Raccoon Key Vacation Rentals

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Vacation Rentals in Raccoon Key

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is $216
$369 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
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A heated pool
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
10.0 out of 10, Exceptional, (54)
"My husband and I really enjoyed our time at Scarlet Mango Inn! Communication with the hosts was super easy with the convenience of reaching them via text. Our room was very clean and the property was so cute! It was a little noisy in the morning as staff cleaned outside, otherwise it was quiet. There is plenty to do within walking distance - food, bars, shopping, etc. We would definitely stay here again!"
The price is $168
$377 total
includes taxes & fees
May 29 - May 30
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Interior
The Crystalmarine Suite – Rustic Luxury on the Sea
10.0 out of 10, Exceptional, (1)
"This was such a nice and cozy place to spend the weekend! We took our boat from key largo and docked up next to the houseboat and it was just amazing! I live how you can order food delivered to your door! It had tons of privacy and if your wondering no it does not move a lot at night! The solid pannel powered everything at night and we slept very peaceful! The sunsets from this house boat are 2nd to none would stay here again in the future!"
The price is $550
$698 total
includes taxes & fees
May 28 - May 29
The Crystalmarine Suite – Rustic Luxury on the Sea
Pool
Bahama Village studio @ the Galleria!
10.0 out of 10, Exceptional, (5)
"It was very clean and nice. The air conditioning worked great. Located close to Duval. The only issue we had was that there was no closet or place to put clothes so after a few days it was hard to keep organized."
Bahama Village studio @ the Galleria!
Fridge, microwave, oven, stovetop
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
10.0 out of 10, Exceptional, (75)
"The boat was clean and comfortable for our 3 night stay. The staff was top notch."
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (191)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is $699
$1,520 total
includes taxes & fees
May 23 - May 24
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (102)
"Beautiful property in a great location. I would definitely stay again."
The price is $131
$290 total
includes taxes & fees
May 29 - May 30
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Pool | Outdoor pool, a heated pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (104)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (203)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is $350
$444 total
includes taxes & fees
May 29 - May 30
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Beach nearby
Unique Home with loft @ Truman Annex
9.8 out of 10, Exceptional, (103)
"It was great from start to finish. The property was and is perfect everything you could need right there at your fingertips. Property is close to the pool which was super nice. Nice walking distance to a lot of places to eat drink or shop Close to activities Highly recommended"
Unique Home with loft @ Truman Annex
Aerial view
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
9.6 out of 10, Exceptional, (80)
"Great place for a group to hang out in Key West"
The price is $1,699
$3,414 total
includes taxes & fees
May 23 - May 24
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is $99
$240 total
includes taxes & fees
May 30 - May 31
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach nearby
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (158)
"In the center of it all."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Interior
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 135..ngt + ex
9.6 out of 10, Exceptional, (186)
"We spent a week in Key West at this nice little main floor one bedroom suite. The location is great, and walkable to anywhere you might want to go in Key West. Parking was pretty easy...always found a spot within a 1/2 block. The area is safe and quiet, but really easy to get to all the great sites and the beaches. If you are considering a trip to Key West, Marilyn's place is a great place to stay. Thank you, Marilyn for having us!"
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 135..ngt + ex
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (199)
"Close to everything but just far enough away to be quiet and relaxing. Cute little house. Very walkable location."
The price is $432
$811 total
includes taxes & fees
May 25 - May 26
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Don't see what you're looking for?
See all available properties in Raccoon Key
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.

Raccoon Key Vacation Rental Travel Info

Popular accommodation
Raccoon Key private vacation homes
International airport
Key West, FL (EYW-Key West Intl.)

Other types of properties in Raccoon Key you may be interested in

View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1508)
"Great views of the pools, water and marina. Out of the way from downtown Key West but just as convenient with the hourly shuttles, & restaurant on site. The staff was great, friendly and accommodating. We’ll be back! "
The price is $175
$255 total
includes taxes & fees
May 27 - May 28
Oceans Edge Key West Resort, Hotel & Marina
Outdoor pool, sun loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1451)
"We enjoyed our stay at Havana Cabana! Loved the pool and the atmosphere!"
The price is $183
$270 total
includes taxes & fees
Jun 10 - Jun 11
Havana Cabana at Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1761)
"Great and professional staff."
The price is $272
$370 total
includes taxes & fees
Jun 5 - Jun 6
Margaritaville Beach House Key West
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.

Everything you need to know about Raccoon Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Raccoon Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Raccoon Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Raccoon Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Raccoon Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Raccoon Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $99 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Raccoon Key rentals

At Expedia, we put the best Raccoon Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Raccoon Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Raccoon Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Raccoon Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Raccoon Key properties
Expedia verified reviews

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

5/5 Excellent
"Great views of the pools, water and marina. Out of the way from downtown Key West but just as convenient with the hourly shuttles, & restaurant on site. The staff was great, friendly and accommodating. We’ll be back! "
A verified traveler stayed at Oceans Edge Key West Resort, Hotel & Marina
Posted 11 hours ago
Oceans Edge Key West Resort, Hotel & Marina