Grassy Key Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Grassy Key holiday rentals

Outdoor pool

Two Bedroom ADA Suite at Grassy Flats Conch House

Two Bedroom ADA Suite at Grassy Flats Conch House
Marathon
10.0 out of 10, Exceptional, (1 review)
"Incredibly gracious owner and staff"
United States
Michael R.
The price is HK$3,368
HK$4,358 total
includes taxes & fees
16 Feb - 17 Feb
Two Bedroom ADA Suite at Grassy Flats Conch House
Outdoor pool

Three Bedroom Suite at Grassy Flats Conch House

Three Bedroom Suite at Grassy Flats Conch House
Marathon
The price is HK$5,993
HK$7,744 total
includes taxes & fees
26 Feb - 27 Feb
Three Bedroom Suite at Grassy Flats Conch House
Exterior

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (268 reviews)
"Great place. "
Canada
Elizabeth
Yacht Haven Marina
BBQ/picnic Area

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (208 reviews)
"Room was clean, staff was friendly, view from deck was amazing, took the free kayaks out and saw a Manatee, convenient location. Great experience!"
United States
Wendy
Aqua Lodge Rentals At Coconut Cay
Exterior

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (928 reviews)
"Room was great and clean. Had a sweet cat that roamed the premises. Parking is limited to 1 vehicle but that was fine. Definitely would stay there again!"
United States
James
The price is HK$1,946
HK$2,189 total
includes taxes & fees
3 Mar - 4 Mar
Tropical Cottages
Terrace/patio

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.4 out of 10, Exceptional, (10 reviews)
"Nice location, central in Marathon. "
United States
Kris K.
The price is HK$1,231
HK$3,049 total
includes taxes & fees
20 Feb - 21 Feb
Sombrero Beach Tropical Getaway in the Heart of Marathon
Premium bedding, soundproofing, iron/ironing board, free WiFi

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,172 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is HK$1,657
HK$2,032 total
includes taxes & fees
11 Mar - 12 Mar
Knight's Key Suites
Outdoor pool, pool loungers

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,227 reviews)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina
Exterior

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (7 reviews)
"We were the first guests to this villa, Fantastic villa great service from the host and swift response to messages. Amazing location, very clean and tidy, great furniture. Amazing private pool deck. My only negative would be the aircon is very very noisy in the master bedroom. To sum up. Amazing "
United Kingdom
John W.
The price is HK$3,909
HK$7,394 total
includes taxes & fees
7 Mar - 8 Mar
Charming 3-bedroom house featuring a heated private pool.
Smart TV

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"I was disappointed with noise of highway as our building was right across the highway. Beach was also not accessible contrarily to what was said on property description."
Canada
wilma e.
The price is HK$7,194
HK$15,015 total
includes taxes & fees
18 Feb - 19 Feb
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Property grounds

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.2 out of 10, Wonderful, (20 reviews)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
The price is HK$3,275
HK$6,335 total
includes taxes & fees
23 Feb - 24 Feb
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
TV

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (4 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is HK$3,275
HK$6,350 total
includes taxes & fees
2 Mar - 3 Mar
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Property grounds

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (47 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is HK$3,275
HK$6,280 total
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Property grounds

Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (12 reviews)
"Great location, great accomodation, hot tub and patio in the back area was great for relaxing in the evenings."
United States
Justus
The price is HK$2,126
HK$4,994 total
includes taxes & fees
14 Mar - 15 Mar
Seas the Keys Getaway with plunge pool/spa
Smart TV, ping pong

Marina, Pool & Boats with Beautiful Harbor Views

Marina, Pool & Boats with Beautiful Harbor Views
Marathon
The price is HK$3,271
HK$5,565 total
includes taxes & fees
17 Feb - 18 Feb
Marina, Pool & Boats with Beautiful Harbor Views
Interior

Marina View Suite w/ Pool, Tiki Bar & Boats

Marina View Suite w/ Pool, Tiki Bar & Boats
Marathon
The price is HK$3,190
HK$5,453 total
includes taxes & fees
17 Feb - 18 Feb
Marina View Suite w/ Pool, Tiki Bar & Boats
TV

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.6 out of 10, Excellent, (11 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is HK$3,353
HK$6,376 total
includes taxes & fees
10 Mar - 11 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"What a great place to stay in the Key. W had a great time, my wife and two boys who are 20 and 23 lived the Villa. The boys lived the kayaks and we took advantage of walking to our deep sea fishing charter just across the road as well as swimming with the the dolphins at Dolphin a discovery both on Duck Key. Very clean. Beautiful views, great amenitis in the home, just wonderful. Also great to be in the middle of the keys to explore the whole area."
United States
Matt B.
The price is HK$3,119
HK$6,037 total
includes taxes & fees
10 Mar - 11 Mar
Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg
Outdoor dining

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Marathon
9.2 out of 10, Wonderful, (31 reviews)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is HK$3,275
HK$6,335 total
includes taxes & fees
24 Feb - 25 Feb
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (32 reviews)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
The price is HK$3,275
HK$6,280 total
includes taxes & fees
12 Mar - 13 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
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
"Awesome staff, great spot "
Quinton 1-night trip
Posted 4 days ago
Rainbow Bend Resort

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