Holiday Homes in Grassy Key

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Featured Holiday Homes in Grassy Key and around

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"We loved the location of the property and we also loved the entertainment/singer provided by lounge."
The Hammocks at Marathon

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

9.8 out of 10, Exceptional, (48)
"House was spotless, very bright and open! We really enjoyed the pool and even saw a few manatees in the canal! Great location, will be returning next time we’re in the Florida Keys!"
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Vacation with attitude!

10.0 out of 10, Exceptional, (7)
"Good location, family friendly, very nice pool and outdoors. "
Vacation with attitude!

Florida Keys vacation home, Family sized and pet friendly home with a pool!

10.0 out of 10, Exceptional, (19)
"Very clean, welcoming, and just what we needed for our get-away! "
Florida Keys vacation home, Family sized and pet friendly home with a pool!

Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

8.4 out of 10, Very good, (90)
"Well maintained, exceptional location, The management responded immediately to any concern. This was a toughly enjoyable vacation. "
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~

10.0 out of 10, Exceptional, (38)
"Great experience. Would definitely rent again!"
GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~

Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

10.0 out of 10, Exceptional, (8)
"Comfortable place in a nice neighborhood with a beautiful view"
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Palm Villa - Sleeps 6, Boat Slip Available

9.8 out of 10, Exceptional, (138)
"Great trip. Very comfortable for family of 5. Cabana club lovely and great recommendations!"
Palm Villa - Sleeps 6, Boat Slip Available

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

10.0 out of 10, Exceptional, (4)
"We had an amazing stay at this home in Marathon! The property was clean, comfortable, and perfectly set up for a week on the water. Having our boat right at the dock made it so easy to head out fishing or explore the Keys each day. The location was quiet yet close to everything we needed. Highly recommend for anyone looking for a great boating getaway!"
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

9.4 out of 10, Exceptional, (80)
"Weather was great! Answered all my questions quickly"
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

Flipper's Lagoon: 4 BR, 3 BA House in Marathon, Sleeps 10

2.5 star property
9.6 out of 10, Exceptional, (12)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful time at the Flipper Lagoon House. The location is perfect. The house is great. We loved the back patio and the tiki hut near the pool. The tiki hut by the water is a fun place to have an appetizer and watch the sunset. The dock...
Flipper's Lagoon: 4 BR, 3 BA House in Marathon, Sleeps 10

Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon

9.0 out of 10, Wonderful, (27)
"We had a great time fishing off the dock very clean will definitely come back to this place"
Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon

Escape To Marathon in Large 4BR 3BA Canal Front Home Sleep 10 with Heated Pool

9.6 out of 10, Exceptional, (88)
"Host was great and helpful! Beautiful location "
Escape To Marathon in Large 4BR 3BA Canal Front Home Sleep 10 with Heated Pool

Latitude 24! Cabana Club access, deep canal, jacuzzi, kayaks, ice machine.

10.0 out of 10, Exceptional, (12)
"Super cute and nicely updated with perfect layout for a family. Lots of space. Great location with easy check-in/out."
Latitude 24! Cabana Club access, deep canal, jacuzzi, kayaks, ice machine.

New listing in KCB on 11th Street. Perfect for small family vacation home!

9.8 out of 10, Exceptional, (9)
"Excellent location with beautiful patio & pool!"
New listing in KCB on 11th Street. Perfect for small family vacation home!

Key Colony Beach House with Cabana Club Access

2.0 star property
10.0 out of 10, Exceptional, (4)
"We were temporarily relocating away from cold weather and couldn't have asked for a better place to do that. This is by far the best home we've rented over the past decade. Rental contact was super responsive and the home itself was clean and very well appointed. Highly recommend and plan to return!"
Key Colony Beach House with Cabana Club Access

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.4 out of 10, Exceptional, (72)
"Property was great for our group. 2 miles to grocery stores. Pool was great! Used the bikes and had a great time here. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Attention Large Groups! 14Bd/10Bth Home Comfortably Accommodates Up to 30!

9.6 out of 10, Exceptional, (81)
"Melissa was so easy to work with and responded quickly to my messages. The house is fabulous and so much room for the 20 of us ages 11 to 76. The pool was used continually and the pool table and shuffle board were great. I highly recommend the house!"
Attention Large Groups! 14Bd/10Bth Home Comfortably Accommodates Up to 30!

FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

9.6 out of 10, Exceptional, (125)
"House was awesome. everything as advertised and more."
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Grassy Key Hotel Reviews