--- title: "Luxury Vacations in Grassy Key 2026 | Expedia.ca" description: "Find incredible offers on Grassy Key Luxury vacations! Plan your next Luxury trip today with Expedia." canonical: "https://www.expedia.ca/lp/theme-vacations/luxury-vacations/3000451823/Grassy-Key" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-12T19:38:10Z --- ![A dolphin swimming near a wooden dock and a tree branch in the water.](https://images.trvl-media.com/place/2437/83757040-1d80-4589-aea2-a5fe1bb3ba0c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Monica Ferro # Grassy Key Luxury Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $4,200 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### What to do in Grassy Key ![Marathon: Rhum Runner Aqua Park Adventure](https://mediaim.expedia.com/localexpert/49181060/0b0d5141-d114-4720-afa3-daa97fdbedd0.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Marathon: Rhum Runner Aqua Park Adventure](https://www.expedia.ca/things-to-do/a.a49181060.activity-details?rid=3000451823) CA $53 per adult 0% of travellers recommend ![Day Sailing Adventure in the Florida Marine Sanctuary](https://mediaim.expedia.com/localexpert/49731974/751c07d5-5a11-4fff-ab3b-e1eaac3f68ed.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Day Sailing Adventure in the Florida Marine Sanctuary](https://www.expedia.ca/things-to-do/a.a49731974.activity-details?rid=3000451823) CA $169 per adult 100% of travellers recommend ![Marathon: Cruisin' Tikis Marathon - Private Sunset Cruise](https://mediaim.expedia.com/localexpert/53074062/d7f67140-b8be-4a0f-9b6a-65976c6e2215.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Marathon: Cruisin' Tikis Marathon - Sunset Cruise](https://www.expedia.ca/things-to-do/a.a53074062.activity-details?rid=3000451823) CA $155 per adult 0% of travellers recommend [See all activities in Grassy Key](https://www.expedia.ca/things-to-do/search?rid=3000451823) ## Top Luxury Grassy Key Hotels ### [Grassy Flats Resort & Beach Club](https://www.expedia.ca/Marathon-Hotels-Grassy-Flats-Resort-Beach-Club.h36881801.Hotel-Information) ![A wooden deck with a bench overlooking a pool area, surrounded by palm trees and a clear blue sky.](https://images.trvl-media.com/lodging/37000000/36890000/36881900/36881801/c3eddccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 58182 Overseas Hwy, Marathon, FL, 33050, US - Location: 0.4 km from Grassy Key - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 505 reviews) - Price: CA $262, CA $363 total, includes taxes & fees, Dec 13 - Dec 14, for Top Luxury Grassy Key Hotels - Review: Excellent all around ### [Rainbow Bend Resort](https://www.expedia.ca/Marathon-Hotels-Rainbow-Bend-Resort.h3863945.Hotel-Information) ![A wooden deck with two chairs and a table, overlooking a beach with palm trees and the ocean.](https://images.trvl-media.com/lodging/4000000/3870000/3864000/3863945/60a631db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 57784 Overseas Hwy, Marathon, FL, 33050, US - Location: 1 km from Grassy Key - Star rating: 2.5/5 - Guest rating: 8.2/10 (Very good, 1000 reviews) - Price: CA $147, CA $229 total, includes taxes & fees, Nov 15 - Nov 16, for Top Luxury Grassy Key Hotels - Review: just what we needed for couple nights stay ### [Gulf View Waterfront Resort](https://www.expedia.ca/Marathon-Hotels-Gulf-View-Waterfront-Resort.h13278553.Hotel-Information) ![A tropical resort with a swimming pool, palm trees, and a view of the ocean.](https://images.trvl-media.com/lodging/14000000/13280000/13278600/13278553/46de1e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 58743 OVERSEAS HWY, Marathon, FL, 33050, US - Location: 0.5 km from Grassy Key - Star rating: 2.5/5 - Guest rating: 8.4/10 (Very good, 645 reviews) - Price: CA $125, CA $141 total, includes taxes & fees, Nov 15 - Nov 16, 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](https://www.expedia.ca/Marathon-Hotels-Private-Oasis-With-Pool-Spa-Dock-And-Ocean-Right-In-Your-Backyard-Allow-Pets.h74876573.Hotel-Information) ![A beach with clear water, a wooden dock, and a palm tree.](https://images.trvl-media.com/lodging/75000000/74880000/74876600/74876573/w1107h730x0y0-77934e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Marathon, FL, US - Location: 1.5 km from Grassy Key - Guest rating: 9.2/10 (Wonderful, 66 reviews) - Price: CA $713, CA $1,779 total, includes taxes & fees, Nov 13 - Nov 14, 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. [See all properties in Grassy Key](https://www.expedia.ca/Hotel-Search?startDate=2026-11-26&endDate=2026-11-27®ionId=3000451823&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Plan the perfect luxury Grassy Key vacation with Expedia ### What are some benefits when booking luxury Grassy Key vacations? When you book a luxury Grassy Key vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. ### How can I find all-inclusive luxury vacations in Grassy Key? If you're looking for something luxurious in Grassy Key, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. ### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from , there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to . After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. ### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Grassy Key. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. ### What should I look for in a luxury family vacation in Grassy Key? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Grassy Key. ### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Grassy Key. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. ### What can help me find the best luxury vacation deals in Grassy Key? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Grassy Key or travelling to more obscure destinations altogether can often lead to lower prices. ### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Grassy Key. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. ### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Vacation Rentals](?equalTargetTab=tab-4) - [Things to do](?equalTargetTab=tab-5) - [Villas in Conch Key](https://www.expedia.ca/Conch-Key-Villas.d3000396828-aaVillas.Travel-Guide-Accommodation) - [Beautiful HOME ON CANAL W/ PRIVATE POOL & FISHING DOCK\~](https://www.expedia.ca/Key-Colony-Beach-Hotels-9TH-ST-BEAUTIFUL-HOME-W-PRIVATE-POOL-ON-CANAL.h21692513.Hotel-Information) - [Canal Front with Cabana Club Privileges! 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