See all properties

Helluva Happy Place

Helluva Happy Place House in Key West

Helluva Happy Place House in Key West

Helluva Happy Place House in Key West

Helluva Happy Place House in Key West

Helluva Happy Place House in Key West

Don't miss out! Price and availability may change

House in Key West, FL

6 guests · 3 bedrooms · 2 baths

Reasons to book

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Includes essentialsOutdoor Cooking and more

About this house rental

Helluva Happy Place offers accommodations in Key West, 1.1 miles from Mallory Dock and 1.1 miles from Mallory Square. The air-conditioned accommodation is a 4-minute walk from Southernmost Point.

Amenities at Helluva Happy Place

Non-smoking

Outdoor Cooking

Fire alarm

Fire extinguisher

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

$$$$

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Helluva Happy Place. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Helluva Happy Place pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Helluva Happy Place?

We found 4 amenities for this rental. This includes non-smoking, outdoor cooking, fire alarm, and fire extinguisher.

Explore similar stays in Key West

Explore all stays

Angel Fish Cove | Updated Townhome Retreat Near Duval

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

Enjoy the best of Key West in our House, Angel Fish Cove | Updated Townhome Retreat Near Duval. A stunning property with amenities including Air conditioning, Dryer and WiFi/Internet, and more.

10.0 / 10.0

Outstanding(39 Ratings)

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

6 guests · 3 bedrooms · 2 baths

This House in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! | Month Long Stays Only

6 guests · 2 bedrooms

Free WiFi/internet · Air conditioning · Pool

Indulge in a peaceful retreat at Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! | Month Long Stays Only, our elegant House in Key West. Enjoy amenities including Free WiFi/internet, Towels and Linens, and more.

A LATITUDE ADJUSTMENT

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Pool · Beach access

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at A LATITUDE ADJUSTMENT for $339 for your next trip.

9.6 / 10.0

Outstanding(48 Ratings)

TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for the perfect place to call home during your trip to Key West? This House offers a comfort and style with top-notch amenities, including Air conditioning, Balcony/Terrace and Dryer, and more.

9.4 / 10.0

Outstanding(48 Ratings)

TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Nestled in Key West, this House is perfect for your next vacation. Enjoy TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!'s top-rated amenities, including Air conditioning, Balcony/Terrace and Dryer, and more.

10.0 / 10.0

Outstanding(6 Ratings)

Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

Enjoy the best of Key West in our House, Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking. A stunning property with amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

10.0 / 10.0

Outstanding(42 Ratings)

**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.

6 guests · 2 bedrooms · 2 baths

When traveling to Key West, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $316 per night.

8.8 / 10.0

Excellent(37 Ratings)

A License to Chill in the Truman Annex, Key West

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

Looking for a memorable stay in Key West? Our House might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more during your stay.

9.8 / 10.0

Outstanding(43 Ratings)

**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…

6 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $301 per night for your next great vacation.

You can save with One Key

9.9 / 10.0

Outstanding(104 Ratings)

**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at **VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES... for $310 for your next trip.

10.0 / 10.0

Outstanding(6 Ratings)

Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

When traveling to Key West, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $302 per night.

9.2 / 10.0

Outstanding(36 Ratings)

Poolside Hangover at The Truman Annex in Key West

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a memorable stay in Key West? Our Apartment might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more during your stay.

10.0 / 10.0

Outstanding(52 Ratings)

**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Looking to create some memories in Key West? Look no further than our Apartment, **PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES.... Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.

9.6 / 10.0

Outstanding(133 Ratings)

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

6 guests · 2 bedrooms · 1 bath

Looking for a memorable stay in Key West? Our Apartment might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

10.0 / 10.0

Outstanding(101 Ratings)

**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Soak up the beauty of Key West in our House, **VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.... With a range of amenities such as No pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Bahamian Reed by AvantStay | Walk to Everything! w/ Community Pool | Month Long Stays Only

6 guests · 2 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our House in Key West has everything you need for a rejuvenating stay. Treat yourself to Bahamian Reed by AvantStay | Walk to Everything! w/ Community Pool | Month Long Stays Only's exceptional amenities, such as Free WiFi/internet, Towels and Parking Available.

PELICAN'S PERCH

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet

Looking to create some memories in Key West? Look no further than our House, PELICAN'S PERCH. Enjoy top-rated amenities including Free Parking, Non-smoking and WiFi/Internet, and more.

9.8 / 10.0

Outstanding(37 Ratings)

MAI TAI TERRACE - KEY WEST

6 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Indulge in a peaceful retreat at MAI TAI TERRACE - KEY WEST, our elegant Apartment in Key West. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

9.8 / 10.0

Outstanding(53 Ratings)

**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...

6 guests · 2 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our House in Key West has everything you need for a rejuvenating stay. Treat yourself to **SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...'s exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

You can save with One Key

9.4 / 10.0

Outstanding(48 Ratings)

Colorful Cocktail in the Truman Annex

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

This Apartment in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

9.8 / 10.0

Outstanding(9 Ratings)

Gulf Getaway | Condo w/Pool!

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

Looking for a memorable stay in Key West? Our House might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more during your stay.

9.0 / 10.0

Outstanding(2 Ratings)

Dog-friendly house + guesthouse with private hot tub - less than a mile to beach

8 guests · 4 bedrooms · 3 baths

Indulge in a peaceful retreat at Dog-friendly house + guesthouse with private hot tub - less than a mile to beach, our elegant House in Key West. Enjoy amenities including Pets allowed and Family friendly, and more.

10.0 / 10.0

Outstanding(29 Ratings)

SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!

6 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our House in Key West has everything you need for a rejuvenating stay. Treat yourself to SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!'s exceptional amenities, such as Air conditioning, Balcony/Terrace and Dryer.

You can save with One Key

8.0 / 10.0

Excellent(1 Rating)

Pet Friendly / Hot Tub / Close to Everything

8 guests · 4 bedrooms · 3 baths

When traveling to Key West, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $275 per night.

9.4 / 10.0

Outstanding(204 Ratings)

Hands-Down Best Deal in Key West!

6 guests · 2 bedrooms · 1 bath

WiFi/Internet · Air conditioning · Pool

This inviting Apartment in Key West can fit your needs for many types of vacations, at $300 per night.

You can save with One Key

7.0 / 10.0

Good(4 Ratings)

THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

The best choice in Key West for House, for $307 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.8 / 10.0

Outstanding(37 Ratings)

MAI TAI TERRACE - KEY WEST

6 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $300 per night for your next great vacation.

9.6 / 10.0

Outstanding(7 Ratings)

Villa 3 Bdrms/3 baths/close to everything/off st prking/Old Town/15% off July

7 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a Villa in Key West, this Villa for $287 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

7.0 / 10.0

Good(4 Ratings)

THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking to create some memories in Key West? Look no further than our House, THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!. Enjoy top-rated amenities including Air conditioning, Dryer and WiFi/Internet, and more.