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Grassy Key Rentals

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244 Houses

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 27 minutes

Price per night from

$567

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 15 minutes

Price per night from

$252

Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 48 minutes

Price per night from

$556

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 15 minutes

Price per night from

$252

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 15 minutes

Price per night from

$229

Glamping in the Florida Keys

Grassy Key caravan/mobile home

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$181

Great rentals within 20 miles that match your search

Florida Keys Fishing & Diving, waterfront Home heated pool, deep dock, parking

Marathon house

4 bedrooms / 5 bathrooms / sleeps 10

“PERFECT multi-family” House was great for us, our kids, and another family. It's a split-living type house, and was PERFECT!!! The pool was very nice, not too small. We spend most of the time on the boat, or in the pool. DEFINITELY recommend this house!!!!

Price per night from

$453

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$324

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$557

RENOVATED 2 BED MARATHON TOWNHOME w/ DOCK SPACE - WALK TO BEACH!

Marathon Shores townhouse

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$342

Palm Cottage - Upscale, 2BR/2BA, Cabana Club Pool

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$234

Florida Keys Beach Home Pool Fishing Diving

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

Price per night from

$237

Key Colony Beach FL - Cay Condo

Key Colony Beach condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$227

Forever Sunset 5bed/3bath open water views with pool & dockage

Marathon house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$613

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$668

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$343

Florida Keys Vacation Villas Waterfront Family Friendly Pool Spa Deep Water Dock

Marathon villa

6 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 41 minutes

Price per night from

$990

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$225

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$240

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$121

Conch Key Villas Unit 2 Spectacular open water views!

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 36 minutes

Price per night from

$188

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 22 minutes

Price per night from

$188

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$117

Key Colony Beach Griffins' Getaway

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$334

A quiet spot in paradise close to fishing with dockage included (#4)

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 21 minutes

Price per night from

$184

House on 7th ST in KEY Colony Beach W/CABANA CLUB

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 36 minutes

Price per night from

$211

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 19 minutes

Price per night from

$151

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$284

Royal Palm House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

Price per night from

$214

Large Home near Beach & Key West

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 13

Price per night from

$431

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 25 minutes

Price per night from

$165

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

Price per night from

$595

CHARMING KEY COLONY BEACH POOL COTTAGE, PVT POOL,46 FT DCK,WIFI

Key Colony Beach cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Most wonderful vacation home ever.” The pool, the hammock, the dock, the decor....it was the best place i have ever stayed. I didnt want to leave. Laying in the hammock every night listening to the palm trees swaying in the breeze. Watching the snook hit the greenies over the underwater light at the dock. Taking a refreshing swim after a long day on the boat. An evening bike ride around key colony. It was everything we wanted on our vacation. And the house was decorated exactly as my own tropical retreat would be decorated, and it is such a comfortable home. I am hoping to come back for 2 weeks next summer.

Price per night from

$234

CARIBBEAN SOUL SAILING CHARTER Bayfront 2 BR cottage w/ 23 foot Sailboat or dock

Conch Key cottage

2 bedrooms / 1 bathroom / sleeps 6

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Price per night from

$324

Price per night from

$397

Waterfront Get Hooked

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“AMAZING” Beyond perfect. Beautiful home, has everything you need. Spotlessly clean. I will be renting again. I would recommend to families and friends to stay.

Price per night from

$348

Paraidise with or witout boat

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 10 minutes

Price per night from

$342

LUXURY HOME WITH DOCK, POOL, HOT TUB, AND ELEVATOR

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“WONDERFUL” Where to start…Larry was at the home when we arrived and took the time to show us everything we needed to know about the systems in the house and how to use the elevator..Daughter and her husband joined us from Wyoming and I must say it was the best vacation we have had…The house is immaculate and we had a wonderful 7 days….We would walk to the top deck and enjoy the sunsets with a fine glass of wine….you could not ask for better views from any where on the property, pool.dock or balconies…We caught fish off the dock, snapper etc….We left with memories that we will never forget…Thanks Larry for sharing your home with us ….It was worth every penny and we hope to visit again…The pool and hot tub was used everyday and they were both relaxing after a hard day… Thanks again, Jim and Mary

Price per night from

$490

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rentals in Grassy Key

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