Deals on vacations and trips to Raccoon Key

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Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,776, price is now $1,170 per person
$1,170
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This bed & breakfast features an outdoor pool and a rooftop terrace. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, luggage storage, and concierge services are also on offer.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,960, price is now $1,954 per person
$1,954
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,351, price is now $2,278 per person
$2,278
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,687, price is now $3,410 per person
$3,410
per person
Dec 1 - Dec 7
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,159, price is now $3,051 per person
$3,051
per person
Dec 1 - Dec 7
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.

Top Raccoon Key hotels deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$225 nightly
The price is $253 total per night
$253 total
Sep 28 - Sep 29
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $180 total per night
$180 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$234 nightly
The price is $263 total per night
$263 total
Oct 4 - Oct 5
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $146 total per night
$146 total
Sep 21 - Sep 22
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $197 total per night
$197 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$308 nightly
The price is $346 total per night
$346 total
Sep 28 - Sep 29
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
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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.

Frequently asked questions

How much are vacation packages to Raccoon Key?
Starting at just $1,170, flight and hotel packages are an ideal way to make your travel budget stretch further. Watch out Raccoon Key — here you come!
Where can I get the best vacation package deals for Raccoon Key?
It's difficult to beat Travelocity when it comes to crafting your Raccoon Key package deal. There are as many as 400 air carriers and 1,000,000 worldwide properties to choose from. Book your trip now and get ready to tick another amazing destination off your list.
Why should I purchase my Raccoon Key vacation package via Travelocity?
Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.
Can I save on my Raccoon Key car rental if I book it with hotels and flights?
Combining your flight, hotel and car into a Raccoon Key vacation package is a great way to score an amazing deal. Plus, having your own wheels gives you the freedom to make your way to all those amazing sights you're itching to see. Located 110 mi from Raccoon Key, Zoo Miami is one attraction that should have a place on your itinerary. Fill up the tank and make a day trip of it.
What is the best time of year to go to Raccoon Key?
You'll be able to avoid the tourist crowds and save cold, hard cash in August, September and October, which are the quietest times for tourism. Peak season months of January, February and July are naturally busier (and more expensive), but there's likely to be more going on around Raccoon Key. Lock in a hotel in and get a lot more bang for your buck. Room rates tend to be higher in .
Which airport is best for Raccoon Key?
Heading to Raccoon Key will see you touching down at Key West Intl. Airport (EYW). It's roughly 2 mi southwest of the downtown area.
Where should I stay when visiting Raccoon Key?
Many travelers opt to check in to the Catamaran with kayak. It's a great base for your Raccoon Key escape.

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