Search 105,200+ Vacation Rentals

Grassy Key Vacation Rentals & Homes - 40 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

40 Vacation rentals near Grassy Key

Your search has been expanded 8.9 miles to include more rentals

(12)

1 / 30

Marathon House - 0.7 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house had everything we needed. There are 2 King bedrooms and a twin bedroom on 2nd floor. We would have liked a tv in the twin room but there was no cable in ther. Down stairs ther was a king suite with jacuzzi tub and across from that room was...”
- Review left on 05/02/2016

$471

Very Good (12 reviews)

Inquire

from $471 / night

(14)

1 / 18

Marathon Villa - 0.7 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our second time staying here. It's a great location, very comfortable and well-equipped house and so peaceful. The owner is great to work with. Can't wait to stay here again...”
- Review left on 01/09/2017

$286

Excellent (14 reviews)

Inquire

from $286 / night

(11)

1 / 16

Marathon House - 0.7 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“When we found this rental online, we knew it was what we were looking for. Very private, quiet and peaceful. As other reviewers have said, really nice house, but could be amazing. Many items in rental are dated, a few found not to work properly. We...”
- Review left on 03/13/2017

$315

Very Good (11 reviews)

Inquire

from $315 / night

(5)

1 / 15

Marathon Cottage - 0.7 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Nice place. Could use a little maintenance. The shower heads were awful and the kitchen trash can was all broken up. Also used very cheap trash bags. And the blender didn't work”
- Review left on 03/04/2017

$413

Very Good (5 reviews)

Inquire

from $413 / night

(3)

1 / 31

Marathon House - 1 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Stayed with my family of 5. Plenty of room, great spot. Would recommend. Check pics, they are true to the rental...”
- Review left on 03/18/2017

$428

Very Good (3 reviews)

Inquire

from $428 / night

(18)

1 / 26

Marathon House - 1.2 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

$372

Excellent (18 reviews)

Inquire

from $372 / night

1 / 24

Duck Key Villa - 4.5 miles away

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $536 / night

1 / 24

Duck Key Villa - 4.5 miles away

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

from $340 / night

(10)

1 / 28

Marathon House - 6.3 miles away

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“# families, 8 kids ranging from 2-14yrs stayed here for a week. Absolutely could not be happier! Pool was fantastic and warm, hot tub was well maintained, and clean. Grounds were breathtakingly beautiful. Kyaks were readily available, and easy to get...”
- Review left on 01/19/2017

$415

Very Good (10 reviews)

Inquire

from $415 / night

(1)

1 / 43

Marathon House - 6.4 miles away

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“This place is absolutely AMAZING! We stayed here with 3 families and we had plenty of room. Everything from the beautifully maintained grounds to the spacious house made this stay amazing! The views of the sunsets from the balcony were outstanding....”
- Review left on 10/01/2016

$300

Excellent (1 reviews)

Inquire

from $300 / night

(8)

1 / 8

Marathon House - 6.4 miles away

  • 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

$244

Excellent (8 reviews)

Inquire

from $244 / night

(4)

1 / 32

Marathon Houseboat - 6.4 miles away

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

$428

Very Good (4 reviews)

Book

from $428 / night

(7)

1 / 15

Marathon Condo - 6.4 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This condo was perfect for us. The owner was very attentive to our requests. The dishwasher quit working and within an hour or so the repair man was there and the dishwasher was fixed. Lots of little extras were evident, lights and shelves at bedside...”
- Review left on 01/05/2016

$284

Very Good (7 reviews)

Inquire

from $284 / night

(26)

1 / 36

Marathon House - 6.8 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were looking for a place to get away from the fast pace world. This place was a perfect fit. While the villas could use some updates, we spent most of time at the pool or the private beach. We visit the Keys every year for a quick weekend...”
- Review left on 07/02/2016

$151

Very Good (26 reviews)

Inquire

from $151 / night

(15)

1 / 11

Conch Key Cottage - 7.3 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Air conditioning

$243

Excellent (15 reviews)

Book

from $243 / night

(9)

1 / 16

Conch Key Cottage - 7.3 miles away

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

$185

Excellent (9 reviews)

Book

from $185 / night

1 / 19

Key Colony Beach House - 7.4 miles away

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

from $180 / night

(7)

1 / 8

Key Colony Beach Condo - 7.4 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We truly enjoyed every minute of this beautiful condo in Key Colony Beach for the month of March, 2015. From the decor to the amazing views from the balcony, we were so happy with all the amenities. The kitchen was well equipped with everything we...”
- Review left on 04/05/2015

$160

Excellent (7 reviews)

Inquire

from $160 / night

1 / 24

Marathon Condo - 7.5 miles away

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

from $200 / night

(3)

1 / 16

Marathon Condo - 7.6 miles away

  • 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

$177

Very Good (3 reviews)

Inquire

from $177 / night

(1)

1 / 24

Marathon House - 7.7 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$257

Excellent (1 reviews)

Inquire

from $257 / night

(3)

1 / 21

Marathon Villa - 7.7 miles away

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house was amazing and so was Cindy! I almost hate to let the rest of the world know what a gem this property is. We booked the home with another couple and unfortunately our friend's father became terminally ill and ended up passing away during...”
- Review left on 01/26/2017

$321

Excellent (3 reviews)

Inquire

from $321 / night

1 / 51

Key Colony Beach House - 7.8 miles away

  • 7
  • 16
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $572 / night

1 / 23

Marathon Townhouse - 7.8 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$245

Book

from $245 / night

(3)

1 / 42

Marathon House - 7.9 miles away

  • 8
  • 20
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“The house was great, plenty of parking, great location, plenty of space, beds were much nicer than expected. Access to the Vaca Cut for fishing either Gulf or Atlantic was great. Main complaint was no water or electric to the dock to clean your...”
- Review left on 06/20/2016

$542

Very Good (3 reviews)

Book

from $542 / night

(15)

1 / 29

Marathon House - 7.9 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$257

Very Good (15 reviews)

Book

from $257 / night

(1)

1 / 18

Marathon House - 7.9 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

$357

Excellent (1 reviews)

Book

from $357 / night

(2)

1 / 31

Marathon House - 7.9 miles away

  • 12
  • 30
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$798

Excellent (2 reviews)

Book

from $798 / night

(6)

1 / 27

Marathon House - 7.9 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$285

Very Good (6 reviews)

Book

from $285 / night

(1)

1 / 22

Marathon House - 7.9 miles away

  • 4
  • 18
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“My family and extended family enjoyed room to relax, plenty of things to do (fishing, kayaking, snorkeling, and scuba diving), room enough to enjoy the serenity of peace and quiet, the luxury of easy access to shore, and exploring all the native...”
- Review left on 07/13/2015

$799

Very Good (1 reviews)

Book

from $799 / night

(1)

1 / 20

Key Colony Beach Condo - 8 miles away

  • 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

$104

Excellent (1 reviews)

Inquire

from $104 / night

(2)

1 / 34

Key Colony Beach House - 8.1 miles away

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Wonderful house and plenty of space for our party of 14. Pool was wonderful and everyone was very comfortable...”
- Review left on 07/26/2016

$629

Very Good (2 reviews)

Inquire

from $629 / night

1 / 24

Marathon Villa - 8.3 miles away

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

from $200 / night

1 / 30

Marathon House - 8.4 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $428 / night

(18)

1 / 44

Marathon Townhouse - 8.4 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We enjoyed our stay at Indigo Reef Villa 29. It was exactly what was depicted. Beautiful accommodations and the view was fantastic. Everyone we met was very nice...”
- Review left on 02/16/2016

$215

Excellent (18 reviews)

Inquire

from $215 / night

(11)

1 / 51

Marathon House - 8.5 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“We have been Lucky enough to get Married at Seabird Key in 2005 & have been going back for our Anniversary ever since. It is truly amazing place away from everything . It is very well kept outside & Inside .very clean. It is beautiful & worth every...”
- Review left on 03/18/2016

$900

Excellent (11 reviews)

Book

from $900 / night

(4)

1 / 34

Marathon Villa - 8.7 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This nicely renovated unit was a great location, close to Key West, Bahia Honda, and walking distance to the 7 mile bridge. Snorkeling, jet skis and parasailing right around the corner, as well as many restaurants. The only amenities we would have...”
- Review left on 06/03/2015

$144

Excellent (4 reviews)

Inquire

from $144 / night

1 / 22

Marathon House - 8.8 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

$143

Book

from $143 / night

(12)

1 / 18

Marathon House - 8.9 miles away

  • 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 (12 reviews)

Inquire

from $257 / night

(9)

1 / 12

Marathon Shores House - 8.9 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
“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

$358

Very Good (9 reviews)

Inquire

from $358 / night