A dolphin swimming near a wooden dock and a tree branch in the water.

Grassy Key Luxury Vacations

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What to do in Grassy Key

Marathon: Rhum Runner Aqua Park Adventure

$38

per adult

0% of travelers recommend

Day Sailing Adventure in the Florida Marine Sanctuary

$120

per adult

100% of travelers recommend

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Top Luxury Grassy Key Hotels

Grassy Flats Resort & Beach Club

A wooden deck with a pool and chairs overlooking a beach with palm trees.

Address: 58182 Overseas Hwy, Marathon, FL, 33050, US
Location: 0.2 mi from Grassy Key
Star rating: 4/5
Guest rating: 9.4/10 (Exceptional, 505 reviews)
Price: $247 nightly, $278 total, Dec 13 - Dec 14, Total with taxes and fees, for Top Luxury Grassy Key Hotels
Review: Excellent all around

Rainbow Bend Resort

A table with breakfast items and a view of the beach.

Address: 57784 Overseas Hwy, Marathon, FL, 33050, US
Location: 0.6 mi from Grassy Key
Star rating: 2.5/5
Guest rating: 8.2/10 (Very good, 1000 reviews)
Price: $149 nightly, $168 total, Nov 15 - Nov 16, Total with taxes and fees, for Top Luxury Grassy Key Hotels
Review: just what we needed for couple nights stay

Gulf View Waterfront Resort

A tropical resort with a swimming pool, palm trees, and a view of the ocean.

Address: 58743 OVERSEAS HWY, Marathon, FL, 33050, US
Location: 0.3 mi from Grassy Key
Star rating: 2.5/5
Guest rating: 8.4/10 (Very good, 645 reviews)
Price: $98 nightly, $110 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Luxury Grassy Key Hotels
Review: Room is simple but clean and everything is there what might be needed.

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

A pool area with lounge chairs and a view of the ocean.

Address: Marathon, FL, US
Location: 0.9 mi from Grassy Key
Guest rating: 9.2/10 (Wonderful, 66 reviews)
Price: $1,111 nightly, $1,234 total, Nov 13 - Nov 14, Total with taxes and fees, for Top Luxury Grassy Key Hotels
Review: "We had a great week at this property and ultimately gave it 5 stars because it delivered exactly what we needed: an unbeatable location, beautiful water views, and a convenient home base for exploring the Keys.The biggest strengths are definitely the setting and location. The views are fantastic, and Grassy Key was a great central location for day trips both north and south. We spent most of our time out exploring, on the water, or enjoying the area, so having an affordable waterfront place to...

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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All you need to know about luxury vacations in Grassy Key

What can I expect from a luxury Grassy Key vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Grassy Key vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.

How can I find all-inclusive luxury vacation packages in Grassy Key?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.

Can I book a cheap Grassy Key luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at . Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Grassy Key?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.

Can I book a package in Grassy Key with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.

How can I find the best luxury vacation deals in Grassy Key?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Grassy Key with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.

Why should I book my luxury trip to Grassy Key with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.