Skip to main content

Check out our selection of great vacation rentals in Florida Keys

Filter by:


Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Southernmost Point Guest House & Garden Bar

Duval, Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach. Features include a free hot American breakfast and a hot tub.The property is located across 4 buildings. The location was great. We had very nice room furnished with attention to detail. The breakfast was great too.

Show more Show less
9.2
Wonderful
1,147 reviews
Price from
$343.85
per night

The Speakeasy Inn and Rum Bar

Duval, Key West

The Speakeasy Inn and Rum Bar features accommodation within 400 metres of the centre of Key West, with free WiFi, and a kitchenette with a microwave, a fridge and kitchenware. This bed and breakfast provides free private parking and luggage storage space. Guests can access the bed and breakfast via private entrance. The location was excellent. The room fit my needs. I like it quiet. Loved the rum bar. Lots of happy people there. I would stay there again.

Show more Show less
9.1
Wonderful
157 reviews
Price from
$279
per night

Key West Harbor Inn - Adults Only

Downtown Key West, Key West

Situated in the centre of Key West, 600 metres from Simonton Street Beach, the historic Key West Harbor Inn - Adults Only features accommodation with free WiFi and an indoor pool. The property features pool and garden views, and is 1.8 km from South Beach. The bed and breakfast has facilities for disabled guests. Great location and staff! Given it’s a historic place redesigned to become a hotel, it’s great!

Show more Show less
9.3
Wonderful
428 reviews
Price from
$330
per night

Marreros Guest Mansion - Adult Only

Duval, Key West

Offering a year-round outdoor pool and terrace, this adult-only (21 years +) Marreros Guest Mansion is set in the Duval district in Key West. Duval Street is a 1 minute walk from the property.

Each room at this bed and breakfast is air conditioned and comes with a flat-screen TV. Some units have a seating area where you can relax. We had time to spare in Florida before leaving for NYC, we decided to spend 2 nights in Key West and this place was great. Very charming and well decorated.

Show more Show less
9.4
Wonderful
139 reviews
Price from
$279
per night

Key West Bed and Breakfast

Downtown Key West, Key West

Featuring garden views and a garden, Key West Bed and Breakfast features accommodation attractively located in Key West, within a short distance of Fort Zachary Taylor State Park Beach, Duval Street and Mallory Square. The air-conditioned accommodation is 1.7 km from South Beach. The property is 700 metres from the city centre and 1.1 km from Simonton Street Beach. Lovely and beautiful house with cute furnitures. They have lovely garden and poor, very good and quiet location. Staffs are very friendly.

Show more Show less
9.3
Wonderful
234 reviews
Price from
$290
per night

Old Town Manor

Duval, Key West

This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1.6 km from the Southernmost Point. Guests will enjoy a daily breakfast including pastries, organic fruit, and dessert cakes during their stay. We had a great stay at Old Town Manor - friendly staff, delicious breakfast, large room. Will definitely stay here again once we will be back in Key West.

Show more Show less
9
Wonderful
950 reviews
Price from
$204
per night

Coconut Bay Resort - Key Largo

Key Largo

Guests at this Key Largo resort can venture into the Gulf of Mexico on a kayak or paddle boat, swim in the heated outdoor pool, or stay in and read emails through free Wi-Fi.

All guest rooms include a flat-screen cable TV, microwave, and small refrigerator. Select rooms at this Key Largo Coconut Bay Resort include a patio, water view, and dining area. Coffee-making facilities are provided. The property, the location and the hospitality were all perfect. We had great time with the family. We were watching the sunset from our cottage every evening. I highly recommend to stay here.

Show more Show less
9.2
Wonderful
110 reviews
Price from
$255
per night

Key West Villas

Duval, Key West

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area.

Key West Villas guests can hire a bicycle and explore Key West. A guest launderette is available as well. The couple who run the villas are charming. They greeted us with cocktails and made us feel comfortable at all times. The place is beautiful and the location is fantastic, just off the main street in Key West.

Show more Show less
9.7
Exceptional
340 reviews
Price from
$299
per night

The Artist House

Duval, Key West

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street. The Artist House guests will enjoy a daily continental breakfast and spa hot tub. The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.

Show more Show less
9.1
Wonderful
140 reviews
Price from
$386.25
per night

Andrews Inn & Garden Cottages

Duval, Key West

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

A flat-screen TV and an iPod docking station are featured in each classic room at this Key West bed and breakfast. Guests will also enjoy the convenience of a refrigerator in their room. Rooms also have a clock radio with auxiliary cables. The inn is beautiful, perfectly located, excellent amenities and benefits (breakfast, happy hours, pool), the room was cute and nothing was missing, and Isabella is the nicest person you could meet in Key West. Thank you!

Show more Show less
9.4
Wonderful
105 reviews
Price from
$306.27
per night

Most booked vacation rentals in Florida Keys this month

FAQs about vacation rentals in Florida Keys

Vacation Rentals that guests love in Florida Keys