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House vacation rentals in Key West

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Top-rated house rentals in Key West

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Home in Key Largo

4.84 out of 5 average rating, 426 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, totally renovated home with large TV’s, spacious living area, 2 Large Balconies including roof top great for star gazing, all the amenities of home. Free use of kayaks at the house, Kayak John pennekamp state park steps away from front door. 27 foot boat available 4 all water activities Which I captain.Quiet private street close to all keys activities and restaurants. There is a downstairs space that on a very rare occasion is occupied by myself or family member

Home in Key Largo

4.95 out of 5 average rating, 111 reviews

Mariners Club Resort, Best in the Upper Keys

SPACIOUS AND STUNNING Family Friendly 4+ br home. One of the few to allow 10 guests! POOLS w/ hot tubs MARINA for direct access to reef; diving, snorkeling, fishing & sandbars KAYAKING Pennekemp DISCOUNT to swim with dolphins at DPMMR ACTIVITIES; tennis & pickleball courts, gym & game room. LOCATION: restaurants, bars, grocery and other conveniences PARKING for two cars on site WE ARE LOCALS who know the importance of family time so look no further than this special slice of paradise!

Home in Key West

4.91 out of 5 average rating, 265 reviews

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

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 56” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

Home in Key Largo

4.88 out of 5 average rating, 187 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Summer is here! Escape to a tropical paradise with a stay at the areas HIGHEST REVIEWED fully furnished Camper at Calusa Campground Resort and Marina! Immerse yourself in the ultimate experience with easy access to activities like snorkeling excursions, diving expeditions, kayaking, jet skiing and more. If you're a boat enthusiast, you'll love the convenience of our private boat ramp! Enjoy all the amenities of our space and the wonderfully maintained gated campgrounds. Check out our reviews!

Home in Key Colony Beach

4.91 out of 5 average rating, 127 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

The Snapper House is a spacious 3/2.5 bed/bath duplex with 45' of canal dock frontage, also Includes the Cabana Club with large pool (food/drinks for purchase) and ocean facing beach. Awning extends to dock from sliding doors. TV package includes 100+ channels Each bedroom and living room has a full size flat screen TV. For best WIFI reception, an extender is available and should be used when in the back bedrooms, it's name is the same as the main house with an "ext" at the end (same pw).

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Home in Key Largo

4.89 out of 5 average rating, 104 reviews

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

NO HIDDEN FESS! CASA PALMA IS A LICENSED AND LEGAL VACATION RENTAL WITH HUNDREDS OF 5 STAR REVIEWS AND SUPER HOST STATUS ON ALL VACATION RENTAL SITES. VOTED #1 KEY LARGO VACATION RENTAL! LOCATED IN THE HEART OF KEY LARGO! IT'S THE PERFECT HOME BASE TO EXPLORE THE KEYS! 2 POOLS, BEACH, FREE GOLF CART, FAST WIFI, KAYAKS, TENNIS/PICKELBALL, MARINA WITH BOAT RAMP AND TRAILER PARKING! SLIP RENTAL AVAILABLE! SWIMMING LAGOON! 2 KING BEDS! PLAYGROUND! FREE PARKING! PACK AND PLAY AND BOOSTER SEAT!

Home in Key Largo

4.97 out of 5 average rating, 101 reviews

Little Cottage on an island

Very nice quiet neighborhood. Clean updated home with new appliances. Owner does live on property. There is a shared washer/dryer outside. The house is fully furnished with a queen bed and pullout sofa bed twin size. The home has a beautiful little office to work in and a full kitchen with all dishes and cooking utensils. Centrally located in Key Largo... 1 mile away from everything you need! There is a 21 yrs and over policy - house does have liquor bar. Thank you! 🏝️😊

Home in Marathon

4.92 out of 5 average rating, 125 reviews

Marathon Star - home with hot tub

Completely renovated 3 bedroom house in Marathon. Conveniently located near the Florida Keys Aquarium Encounters and the Marathon Lady. Enjoy a private hot tub and outdoor grill after a long day of Florida sunshine! Our home is not on the water but there is plenty of parking space for your boat trailer if needed. We hope our wonderful space becomes a great home away from home. ***Please see below for more information regarding hurricane season cancellation policy.

Home in Marathon

4.99 out of 5 average rating, 119 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Home in Cudjoe Key

4.82 out of 5 average rating, 243 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Home in Cudjoe Key

4.89 out of 5 average rating, 213 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Key West house rentals

Free parking on premises

Air conditioning

Weekly house rentals

Home in Marathon

4.9 out of 5 average rating, 145 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Home in Cudjoe Key

4.97 out of 5 average rating, 138 reviews

Cudjoe Key Home with a View

Home in Marathon

4.95 out of 5 average rating, 123 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Home in Key West

4.85 out of 5 average rating, 145 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Home in Marathon

4.84 out of 5 average rating, 56 reviews

7 Mile Ocean Bliss

Home in Marathon

4.92 out of 5 average rating, 60 reviews

Blue Ocean Bungalow Canalfront -Fall discounts

Home in Key West

4.9 out of 5 average rating, 108 reviews

Fleming-O

House rentals with a pool

Home in Marathon

4.97 out of 5 average rating, 39 reviews

Oceanfront with Pool near Sombrero Beach

Home in Key Largo

4.96 out of 5 average rating, 50 reviews

Casa Solaris | Key Largo home with Private Pool!

Home in Key Colony Beach

5 out of 5 average rating, 75 reviews

“La casa azul” step 3’ to a private pool

Home in Marathon

4.98 out of 5 average rating, 131 reviews

Marathon one-level home on the Marina - with slip!

Home in Key Colony Beach

4.97 out of 5 average rating, 35 reviews

P23 - New 3 bedroom 2 bath duplex with private po

Home in Marathon

4.98 out of 5 average rating, 97 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Home in Duck Key

4.89 out of 5 average rating, 161 reviews

4 Bed Sanctuary Villa w/ 35 ft Dock & Private Pool

Home in Duck Key

5 out of 5 average rating, 42 reviews

Private Pool Tropical Oasis - Centrally Located

Private house rentals

Home in Key West

4.91 out of 5 average rating, 44 reviews

Key West Paradise

Home in Key Largo

4.9 out of 5 average rating, 372 reviews

Your Keys Getaway!

Home in Marathon

4.98 out of 5 average rating, 82 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

Home in Marathon

5 out of 5 average rating, 35 reviews

Yellowtail Getaway with Boat Dock and Pool 2

Home in Key Colony Beach

4.94 out of 5 average rating, 99 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Home in Key Colony Beach

4.94 out of 5 average rating, 48 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

Home in Key Colony Beach

4.97 out of 5 average rating, 35 reviews

Casa Lago Mar 3/2 with Cabana Club Access

Home in Key Largo

4.81 out of 5 average rating, 83 reviews

Paradise Found-Key Largo Kampground Divers Welcome

Quick stats about house rentals in Key West

Total rentals
560 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
8.4K reviews
Family-friendly rentals
450 properties are a good fit for families
Pet-friendly rentals
250 properties allow pets
Rentals with a pool
380 properties have a pool

Destinations to explore