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Pigeon Key Rentals

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295 Results

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295 Houses

NEW LISTING! Comfy retreat w/ separate cottage, patio, & pier

Pigeon Key house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 minutes

Price per night from

$157

NEW LISTING! Cozy home w/ community boat ramp, walk to bay, near attractions

Pigeon Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$137

Canal front home w/ Gulf views, WiFi, balcony, access to open water - dogs ok!

Pigeon Key house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 51 minutes

Price per night from

$157

Sunny home w/ firepit, private pool, private gas grill, & tiki bar!

Pigeon Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$119

NEW LISTING! Dog-friendly oasis with pier, multiple living spaces & water views!

Pigeon Key house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 minutes

Price per night from

$306

Dog-friendly house w/dock & cleaning station - near canals & parks

Pigeon Key house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$141

Charming & inviting beachside getaway w/ free Wi Fi-near dive shops & marina

Pigeon Key house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 minutes

Price per night from

$76

FISHERMANS PARADISE IN THE MIDDLE KEYS1

Pigeon Key house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$202

Two-story waterfront house w/water views, dock, central AC, free WiFi - Dogs ok!

Pigeon Key house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 3 minutes

Price per night from

$228

Great rentals within 20 miles that match your search

Price per night from

$128

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$179

Waterfront Home In Florida Keys

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Relaxing atmosphere.” The house is great. Very clean, comfortable and cozy. As fishermen, we especially loved the location due to the easy access to Gulf. The only problem we had was the weather!! Definitely recommend this home!!

Price per night from

$214

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$358

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$586

Waterfront Property Ocean Side 60' of dockage

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$257

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$166

Discover the Charm of Island Living

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$963

Premier Condo in Upper Florida Keys

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$275

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$90

MM88 Best Keys Location Tranquil Wooded

Tavernier house

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$142

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

Price per night from

$225

Palm Tree Paradise

Tavernier cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$120

$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

Travelers’ Choice award

Price per night from

$139

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$170

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.

Price per night from

$154

The Real Livaboard Experiance. Cruise Inciuded!

Key Largo yacht

3 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$641

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$899

Meagan's Beach House - Bayfront Home with Spectacular Sunrise and Sunsets

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$321

Beautiful Private Home with Beach Access

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

Price per night from

$77

Seas the Day in this Waterfront Home on Oceanside MM90

Tavernier house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$225

1/1 with Living Room plus Oceanview

Tavernier guest house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$162

Keys Townhouse

Tavernier townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

Fabulous and Spacious HOME!!

Ocean Reef house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$163

Islamorada - PARADISE FOUND 3 bedroom/2 bath

Islamorada townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$163

Gorgeous updated Bayview condo

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$184

Relaxation in the Keys! MM 74 1/2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$222

Relaxing Getaway (REDUCED) in Key Largo

Key Largo house

4 bedrooms / 2 bathrooms / sleeps 8

“Awesome! Will stay there again and again.” What a great place in Key Largo. Plenty of room and a great location. Right across from Publix and near all of the fun. We rented a boat from Pennicamp which was a short ride away. This place is perfect for a family. Each kid had their own bedroom and my daughter loved the trundle! There is a boat ramp and beach area that is perfect for relaxing or having a picnic. The owner was so nice and always responded to my questions. Can't wait to go back. We will be adding this to our annual vacation. Way better than a hotel!

Price per night from

$146

Viewing 38 of 295
rentals in Pigeon Key

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