Luxury Vacation Rentals in Key West

(19 rentals)
booking message booking message
Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

$741

avg/night

$741
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...

View all property information

Property Type

Key West House

Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...

See all reviews

Show less

Key West House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

$965

avg/night

$965
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants ...

View all property information

Property Type

Key West House

Featured review

"Wonderful property wonderful hosts!"

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...

See all reviews

Show less

Key West House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

$724

avg/night

$724
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...

View all property information

Property Type

Key West House

Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...

See all reviews

Show less

Key West Yacht
5 BR | 5.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5.5 bathrooms
3 reviews

$1180

avg/night

$1,180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

VACATION RENTALSFlorida offers amazing opportunities on the water aboard private yacht, Lady Grace, which is available for winter vacation rentals in Key West. Lady Grace provides a relaxing retreat and the thrill of living on your own private 92-foot yacht with plenty of space for enjoying time ...

View all property information

Property Type

Key West Yacht

Featured review

"Amazing Week Cruising"

“My family and I just spent an amazing week cruising around the Gulf Of Mexico visiting Key West and the Dry Tortugas onboard The Lady Grace. The accommodations were incredible with spacious staterooms ...

See all reviews

Show less

Key West Villa
6 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1778

avg/night

$1,778
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

View all property information

Property Type

Key West Villa

Featured review

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...

See all reviews

Show less

Key West House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to beach: 50 yards to One block from fantastic beach

$1037

avg/night

$1,037
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This one of a kind beautiful home was built in 1912 by one of the first cigar makers. It is listed on the National registry of historic homes and has been showcased in the Holiday Parade of Homes. The home was restored and expanded in 2002 Key West contractor Richard Manley with the highest level of ...

View all property information

Property Type

Key West House

Show less

Key West House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

$1122

avg/night

$1,122
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa ...

View all property information

Property Type

Key West House

Show less

Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$1066

avg/night

$1,066
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Suncatcher on the ocean is new to the rental pool at 1800 Atlantic. A fabulous property with many upgrades throughout. Totally renovated from top to bottom with high end finishes and no attention to detail spared. We are excited to offer it for rent for the first time. Tastefully decorated in Island ...

View all property information

Property Type

Key West Condo

Show less

Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$988

avg/night

$988
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Tom's Oceanfront Penthouse is a spectacular oceanfront unit features 3 bedrooms and 2 bathrooms in a prime location within the complex. It is conveniently situated near the elevator and offers secure covered parking in the garage for vehicles under 6 feet 4 inches in height.Spanning approximately ...

View all property information

Property Type

Key West Condo

Show less

Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$1840

avg/night

$1,840
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key WestThis charming Conch house features a queen bed in the master bedroom, a queen bed in the first guest bedroom, and two queen beds in the second guest bedroom. The kitchen has been beautifully renovated, and there is a wonderful ...

View all property information

Property Type

Key West House

Show less

Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$1795

avg/night

$1,795
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV ...

View all property information

Property Type

Key West Condo

Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

See all reviews

Show less

Key West Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$915

avg/night

$915
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

3 Bedroom, 3 Bath Partial Ocean ViewAtlantic Sunrise is the only 3-bedroom, 3-bath unit in the complex, spanning approximately 2,000 square feet and accommodating up to 8 guests. It features two master suites, each with a king bed, while the third bedroom has 2 twin beds. Additionally, there is a ...

View all property information

Property Type

Key West Condo

Show less

Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

$1850

avg/night

$1,850
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever ...

View all property information

Property Type

Key West Condo

Featured review

"Great vacation rental!"

We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only ...

See all reviews

Show less

Key West Condo
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$792

avg/night

$792
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half bathrooms, located at 1800 Atlantic. Enjoy the balmy breezes from your 60-foot private wrap-around balcony, which offers a stunning view of the Atlantic Ocean.The condominium includes renovated kitchens and ...

View all property information

Property Type

Key West Condo

Show less

Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$870

avg/night

$870
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Blue Haven: An Exquisite Oceanfront Penthouse – Complete Remodel with Direct Ocean Views and Massage Chair – Premier Unit on Property Blue Haven is the premiere property in this complex. This luxury penthouse condominium is unbelievable. You will not want to leave. Nestled on the shore of ...

View all property information

Property Type

Key West Condo

Show less

Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...

View all property information

Property Type

Key West House

Featured review

"Highly Recommend!"

My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...

See all reviews

Show less

Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$1364

avg/night

$1,364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts ...

View all property information

Property Type

Key West Condo

Show less

Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

$1000

avg/night

$1,000
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Keys to Paradise: A 5-Star Beachside RetreatThis beautiful 3-bedroom, 2-bath condo is located in a private beachside resort, conveniently close to Old Town Key West and just steps away from the beach. It's also an easy bike ride to all that Key West has to offer.Keys to Paradise is a direct ...

View all property information

Property Type

Key West Condo

Featured review

"Absolutely Amazing"

The condo was beautiful, offering stunning views of the harbor and boat races. It was conveniently located near Duval Street but far enough awayeace and quiet. Alice and Charli to enjoy some pe were fantastic ...

See all reviews

Show less

Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$787

avg/night

$787
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms ...

View all property information

Property Type

Key West Condo

Featured review

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO ...

See all reviews

Show less

Map
Expand map Close map
Key West Vacation Rentals