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Grassy Key Rentals

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281 Houses

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

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 24 minutes

Price per night from

$225

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

Price per night from

$208

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

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 32 minutes

Price per night from

$509

Beachfront Condo with Panoramic Ocean View! Paradise in the Florida Keys!

Grassy Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 12 minutes

Price per night from

$259

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

Price per night from

$202

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

Price per night from

$196

Great rentals within 20 miles that match your search

VACA COVE Waterfront Vacation Home B Sleeps 10 4BR Pool Hot-Tub Dock Family Fun!

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$657

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$296

8c, Efficiency located 50 yards from Ocean

Marathon studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

Price per night from

$195

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$385

Sandy Shore Place 100' Dock, Pool, Kayaks,Sleep 10

Marathon house

4 bedrooms / 2 bathrooms / sleeps 10

“Everything we hoped for!” Service was great, from booking, until the finish of our stay. Place was clean, a little worn, but clean. Our favorite things included the location, right on the beach, and easy access to anything, like stores, restaurants, churches, airport, etc... It is private. The least thing we liked is after a storm the grass all came in and covered the water, but not much can be done about that. We are definitely intending to book again next year. Thank you for a great vacation!

Price per night from

$472

Florida Keys Oceanfront Paradise

Long Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$198

Gulf View Three - 3 bedroom, 3 bathroom, Gulf Side

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Paradise Getaway...” My Husband and I were more than thrilled to take our vacation at the Fisherman's Haven with Dock. Right on the inlet he was able to fish and enjoy the beautiful scenery Fishing license was easy to obtain from the local Kmart just south. We were able to grill out and enjoy eating outside or dine in the beautiful and very accommodating Kitchen which was fully stocked with more than one could need. Everything was very clean.! Having a washing machine was perfect. Beds very comfortable also. We were able to drive to various Keys and enjoyed Key West so much we went twice. Thank You Rent my Island for an a+ and 5 star *** Experience!!! Ps Sharky"s just south on a! has .25 wings and shrimp from 4-6! We will definitely come back!

Price per night from

$439

4BR Waterfront Retreat-Tiki-Jacuzzi-Dock

Marathon Shores house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$387

***NEW 3D Tour Indigo Reef Luxury Villa Exquisite "Latitude Adjustment"! #33

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 39 minutes

Price per night from

$231

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

Marathon house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 8 minutes

Price per night from

$639

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$119

Oceanside retreat , in minutes you can be fishing

Marathon Shores house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$304

Paradise

Key Colony Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$249

Sombrero Beach, canal front home with pool!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

Price per night from

$474

Twin Dolphins on Shelter Bay

Key Colony Beach house

6 bedrooms / 5 bathrooms / sleeps 14

“Better than the pictures!” Vrbo from Homeaway You Have a Review! A new review has been submitted for your property and will be automatically posted within 2 days. The review is displayed at the bottom of this message. We encourage you to submit an owner response to all reviews which will be displayed with the review on the website. Responding to a review gives you an opportunity to make additional comments about your property. Respond Now Review #5651360 Great vacation! I wanted to send an email thanking you and you staff for the help in making this rental possible. We had a wonderful time and the place was amazing. The pictures and description of the place on the website are great but the house is so much more than was described. It was a really big part in making the trip we had amazing. Thank you again for all of your help. We will definitely be going back and hope to be able to use your company in making it happen again. I can't thank you enough. We are still talking about the great time we had and how great he place was. Erik

Price per night from

$443

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

$259

OCEANFRONT LUXURY "Mar Azul"

Marathon house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 2 minutes

Price per night from

$517

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

Price per night from

$326

97% Occupancy Rate, WINTER BOOKING FAST, Private, Breathtaking & Quiet !!

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 30 minutes

Price per night from

$390

Boaters Dream

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$304

Beautiful Waterfront Home Gulf Side W/ Pool, Hot Tub & Kayaks !!!!

Duck Key house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$423

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Price per night from

$203

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 8 minutes

Price per night from

$697

VACA COVE Waterfront Vacation Home F Sleeps 10 4BR Pool Hot-Tub Dock Family Fun!

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 22 minutes

Price per night from

$660

The Seaside Sandpiper

Marathon house

13 bedrooms / 10 bathrooms / sleeps 28

Price per night from

$2,369

Aparment 1

Marathon apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$326

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$212

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

$222

Extraordinary waterfront custom home

Marathon Shores house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$762

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 10 minutes

Price per night from

$158

Conch Key Villas Unit 2 Spectacular open water views!

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 28 minutes

Price per night from

$196

Florida Keys Vacation

Marathon villa

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$711

Viewing 38 of 281
rentals in Grassy Key

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