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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Grassy Key Holiday Homes

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

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

10.0 out of 10, Exceptional, (70)
"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.
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)
"We absolutely loved this home. High end touches throughout and all the amenities you could ever need. Wonderful communication from the host. "
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Villa Coral, brand new, spectacular outdoor area!
Pool

Villa Coral, brand new, spectacular outdoor area!

9.8 out of 10, Exceptional, (25)
"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!
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
Fully equipped kitchen with refrigerator, oven, microwave, toaster, and sink.

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

9.8 out of 10, Exceptional, (18)
"Excellent stay"
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
Relax by the serene water's edge, where a tranquil table setting awaits with wine and a view of the marina.

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

10.0 out of 10, Exceptional, (26)
"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
Relax in style with two Adirondack chairs and a charming wooden table, perfect for al fresco dining or unwinding.

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

10.0 out of 10, Exceptional, (2)
"Great stay, great property, super comfortable.With 2 boys, the bunk beds were perfect!"
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

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
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.
Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!
Enjoy a tranquil beach experience with a palm tree, rocky shoreline, and clear blue sea.

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

10.0 out of 10, Exceptional, (159)
"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!
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and a bar area at your fingertips.

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!
Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak
Relax in a shaded outdoor space with a table and chairs, perfect for dining or socializing, and enjoy the soothing sounds of a nearby water feature.

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.
Relax in a tranquil outdoor space with a thatched roof, surrounded by a waterway and marina views.

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

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!
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, (71)
"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
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool
Relax by the pool with ocean views, surrounded by lounge chairs and a dining area.

Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

10.0 out of 10, Exceptional, (30)
"Lovely and Comfortable Setting and House with Beautiful Views --- We loved the convenient ocean and gulf boating access"
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool
Coral Lagoon #13: Pool, Water Views, at Vaca Cut with Gulf & Atlantic Access
Waterfront homes with gabled roofs and porches, surrounded by lush greenery and a calm water body.

Coral Lagoon #13: Pool, Water Views, at Vaca Cut with Gulf & Atlantic Access

10.0 out of 10, Exceptional, (260)
"This property is a really nice choice in Marathon. Very close to beaches, activities, restaurants. The pool on property is really nice. "
Coral Lagoon #13: Pool, Water Views, at Vaca Cut with Gulf & Atlantic Access
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

Rainbow Bend Resort

Rainbow Bend Resort

10/10 Excellent
"The motel was a quiet, nice area. Breakfast was good, cooked to order. "
Justin 3-night trip
Posted 2 days ago
Rainbow Bend Resort