Holiday Rentals in Grassy Key

April 2025

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May 2025

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Holiday Rentals in Grassy Key

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

9.2 out of 10, Wonderful, (40)
"Most an amazing place, with an amazing view. Frank was great to work with if had any questions or needs. We have been coming down to Marathon for 10 years and had one place we rented be sold, this was our first year at this location. So private, pool was amazing, kitchen had everything you need, all bedrooms had own bathroom, screen porch had unreal views. We will definitely be back next year and hopefully many years in the future. A little piece of heaven on earth."
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

Sunsets in Paradise~ Gulf Front Pool Home, 22' Dock, Kayaks, Bikes & Paddleboards

9.0 out of 10, Wonderful, (24)
"Great property with great views."
Sunsets in Paradise~ Gulf Front Pool Home, 22' Dock, Kayaks, Bikes & Paddleboards

Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

8.6 out of 10, Excellent, (9)
"Great times , house was stocked , we enjoyed our time here . The house is not new but suited our wants / needs just fine . Our boat is 34’ overall length….. plenty of room . Marina 7-7 close , about 3 miles to ocean access via the long bridge on way to this property. Quite community , a definite do over . Thanks"
Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

🌇 Ocean Sunset Views with Pool and Dock 🌇

9.0 out of 10, Wonderful, (37)
"It was peaceful "
🌇 Ocean Sunset Views with Pool and Dock 🌇

Morton Manor: Updated 9-Bed, 7.5-Bath Estate with Private Pool, Pickleball, Tiki

10.0 out of 10, Exceptional, (2)
"We cannot recommend this place enough! There were 15 of us staying here and everyone loved it. We cooked large meals in the perfectly appointed kitchen while taking in the exquisite views. The activities available on this property are amazing and we all thoroughly enjoyed them: ping-pong, pickle ball, basketball, putting on the green, swimming, paddle-boarding and fishing to name a few...there's something for everyone. Our boys love to fish and they caught (and released) barracuda, parrot...
Morton Manor: Updated 9-Bed, 7.5-Bath Estate with Private Pool, Pickleball, Tiki

Waterfront Beauty 8-guests, Dock, Kayaks and more

10.0 out of 10, Exceptional, (7)
"The house was spotless and it had lots of amenities including kitchen supplies and outdoor furniture. Of course, the highlights are the breathtaking views plus the pool and it was so lovely to have a dock exclusively for us."
Waterfront Beauty 8-guests, Dock, Kayaks and more

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1179)
"Mid way thru the Keys was a plus. It's off season, but everything was very good, and we see that they are working to make the experience even better for the busy season. We'd definitely stay again!"
The price is €248
includes taxes & fees
30 Apr - 1 May
Skipjack Resort & Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (805)
"It was verry cozy!"
The price is €119
includes taxes & fees
30 Apr - 1 May
Tropical Cottages

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (138)
"Perfect location, plenty of attractions close by. "
The price is €257
includes taxes & fees
4 May - 5 May
Yacht Haven Marina

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.2 out of 10, Very good, (31)
"The view is incredible "
The price is €252
includes taxes & fees
20 May - 21 May
Aqua Lodges at 47th Street Gulfside

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (42)
"Nice place I would stay there anytime "
Cabins at Bonefish Bay

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1109)
"Nice place"
The price is €126
includes taxes & fees
5 May - 6 May
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (159)
"Truly enjoyed our time in such a unique experience. "
The price is €276
includes taxes & fees
30 Apr - 1 May
Aqua Lodge Rentals At Coconut Cay

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

9.4 out of 10, Exceptional, (47)
"Beautiful condo, nicely decorated. Elevator to use, has a roof top table and chairs to relax and get all the sun you need. Has a smaller pool but nice "
PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!

9.6 out of 10, Exceptional, (120)
"Enjoyed our time in Marathon, the property was very nice. We only needed 4 of the bedrooms and did not use the bunk bed room which is great as the room is directly off the master suite. If we had small children "
LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

10.0 out of 10, Exceptional, (254)
"We enjoyed the location of the home. We could walk to a some bars/restaurants which is always a plus. The home was very clean and comfortable. The hosts were always very responsive when we had questions - thanks."
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

The Reef at Marathon, Florida Keys

4.0 star property
8.8 out of 10, Excellent, (5)
"The Reef was a great place to stay. The Villa was wonderful. The pool was great. Staff very friendly. I highly recommend this place. "
The Reef at Marathon, Florida Keys

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

10.0 out of 10, Exceptional, (87)
"This was a much needed break! Dragon fly lite was absolutely perfect in every way. Jerry and Barbie were great at communicating. I enjoyed the peaceful vibe, the pool area is incredible!"
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Great Water Front 2 Story Townhouse With Boat Slip available at additional cost

8.6 out of 10, Excellent, (41)
"The kitchen had ample supplies. We were there during the coldest and windiest week of the year. The heat didn’t work so it got pretty cool. We didn’t use the the deck much since it was so cool. The condo is on a canal but a fence blocks the view and access is not allowed. The small tub was not heated so we could not use that. Other than that the condo accomodated 2 couples well. We enjoyed visiting the dolphin research center nearby and would have enjoyed it more if the weather was nicer. There...
Great Water Front 2 Story Townhouse With Boat Slip available at additional cost
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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Other types of properties in Grassy Key you may be interested in

Rainbow Bend Resort

2.5 star property
8.2 out of 10, Very good, (620)
"The rooms are very nice, and very clean"
The price is €148
includes taxes & fees
30 Apr - 1 May
Rainbow Bend Resort

Gulf View Waterfront Resort

2.5 star property
8.6 out of 10, Excellent, (454)
"Nice quiet place to stay for your home base of Marathon."
The price is €151
includes taxes & fees
1 May - 2 May
Gulf View Waterfront Resort

Grassy Flats Resort & Beach Club

2.5 star property
9.4 out of 10, Exceptional, (274)
"very nice resort with good food, drinks and surroundings"
The price is €355
includes taxes & fees
20 May - 21 May
Grassy Flats Resort & Beach Club
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.