Grassy Key Vacation Rentals

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Vacation Rentals in Grassy Key

Oceanfront Sandy Beach Vacation Rental Unit 1
Private beach

Oceanfront Sandy Beach Vacation Rental Unit 1

9.4 out of 10, Exceptional, (105)
"Such a wonderful location and property. Great for exploring the keys. Very comfortable and nicely decorated. Lovely folded towels at the start of our stay was a beautiful touch. Very quiet and plenty of lovely restaurants and attractions nearby. We would love to stay again! Thank you Wluld"
Oceanfront Sandy Beach Vacation Rental Unit 1
4 Keys To Paradise | 5 Bed, 3.5 Bath
Property grounds

4 Keys To Paradise | 5 Bed, 3.5 Bath

9.6 out of 10, Exceptional, (26)
"The house was large and very clean. We had three families staying with 10 total people and we never felt cramped. Wouldn't hesitate to stay here again."
4 Keys To Paradise | 5 Bed, 3.5 Bath
Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included
Outdoor dining

Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included

9.0 out of 10, Wonderful, (13)
"This is the first vacation for our three blended families. The house was just as the pictures indicated. We were able to kayak from the beach. The house was well stocked and cool when we arrived.we had a wonderful week. It is a great place to stay."
Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included
Beachfront 8-bedroom villa just a short walk to Coco Plum Beach
A heated pool

Beachfront 8-bedroom villa just a short walk to Coco Plum Beach

9.8 out of 10, Exceptional, (87)
"Our family loved this vacation home! It was clean, well stocked kitchen, very responsive property manager. We would love to vacation here again. We loved the pools, fishing pier and many spaces to hangout. "
Beachfront 8-bedroom villa just a short walk to Coco Plum Beach
Skipjack Resort & Marina
Outdoor pool, sun loungers

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1141)
"We love staying at this property because it’s just like an apartment with all the comforts of home."
The price is ￥46,737
￥58,205 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Skipjack Resort & Marina
Aqua Lodge Rentals At Coconut Cay
Front of property

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (126)
"Unique floating accommodations were so nice. Highly recommend this stay."
The price is ￥70,199
￥106,409 total
includes taxes & fees
Dec 27 - Dec 28
Aqua Lodge Rentals At Coconut Cay
Tropical Cottages
Superior Bungalow, Ensuite (Cottage 04) | Exterior

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (755)
"The Cottage made a wonderful stay for a quick getaway. I shared the main cottage with another family and my only complaint is that because the walls are thin, we were awakened by their incessant argument and the constant slamming of their suite and main doors. "
The price is ￥21,727
￥24,444 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Tropical Cottages
Yacht Haven Marina
Standard Bungalow | Living area | 42-inch Smart TV with digital channels, Netflix, Hulu

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (99)
"Excellent value for money."
Yacht Haven Marina
Knight's Key Suites
Outdoor pool, sun loungers

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1069)
"Sits right by the ocean!"
The price is ￥23,290
￥29,563 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Knight's Key Suites
Cabins at Bonefish Bay
Exclusive Cabin | Living area | Flat-screen TV

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (23)
"Nice place to stay. "
Cabins at Bonefish Bay
Sunshine Key RV Resort & Marina
Sundeck

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (141)
"Nice place to relax"
Sunshine Key RV Resort & Marina
PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
On the beach, sun loungers

PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

9.6 out of 10, Exceptional, (38)
"The property is right on a beach, although the beach is not great. Small and it was muddy and weedy when we were there, but it might have been due to the waves. The bungalow was clean and spacious. The only draw back is that the bathrooms are located upstairs and you have to climb circular stairs."
PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
Fridge, microwave, oven, stovetop

Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view

9.6 out of 10, Exceptional, (10)
"We had a great stay. The house and property were clean and tidy. The house was well stocked with appropriate amenities. "
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa
A heated pool

Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa

9.6 out of 10, Exceptional, (66)
"Clean, comfortable, well-equipped kitchen. Perfect for our 2nd girls getaway at this property. We will be back! Thank you, Debbie. "
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Private beach, sun loungers, beach towels

One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

10.0 out of 10, Exceptional, (189)
"Excellent vacation spot. Would love to come back in the future!"
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
The BeachComer ~ Paradise in the Florida Keys!
Beach towels

The BeachComer ~ Paradise in the Florida Keys!

9.8 out of 10, Exceptional, (247)
"Even though we started our stay with a few bumps, the owner made it right immediately! We are grateful for that! The house was very nice and spacious!"
The BeachComer ~ Paradise in the Florida Keys!
Soulshine Cottage- Close to everything you need in Marathon
Aerial view

Soulshine Cottage- Close to everything you need in Marathon

9.8 out of 10, Exceptional, (19)
"I was only there for work, so I didn't see the sights or use the hot tub. However, the house was very comfy, and the host was attentive to everything. Having a stocked kitchen and a laundry room made the stay very enjoyable. Thank you. "
Soulshine Cottage- Close to everything you need in Marathon
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
A heated pool

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

8.8 out of 10, Excellent, (221)
"Wonderful well appointed villa save no ice cube trays in freezer. National support was rude and of no help."
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Canal Front Pool Home with Dockage, Jetted Pool, Tiki Hut, 2 Kayaks & 2 Bikes!
Beach nearby, beach towels

Canal Front Pool Home with Dockage, Jetted Pool, Tiki Hut, 2 Kayaks & 2 Bikes!

10.0 out of 10, Exceptional, (44)
"David so so very helpful. The location is perfect for grocery shopping and just far enough away from Key West to make it an ideal place to relax and have fun. Good job you guys. I will definitely be back soon. Dr Jim"
Canal Front Pool Home with Dockage, Jetted Pool, Tiki Hut, 2 Kayaks & 2 Bikes!
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
Property grounds

Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty

9.8 out of 10, Exceptional, (57)
"This place is very relaxing. Owners are very nice. We will stay again!"
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
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
Signature Suite, 2 Bedrooms, Oceanfront | View from room

Rainbow Bend Resort

2.5 star property
8.2 out of 10, Very Good, (543)
"This was our second time stayingnat this resort. Good location close to town but out of the business. Its very quiet with its own beach area. We would for sure stay here again when staying in Marathon "
The price is ￥29,550
￥46,530 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Rainbow Bend Resort
Gulf View Waterfront Resort
Exterior

Gulf View Waterfront Resort

2.5 star property
8.6 out of 10, Excellent, (393)
"Absolutely loved it!! Room is great with kitchen and back door to access the swings! Pool is heated. Laundry available. Very highly recommend! "
The price is ￥30,809
￥34,660 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Gulf View Waterfront Resort
Grassy Flats Resort & Beach Club
Exterior

Grassy Flats Resort & Beach Club

2.5 star property
9.4 out of 10, Exceptional, (216)
"We loved the property's options for things to do—paddleboarding, kayaking, multiple water sports, and bikes. The pools are very nice and relaxing. The room we had was spectacular and had an ocean view. The Rhum House had delicious food. It was overall a great experience and we hope to return soon."
The price is ￥70,163
￥78,932 total
includes taxes & fees
Jan 12 - Jan 13, 2025
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.