
House holiday rentals in Key Haven
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Top-rated house rentals in Key Haven
Guests agree: these houses are highly rated for location, cleanliness and more.

Duval Vibes • Pool • 10 Guests
Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

Key West Paradise
Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Gorgeous Romantic Private Villa, Steps from Duval!
Located 20 yards from historic Duval St in the heart of Old Town Key West w/ FREE first-come, first-serve PARKING in front or $10/day. Totally remodeled, beautiful spacious & private 2 story villa sleeps 4 comfortably. New furnishings, free hi-speed wifi, 65" smart tvs, ice machine, electric fireplace in large master suite, lush garden courtyard & shared plunge pool. We provide 2 coffee/tea stations. Walking distance to everything - convenience store, CVS, bars, restaurants & entertainment.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Funky Chicken Cottage with Shared Pool in Paradise
Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Poinciana Treetop ~ Casual Second Floor Duplex
Vacation near historic Duval Street with parking and a treetop view. Or vacation with friends by renting both floors of this duplex. This conveniently located home allows you to have plenty of fun and enjoy a respite in your own private space. THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches.

Octopus's Garden at Coral Hammock
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** OCTOPUS'S GARDEN has been whimsically decorated with furnishings that reflect the laid-back, quirky island life style of Key West.

Gone Coastal
Relax with the whole family at this peaceful place to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral hammock. Enjoy the pool and excellent location on Stock island. Walking distance to Roostica and Hogfish grill. Dogs are welcome but not over 25lbs. Pitsbulls are not allowed by hoa.
Popular amenities for house rentals in Key Haven
House rentals with a pool

Pelican's Roost, Waterfront comfort at Venture Out

Private Parking, Heated Pool - Sweet Caroline

Historic Key West - Cigar House - Sleeps 4

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Ocean Front Home in Great Location

Tropical Island Getaway

Lower Keys Paradise
Weekly house rentals

Charming 2BR | Hot Tub | Deck | W/D

Big Pine Canal Home w/100' Dock

Paradise found

Waterfront FL Keys Cottage @ Venture Out

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

3BR historic home in Old Town, walk everywhere

Betty's Place

Turtle Cove
Private house rentals

Gone Coastal 2

Another Day in Paradise

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

Robinson Crusoe Cottage~ Delight In Island Vibes

Waterfront Anchor House with Boat Basin & Ramp!

Fleming Street 2/1 private home Key West getaway

Butterfly Cottage~ Enjoy hot tub, gourmet kitchen

Margarita Cottage~ Bask In Sunshine by Pool
When is the best time to visit Key Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,014 SGD | $1,206 SGD | $1,639 SGD | $1,324 SGD | $1,278 SGD | $1,085 SGD | $1,368 SGD | $1,549 SGD | $1,091 SGD | $1,141 SGD | $1,377 SGD | $1,185 SGD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about house rentals in Key Haven

Total holiday rentals
Explore 60 holiday rentals in Key Haven

Nightly prices starting at
Key Haven holiday rentals start at $232 SGD per night before taxes and fees

Verified guest reviews
Over 1,180 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Key Haven holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Key Haven rentals

4.9 Average rating
Key Haven stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Luxury rentals Key Haven
- Rentals with a washing machine and dryer Key Haven
- Family-friendly rentals Key Haven
- Waterfront rentals Key Haven
- Rentals with pools Key Haven
- Pet-friendly rentals Key Haven
- Rentals with outdoor seating Key Haven
- Rentals with a patio Key Haven
- Fitness-friendly rentals Key Haven
- House rentals Key West
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- Key West Lighthouse Museum
- Ernest Hemingway Home & Museum
- Sombrero Beach
- Smathers Beach
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Calusa Beach & Loggerhead Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Boyd's Key West Campground
- Seven Mile Bridge
- Sunset Park
- Curry Hammock State Park




