Keys Holiday Rentals

(40 rentals)
Keys Holiday Rentals
23
We manage privately owned single family homes and condos. Established in 2007 we have grown due to our reputation for guest satisfaction and enjoy repeat business. The properties we represent are clean and offer a variety of amenities in a variety of price ranges.
booking message booking message

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Founder's

$643

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

MINIMUM STAY: 7 Nights SATURDAY TO SATURDAY The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. ...

View all property information

Property Type

Islamorada House

"Awesome"

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

View all property information

Property Type

Islamorada Condo

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Anne's Beach

$169

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

View all property information

Property Type

Islamorada House

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

View all property information

Property Type

Islamorada Apartment

Show less

4 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to beach: 3 miles to Founders Park Beach

$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 1 Month"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family ...

View all property information

Property Type

Tavernier House

"Wow - Beyond Amazing"

This was our first visit to the Keys so what we knew before coming to the area was learned through internet searches and friends. The website for Conch Bar South is nicely done, but certainly can’t convey ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$217

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days"Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier ...

View all property information

Property Type

Tavernier House

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

MINIMUM STAY: 28 Nights. NEW OWNERS are in the process of making a number of renovations to this unit. Posted photos will be updated as soon as the renovations are completed – by August 2022. The anticipated date for completion is AUGUST 2022. Here is a partial list of planned improvements ...

View all property information

Property Type

Key Largo Townhome

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...

View all property information

Property Type

Islamorada House

Show less

6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

MINIMUM RENTAL: 7 NIGHTS This is a lush tropical setting in a gated compound located directly on Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There’s a “sunning” area with lounge chairs on the peninsula so you can capture ...

View all property information

Property Type

Islamorada Estate

Show less

$382

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

MINIMUM STAY: One Month Delightful vacation home located in the popular Islamorada neighborhood of Port Antigua. You will love this charming and cozy home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. From the main living area sliding doors open into the ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Minimum Rental: 1 Month This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave. The interior is bright, fresh and ...

View all property information

Property Type

Islamorada Condo

"Paradise"

We just loved staying in this beautiful condo for a month. This place has everything you need to enjoy your stay. Just bring clothes.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to everything - restaurants, ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days "Plantation Adventure" is a sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious ...

View all property information

Property Type

Plantation Key House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days "Palm Harbor" is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd ...

View all property information

Property Type

Plantation Key House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS “Beacon Reef 301” is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has all the comforts ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

View all property information

Property Type

Islamorada Condo

"Great Location"

We love the Keys and this is central to all fishing and restaurant locations While going to keys we love the area

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...

View all property information

Property Type

Islamorada Cottage

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 1 Month Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo with screened balcony overlooking views of the tropical complex and of course the beautiful ocean. While the owners attend to their other property "up north" ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Minimum Rental: 7 Days (Saturday to Saturday)"Brock Haus on the Gulf" is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open ...

View all property information

Property Type

Plantation Key Condo

"Late October stay in Brock Haus."

It was great to be back in Islamorada last week. Beautiful view from Brock Haus so we didn't do much but enjoy the waterfront and being on the Gulf up close. The common pool is good sized and we used that ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 7 miles to Founders

$112

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

NEW LISTING Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in the morning ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Minimum Rental: 7 Nights Saturday to Saturday"Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry ...

View all property information

Property Type

Key Largo Condo

"Very Nice place to stay"

Very nice condo. Conveniently located in Key Largo. They gave you all you need, toliet paper, dish soap, dishwasher soap, and laundry soap! Plus many other things! More than enough room for us, we had ...

See all reviews

Show less

5 BR | 3 BA | Sleeps 12 | Quick View

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

MINIMUM STAY: 28 DAYS ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. Sandglass is a four-unit condo complex located on Lower Matecumbe in Islamorada. This unit offers 180 degree ocean views and is situated on a large lagoon which ...

View all property information

Property Type

Islamorada Condo

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

$267

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Ready for occupancy this winter! This is a very special single family home with many amenities. Relax on the open porch and watch the boats come and go from the marina and keep an eye on your boat at the same time. Spend your Keys holiday in this upscale Venetian Shores single family home conveniently ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

View all property information

Property Type

Islamorada Condo

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

MINIMUM STAY: 1 Month Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and ...

View all property information

Property Type

Islamorada Condo

"Stunning"

My stay at the Palms has been one of my best vacations. The views, the fishing, the pool and great people. The condo was simply gorgeous , fully stocked and the people were oh so nice. I cant wait to ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

3

$162

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen

About this property

Minimum Rental: 28 Days "Beacon Reef 310" is located in one of the most desirable condominium complexes in the Upper Keys. New owners have updated the kitchen and added new furnishings. This condo complex is convenient to everything - restaurants, fishing, diving, snorkeling, swim with ...

View all property information

Property Type

Islamorada Condo

"Great stay."

Clean, well equipped, phenomenal views, and friendly residents. Realty staff was very helpful and responsive to any issues that came up. Great spot for kids as well, and very close to many top restaurants.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people ...

View all property information

Property Type

Islamorada House

"Great time!"

We had a wonderful time at Sunshine Place. The accommodations were far above our expectations. I know this is crazy but you have clean comfortable white sheets, great pillows and a comfortable bed! The ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

MINIMUM STAY: One Month Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely remodeled in 2021 with all new everything. Walls were moved to enhance the work flow. At the end of the kitchen there is a computer ...

View all property information

Property Type

Plantation Key Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

MINIMUM STAY: 30 DAYS This condo offers breathtaking oceanfront views. Imagine watching the sun rise as you lay comfortably in your bed or have your morning beverage on the balcony and enjoy watching the fishing boats leave for their day's adventure. You'll be able to see cruise ships as they ...

View all property information

Property Type

Key Largo Condo

"Beautiful location stunning home."

Beautifully decorated and fabulous location! I highly recommend this home. We had a great time and wonderful experience here in Key Largo FL.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

MINIMUM STAY: 28 DAYS This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's preference. Dine in the ...

View all property information

Property Type

Islamorada Condo

"a wonderful place."

beacon reef #503 was a great condo. We really enjoyed our month stay . The grounds were so well maintained and also the condo.We already booked for next year ! Cant wait till then. Lauren Mccrae

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Minimum Rental: 28 nightsPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

View all property information

Property Type

Islamorada House

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$81

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

MINIMUM RENTAL: 1 Month The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. ...

View all property information

Property Type

Islamorada Condo

"Great condo!"

This was a great location to watch beautiful sunrises. The facilities were as described. The condo was super clean and up to date.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 – granite counters, stainless steel appliances, and ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

View all property information

Property Type

Islamorada Condo

Show less

Map
Expand map Close map
 Vacation Rentals