Holiday Homes in Grassy Key

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Grassy Key

The Hammocks at Marathon
Relax by the pool surrounded by palm trees and lounge chairs, with a boat on the water nearby.

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
Exterior

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!
Enjoy cooking in this well-lit kitchen with a large island and oven.

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!
Relax in a serene beachfront setting with a hammock on the pebbled beach, overlooking a marina with boats docked.

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>
Relax by the pool surrounded by palm trees and lounge chairs.

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>
GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~
Enjoy a serene waterfront retreat with a pool overlooking a tranquil canal and lush surroundings.

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.
Enjoy stunning marina views from this property's balcony, featuring a wicker chair and table.

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
Relax by the pool surrounded by palm trees and shaded by green umbrellas.

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!
Relax in a cozy outdoor space with a wicker sofa and marina views.

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
Relax on the tranquil beach with a palm tree and benches for a serene view.

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
Relax by the ocean with a serene beachfront view, a small pool, and shaded palm trees.

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
Relax by the serene pool surrounded by a stone deck and enjoy the tranquil waterfront views.

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
Enjoy a serene beach experience with access to the calm sea and sandy shores.

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.
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!
Relax in a serene outdoor space with a thatched roof, ceiling fan, and string lights, surrounded by wicker furniture and a view of the pool.

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
Relax by the pool surrounded by lounge chairs and umbrellas, with a view of the surrounding palm trees.

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
Enjoy waterfront views from the comfort of your balcony overlooking the marina.

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!
Relax by the pool surrounded by palm trees and a mosaic tile floor.

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
Relax in a tranquil outdoor space surrounded by lush vegetation and a pool.

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
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
Enjoy waterfront views and tranquil surroundings from this serene dock.

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

9.6 out of 10, Exceptional, (19)
"The townhouse has a nice layout, wonderful and relaxing views, was clean, and provided the basic necessities (toilet paper, paper towels, dish and laundry datergent, linens, and 6 beach towels). We would definitely rent this property again. "
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
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

Courtyard by Marriott Faro Blanco Resort

Courtyard by Marriott Faro Blanco Resort

10/10 Excellent
"Cleanness "
Jose 1-night trip
Posted 1 day ago
Courtyard by Marriott Faro Blanco Resort