Holiday Homes in Grassy Key

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Featured Holiday Homes in Grassy Key

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

5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.

10.0 out of 10, Exceptional, (69)
"Great time with friends for the week. House was clean, pool and hot tub were amazing and the location was perfect !!! "
5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.

Villa Coral, brand new, spectacular outdoor area!

9.8 out of 10, Exceptional, (24)
"Awesome stay! Very responsive to some changes we requested when we checked in. Is completely as advertised and would highly recommend!"
Villa Coral, brand new, spectacular outdoor area!

"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage

10.0 out of 10, Exceptional, (228)
"Quick responses from the host. Great location and home has lots to offer!"
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage

Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await

9.8 out of 10, Exceptional, (17)
"Excellent stay"
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await

Blue Island Marathon!

10.0 out of 10, Exceptional, (11)
"This gouse was an absolute gem.Will absolutely return for future vacations."
Blue Island Marathon!

DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!

10.0 out of 10, Exceptional, (25)
"Had a amazing time Villa was amazing , great location Everything was as stated , had no issues at all Host replied to any queries super quick Thanks again "
DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!

Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets

"Great stay, great property, super comfortable.With 2 boys, the bunk beds were perfect!"
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets

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.

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

Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!

10.0 out of 10, Exceptional, (157)
"The house was very nice. A quiet retreat for the week. We even had a chance to see a manatee in the canal. "
Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!

Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!

9.6 out of 10, Exceptional, (26)
"Stayed here for 2 weeks with friends renting the other side. planned on doing more excursions but staying here with the pool, hot tub, and tiki bar, and being on the water we were content just to enjoy all the amenities! The hosts were very helpful if we had any questions. Would gladly book again."
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!

Waterfront home perfect for fishing, water sport, fam fun in Marathon FL keys

10.0 out of 10, Exceptional, (66)
"House was really nice. The Pool was amazing. We were in it a few times a day. Great location, close to everything."
Waterfront home perfect for fishing, water sport, fam fun in Marathon FL keys

Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak

9.6 out of 10, Exceptional, (88)
"Very nice place but road is tight if you have a big boat 24' and entry to canal is very shallow at low tide"
Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak

Best 2/2 in KCB. Private Pool/Private Dock/Lush backyard/Tiki & Outdoor Bar.

9.8 out of 10, Exceptional, (112)
"Our stay at Southern Comfort was excellent! The backyard outdoor space is a dream! Communication with the property owner/manager was easy and they quickly responded to all of our questions! Very enjoyable vacation. "
Best 2/2 in KCB. Private Pool/Private Dock/Lush backyard/Tiki & Outdoor Bar.

Open Ocean View, Private Hot Tub, Ice Machine, Moor 26' Boat!

10.0 out of 10, Exceptional, (11)
"Beautiful home, everything is updated. We enjoyed our stay here. Right on the water so it was nice to sit outside in the morning and have coffee.Close to everything you you want.Would definitely stay here again!"
Open Ocean View, Private Hot Tub, Ice Machine, Moor 26' Boat!

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.

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

Sale!! Rates have been Discounted 16% off remaining July days! Coral Lagoon #13

10.0 out of 10, Exceptional, (258)
"I took my sons fishing in Marathon and wanted a nice place to stay. This house was perfect - clean, convenient, and comfortable. I would stay there again and highly recommend it. "
Sale!! Rates have been Discounted 16% off remaining July days! Coral Lagoon #13

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

9.4 out of 10, Exceptional, (70)
"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
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