Raccoon Key Romantic Vacations

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Top Romantic vacation packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,226

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,321 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$1,972

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

The Marker Resort. This place is one of the best places to stay in Key West! Great Location to everything we like to do. One of the swimming pools were closed for the week but highly recommend this resort.

Reviewed on Oct 19, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,633

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,411

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$2,074

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

Liked the bungalow, smaller but functional. The only problem I had was the air conditioning couldn’t cool the room efficiently and had to keep emptying the dehumidifier. Love the location, pool and hotel.

Reviewed on Oct 17, 2026

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3 Night Romantic vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,173

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,669

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,273

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Reviewed on Oct 19, 2026

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4 Night Romantic vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

Orchid Key Inn - Adults Only

Old Town Key West

$1,028

per person

Nov 22 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,478

per person

Nov 22 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (563 reviews)

Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

$3,304

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (1 review)

Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!

Reviewed on Jul 26, 2026

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How can I find the best Raccoon Key vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Raccoon Key romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Raccoon Key?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Raccoon Key?

Put a price on love with stunning deals for duos starting at just $1,028. Prices and availability are subject to change. Additional terms may apply.

Can I book Raccoon Key spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Raccoon Key?

To book a loved-up break in Raccoon Key, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Raccoon Key with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Raccoon Key romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?