Search 105,200+ Vacation Rentals

Florida Keys Waterfront Vacation Rentals, House Rentals & More - 197 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

197 Vacation rentals

Filters applied: Waterfront

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$245

Book

from $245 / night

(17)

1 / 15

Key Largo House

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We stayed for five days. Two families with five small children. The house was perfect! There are toddler beds tucked into 2 large walk in closets. There were two cribs and a high chair. They even had baby spoons! There is an adorable pirate ship...”
- Review left on 03/03/2016

$450

Very Good (17 reviews)

Book

from $450 / night

(11)

1 / 16

Key Largo Villa

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The Condo was very spacious, clean and very well presented. With a family, we appreciated the room and comfy beds! The washer and dryer were an added bonus. We liked the location and really enjoyed our stay. We wish it was longer and would love...”
- Review left on 12/06/2016

$175

Excellent (11 reviews)

Book

from $175 / night

(45)

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“we were very pleased with our stay at Alamar. We actually were the only ones on the property that weekend. It was quiet and very tranquil. I recommend this hidden little gem. We brought our two dogs and on Saturday rode down to the Islandmorada Fish...”
- Review left on 10/12/2016

$200

Very Good (45 reviews)

Book

from $200 / night

(13)

1 / 19

Conch Key Cottage

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$175

Excellent (13 reviews)

Book

from $175 / night

(17)

1 / 11

Conch Key Cottage

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

$150

Excellent (17 reviews)

Book

from $150 / night

1 / 24

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

from $199 / night

(3)

1 / 15

Tavernier House

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We have just returned from a month long celebration of retirement in the Keys. The lovely home we stayed in was perfectly located smack dab in the middle of everything there is to do in the Keys! The owner of this property was quick to respond to...”
- Review left on 02/05/2016

$134

Excellent (3 reviews)

Inquire

from $134 / night

(4)

1 / 20

Summerland Key House

  • 4
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house was great. Had everything you could ask for. The owner even called to make sure we made it ok and if we needed anything. Best view, plenty of space absolutely gorgeous couldn't of asked for better...”
- Review left on 08/19/2014

$233

Excellent (4 reviews)

Inquire

from $233 / night

(39)

1 / 10

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were very pleasantly surprised at the location of this rental. We loved the view of the sunrises over the water. The home was very adequately supplied with all kitchen utensils. Grill outside had plenty of gas. They had fresh flowers to please...”
- Review left on 02/25/2017

$157

Very Good (39 reviews)

Inquire

from $157 / night

(3)

1 / 15

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“Had a fantastic time at the Gulfpointe condo in Marathon, FL. The location was great, the condo was spacious and had all the items needed to make our trip memorable for our family of three. The pool is great - spent a lot of time there. Beaches in...”
- Review left on 04/09/2015

$171

Very Good (3 reviews)

Inquire

from $171 / night

(123)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$210

Excellent (123 reviews)

Book

from $210 / night

1 / 17

Islamorada Townhouse

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $200 / night

(8)

1 / 8

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“It could not have been better. The owners were excellent, and the home had everything imaginable. We will be back...”
- Review left on 12/25/2016

$243

Excellent (8 reviews)

Inquire

from $243 / night

(9)

1 / 15

Marathon Shores House

  • 4
  • 8
  • 7 nights min
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
“Great place to stay, owner easy to reach and help if needed. Great dock for your boat, easy to park tie up and launch. House very clean and felt like home, I plan to stay there again”
- Review left on 01/06/2016

$343

Very Good (9 reviews)

Inquire

from $343 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$457

Very Good (48 reviews)

Book

from $457 / night

(6)

1 / 14

Islamorada House

  • 3
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This home was amazing for our family! The owners are amazing and beyond accommodating!! Make sure when you book this place you have plenty of time to rest and really enjoy what it has to offer. We enjoyed endless hours in the Tikki Hut eating fresh...”
- Review left on 07/10/2017

$214

Excellent (6 reviews)

Book

from $214 / night

(2)

1 / 18

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house was perfect for our laid back group. The rooms and kitchen were clean and well stocked with supplies. We had a wonderful time and will be back! Heather”
- Review left on 07/05/2017

$143

Very Good (2 reviews)

Inquire

from $143 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

Book

from $295 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property...”
- Review left on 08/05/2016

$420

Excellent (9 reviews)

Book

from $420 / night

1 / 22

Marathon Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $171 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Very Good (7 reviews)

Book

from $250 / night

1 / 24

Key Largo Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$155

Book

from $155 / night

1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $340 / night

1 / 24

Marathon Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $200 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$200

Excellent (17 reviews)

Inquire

from $200 / night

1 / 25

Marathon House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $350 / night

(11)

1 / 18

Marathon House

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“It was a great place to stay. Very nice and clean. Location is great. Neighbors are friendly. For the fisherman, this place is great. Caught several fish. Would definitely refer this place to others. Look forward to coming back...”
- Review left on 11/03/2016

$257

Very Good (11 reviews)

Inquire

from $257 / night

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”
- Review left on 05/29/2015

$429

Excellent (7 reviews)

Book

from $429 / night

(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

$358

Excellent (1 reviews)

Book

from $358 / night

(2)

1 / 23

Cudjoe Key House

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$173

Very Good (2 reviews)

Inquire

from $173 / night

(53)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (53 reviews)

Book

from $209 / night

(1)

1 / 34

Key Largo House

  • 4
  • 14
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Thank you for letting us use your home for our family vacation. We enjoyed every part of it. Used the kayaks several times, used the pool 24/7 and really enjoyed the out doors. We brought our boat and we managed to get in and out of the narrow canal...”
- Review left on 07/20/2015

$200

Excellent (1 reviews)

Inquire

from $200 / night

(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house and lush landscaping are beautiful! We enjoyed the pool so much. The private dock is a great touch even though we don't have a boat. We would recommend this property highly! Quaint restaurants in Marathon have some great food, too! We...”
- Review left on 11/03/2014

$393

Excellent (11 reviews)

Inquire

from $393 / night

(3)

1 / 16

Key Largo Apartment

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were in the Tower unit 212 at the Kawama Yacht Club. Norman Wartman met us and gave a tour of the facilities. Norman was very helpful and kept us in stitches with his barrage of jokes. The condo was in very good condition and the kitchen was...”
- Review left on 11/29/2016

$250

Excellent (3 reviews)

Inquire

from $250 / night

(1)

1 / 23

Summerland Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Nice quant house on the canal, with a short distance to either the Atlantic Ocean or The Gulf. Had a great time with Family. Did some site seeing, fishing, diving- snorkeling and enjoyed hanging with Parents, Kids and Grandkids. Had only one...”
- Review left on 08/15/2016

$500

Very Good (1 reviews)

Book

from $500 / night

(15)

1 / 16

Islamorada Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The house was so nice, everything you could possible need. The view from the lanai is superb, Bobbie was a great owner, would answer your call for anything. The complex is quiet, and the people are friendly. What an amazing vacation...”
- Review left on 11/11/2016

$200

Excellent (15 reviews)

Inquire

from $200 / night

1 / 16

Marathon Shores House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Private garden

from $143 / night

(8)

1 / 25

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“This was our third year in Heaven, Living the dream, House is clean as new,great location for boaters easy out to open water,fishing was great this year caught a 300 lb. grouper , weather was warmer this year , lots of calm wind days , more things...”
- Review left on 02/02/2017

$221

Excellent (8 reviews)

Book

from $221 / night

(1)

1 / 20

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great location on the water. Pleasant heated large pool. Small number of units and lots of room on the grounds. Pier and beach. Clean, quiet, and well kept inside and out by owners there. Got an invite to meet for a birthday party and got to...”
- Review left on 02/06/2016

$103

Excellent (1 reviews)

Inquire

from $103 / night