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Grassy Key Rentals

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248 Houses

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$252

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

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 29 minutes

Price per night from

$566

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

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 47 minutes

Price per night from

$115

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$229

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Price per night from

$252

Glamping in the Florida Keys

Grassy Key caravan/mobile home

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$184

Great rentals within 20 miles that match your search

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 21 minutes

Price per night from

$189

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

$235

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$242

Key Colony Beach FL - Cay Condo

Key Colony Beach condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$229

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

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

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

$974

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

Conch Key Villas Unit 2 Spectacular open water views!

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 21 minutes

Price per night from

$189

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

Marathon Shores townhouse

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$331

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 21 minutes

Price per night from

$674

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

$997

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

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$119

Breezy Palms

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 5 minutes

Price per night from

$744

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$227

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$122

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 9 minutes

Price per night from

$189

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

Price per night from

$269

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

$490

Paraidise with or witout boat

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 25 minutes

Price per night from

$316

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. 31 minutes

Price per night from

$167

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Price per night from

$197

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 33 minutes

Price per night from

$216

Breeze Swept

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$220

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

Price per night from

$661

Large Home near Beach & Key West

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 3 hours 10 minutes

Price per night from

$439

Couple's Getaway! Design King Unit, Pool, Parking, Marina! Close to Attractions

Marathon Shores apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$207

Ultimate Florida Keys Escape! Elegant Unit for 4 Guests, Pool, Parking, Marina

Marathon Shores apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$207

REDUCED RATES!!! Two Design Units for 8 Guests, Pool, Tennis, Parking, Marina

Marathon Shores apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$404

Group Getaway! Three Modern Units for 12 Guests, Pool, Parking, Marina

Marathon Shores apartment

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$577

Active Rare Find! Four Chic Units for 16 Guests, Pool, Parking, Tennis

Marathon Shores apartment

4 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$808

Kokomo Cove Boat House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

Price per night from

$188

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rentals in Grassy Key

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