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Islamorada Rentals with Pools

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204 house rentals in Islamorada with pools

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

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Price per night from

$1,227

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restaurants. The porch offers lovely sunrises, and peaceful enjoyment of the waterway view and harbor. The pool is heated and quiet. The owners were very helpful with our questions. We would definitely stay at this property again, and recommend it to others!

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Price per night from

$221

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$208

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,760

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

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Price per night from

$170

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$430

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 39 minutes

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Price per night from

$1,438

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$356

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 47 minutes

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Price per night from

$173

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$356

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$114

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

“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. 1 hour 3 minutes

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Price per night from

$2,290

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$87

$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and really nicely decorated. There were some beach chairs on the balcony that we used at the beach which was nice to have since we had flown to Florida. There were also beach towels to use. The kitchen was cute with everything you would need to cook, although we mainly just ate breakfast there. It is located away from traffic so nice and quiet. I swam in the pool once and it was warm like a bathtub. Felt good after a day at the beach. This was our first trip to the Keys, and I liked that we were centrally located. We were a couple hours from Fort Lauderdale where we flew in from, and a couple hours from Key West where we went for a day trip. We loved John Pennekamp State Park which is only about 20 minutes away, and swam with a manatee at Canon Beach. We also snorkeled with Robbie's in Islamorada which is 20 min. the other way from us. I would definitely stay there again if I return to the keys.

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$128

Islamorada Paradise

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$711

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 42 minutes

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Price per night from

$626

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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$263

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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Price per night from

$192

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodeled and it has everything you would need for a great Keys vacation. Futura Yacht club has a big heated pool, tennis courts and if you are a boater a great marina with its own boat ramp which made it easy for us to enjoy our boat and jet ski's. It is a gated complex with security, centrally located to all the activities & restaurants in the area. We found the owner most helpful, accommodating and easy to deal with. We are looking forward to our next stay!!

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Price per night from

$206

152 Valencia Drive

Islamorada house

4 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$267

THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 41 minutes

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Price per night from

$163

BROCK HAUS ON THE GULF

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset every day. We also brought our boat and the dock is literally right across the condo and ocean access is not too far away by water. Manatees visited the dock about every day, you can see picture below. We looked at other condo options and by far this was the best that suited our needs. The service provided was excellent. They were a phone call away if we needed anything. We will definitely be staying here again. Thank you so much!

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$212

PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter would roll down and the room was completely dark. Talk about sleeping well! As for the complex, everyone was very friendly and we made some very good friends. The pool was heated and the hot tub was always warm and enjoyable. We have already made plans to go back next year. If you have the chance to rent a unit there, GO, you will not be sorry.

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Price per night from

$81

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$101

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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$385

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

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$330

Beautiful Bayside View with Swimming Pool

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 43 minutes

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$822

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$318

THE PALMS 405 - 93

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$121

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$620

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$148

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$81

Windy Cove #3

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$172

Experience the Florida Keys like never before!!!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

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$253

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$1,066

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$111

BLUE WATER RETREAT

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Blue Water = Everything that you want” This place delivers. You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working with Keys Holiday Rentals was a very good experience. Would definitely recommend and will visit again.

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Price per night from

$184

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$164

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