows you to save money and prepare a delicious meal that might even include the big fish you caught earlier in the day. With a vacation rental in the Florida Keys, you can stop imagining what it’s like to live there and actually do it for a short time.

Florida Keys vacation rentals for families

From Key Largo to Key West, we have an inventory of vacation rentals ideal for family getaways. We’ve got plenty of low-cost, budget-helping rentals that will allow you to spend money on things like swimming with dolphins or scuba diving instead of on a pricey hotel room.

Saving money on Florida Keys vacation rentals

Obviously, you want the best deal available to stay within your budget. Whether you want an amenity-rich beachfront estate home, a condo affording stunning sunset views or a cozy cottage or cabin, we have special deals and discounts in every price range.