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Guest favorite
Courtney'S Place Historic Cottages & Inns
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Outdoor swimming pool
Situated merely 1.3 km from Bayview Park, the 2-star Courtney'S Place Historic Cottages & Inns Key West features Wi-Fi in public areas and street parking on site. The guest house is a good starting point for exploring Key West, including Key West Butterfly and Nature Conservatory, which is only 9 minutes' walk away.
There is an outdoor swimming pool to relax after a busy day.
Courtney'S Place Historic Cottages & Inns
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Outdoor swimming pool
Courtney'S Place Historic Cottages & Inns
Situated merely 1.3 km from Bayview Park, the 2-star Courtney'S Place Historic Cottages & Inns Key West features Wi-Fi in public areas and street parking on site. The guest house is a good starting point for exploring Key West, including Key West Butterfly and Nature Conservatory, which is only 9 minutes' walk away.
There is an outdoor swimming pool to relax after a busy day.
Authors Key West Guesthouse
- Picnic area/ Tables
- Housekeeping
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Plunge pool
The comfortable Authors Key West Guesthouse, located within 5 minutes' walk of Bayview Park, offers an outdoor swimming pool, Wi-Fi in the rooms. This 4-star guest house is a good starting point for exploring Key West, including Fleming Street, which is just 350 metres away.
To diversify your leisure time, a sundeck and a picnic area are provided on site.
Authors Key West Guesthouse
- Picnic area/ Tables
- Housekeeping
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Plunge pool
Authors Key West Guesthouse
The comfortable Authors Key West Guesthouse, located within 5 minutes' walk of Bayview Park, offers an outdoor swimming pool, Wi-Fi in the rooms. This 4-star guest house is a good starting point for exploring Key West, including Fleming Street, which is just 350 metres away.
To diversify your leisure time, a sundeck and a picnic area are provided on site.
Caribbean House
- In-room breakfast
-
Car park
US$ 25 per day
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun loungers
The 3-star Caribbean House Hotel Key West, located in the museum district of Key West, nearly a 15-minute walk from the Harry S. Truman Little White House, features views of the city. The hotel offers Wi-Fi in public areas and private car parking on site.
Bicycles for rent are available at this hotel and snorkelling, diving, and bike riding can be organised.
Caribbean House
- In-room breakfast
-
Car park
US$ 25 per day
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun loungers
Caribbean House
The 3-star Caribbean House Hotel Key West, located in the museum district of Key West, nearly a 15-minute walk from the Harry S. Truman Little White House, features views of the city. The hotel offers Wi-Fi in public areas and private car parking on site.
Bicycles for rent are available at this hotel and snorkelling, diving, and bike riding can be organised.
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Best-rated
Key West Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 15 per day
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
Situated 14 minutes' walk from Southernmost Point of the Continental US Monument, Key West Villas offers guests to enjoy a sunbathing terrace, a shared lounge, and a golf course. The 7-room villa features opportunities for snorkelling in the area, not far from Papa's Pilar Rum Distillery.
This accommodation offers bicycles for rent and features an outdoor swimming pool. Treat yourself to the spa's amenities, which include a Jacuzzi.
Key West Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 15 per day
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
Key West Villas
Situated 14 minutes' walk from Southernmost Point of the Continental US Monument, Key West Villas offers guests to enjoy a sunbathing terrace, a shared lounge, and a golf course. The 7-room villa features opportunities for snorkelling in the area, not far from Papa's Pilar Rum Distillery.
This accommodation offers bicycles for rent and features an outdoor swimming pool. Treat yourself to the spa's amenities, which include a Jacuzzi.
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Great deal
Old Town Suites
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
The 3-star Old Town Suites Key West hotel offers easy access to The Ernest Hemingway Home and Museum, which is situated approximately a 5-minute walk away. Experience spacious rooms and dry cleaning and a self-serve laundry at the guest house.
Old Town Suites
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Old Town Suites
The 3-star Old Town Suites Key West hotel offers easy access to The Ernest Hemingway Home and Museum, which is situated approximately a 5-minute walk away. Experience spacious rooms and dry cleaning and a self-serve laundry at the guest house.
The Garden House - Adult Only
- In-room breakfast
-
Car park
US$ 30 per day
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Comprising 3 rooms, the 2-star The Garden House - Adult Only Hotel Key West is near a shopping district, 25 minutes' stroll from Higgs Beach Dog Park. Situated fairly close to US 1 Mile Marker 0 in a historical neighbourhood, the guest house features a swimming pool.
The Garden House - Adult Only
- In-room breakfast
-
Car park
US$ 30 per day
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
The Garden House - Adult Only
Comprising 3 rooms, the 2-star The Garden House - Adult Only Hotel Key West is near a shopping district, 25 minutes' stroll from Higgs Beach Dog Park. Situated fairly close to US 1 Mile Marker 0 in a historical neighbourhood, the guest house features a swimming pool.
Westwinds Inn
- BBQ facilities
- Housekeeping
- Air conditioning
- Flat-screen TV
- Laundry
- Heated swimming pool
Located within 5 minutes' walk of the vintage parish "Saint Paul's Episcopal Church of Key West", the 4-star non-smoking Westwinds Inn Key West offers a picnic area and a library. Boasting a tropical location 2.6 km from a historical place like the historic fort "West Martello Tower", this Key West hotel includes 2 outdoor swimming pools.
Beach facilities at Westwinds Inn include beach towels.
Westwinds Inn
- BBQ facilities
- Housekeeping
- Air conditioning
- Flat-screen TV
- Laundry
- Heated swimming pool
Westwinds Inn
Located within 5 minutes' walk of the vintage parish "Saint Paul's Episcopal Church of Key West", the 4-star non-smoking Westwinds Inn Key West offers a picnic area and a library. Boasting a tropical location 2.6 km from a historical place like the historic fort "West Martello Tower", this Key West hotel includes 2 outdoor swimming pools.
Beach facilities at Westwinds Inn include beach towels.
New Orleans House - Gay Male Adult Guesthouse
- Cookware/ Kitchen utensils
-
Car park
US$ 10 per day
- Housekeeping
- Air conditioning
- Live entertainment
- Heated swimming pool
Offering a nightclub and a sun deck, New Orleans House - Gay Male Adult Guesthouse Key West lies in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic decor, a 6-minute walk from South Beach. American cuisine plus a heated pool are provided in this guest house, located just moments from The Ernest Hemingway Home and Museum.
You will find a hot tub in the pool area. This hotel has a fitness centre.
New Orleans House - Gay Male Adult Guesthouse
- Cookware/ Kitchen utensils
-
Car park
US$ 10 per day
- Housekeeping
- Air conditioning
- Live entertainment
- Heated swimming pool
New Orleans House - Gay Male Adult Guesthouse
Offering a nightclub and a sun deck, New Orleans House - Gay Male Adult Guesthouse Key West lies in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic decor, a 6-minute walk from South Beach. American cuisine plus a heated pool are provided in this guest house, located just moments from The Ernest Hemingway Home and Museum.
You will find a hot tub in the pool area. This hotel has a fitness centre.
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Top location
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Private beach
Nautilus...Ocean Front Cottage Retreat ~
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Tennis court
- Pool with view
Featuring a heated pool, Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is located in a beach part of Cudjoe Key, a 19-minute walk from Gopher Key. Providing guests with Wi-Fi and a car park, the 2-bedroom villa is 4.6 km from Knockemdown Key.
Staying at this Cudjoe Key property, guests can enjoy snorkelling, canyoning, and fisheries, or relax in a Jacuzzi.
Nautilus...Ocean Front Cottage Retreat ~
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Tennis court
- Pool with view
Nautilus...Ocean Front Cottage Retreat ~
Featuring a heated pool, Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is located in a beach part of Cudjoe Key, a 19-minute walk from Gopher Key. Providing guests with Wi-Fi and a car park, the 2-bedroom villa is 4.6 km from Knockemdown Key.
Staying at this Cudjoe Key property, guests can enjoy snorkelling, canyoning, and fisheries, or relax in a Jacuzzi.
Rose Lane Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 25 per day
- Concierge desk
- Air conditioning
- Flat-screen TV
- Heated swimming pool
Situated only 0.6 km from the downtown commercial zoned Duval Street, the 6-room Rose Lane Villas Key West entices guests with windsurfing, snorkelling, and diving in the area. Providing guests with Wi-Fi and private parking, this accommodation is within a few blocks of the 19 - acre Key West Cemetery.
Rose Lane Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 25 per day
- Concierge desk
- Air conditioning
- Flat-screen TV
- Heated swimming pool
Rose Lane Villas
Situated only 0.6 km from the downtown commercial zoned Duval Street, the 6-room Rose Lane Villas Key West entices guests with windsurfing, snorkelling, and diving in the area. Providing guests with Wi-Fi and private parking, this accommodation is within a few blocks of the 19 - acre Key West Cemetery.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
The 2-bedroom Vacation Rental Florida Keys Marathon villa, located right around the corner from Vaca Cut Bridge, can host up to 6 guests. Located just a 6-minute walk from Coffins Patch, this property provides Wi-Fi and a car park.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Vacation Rental Florida Keys
The 2-bedroom Vacation Rental Florida Keys Marathon villa, located right around the corner from Vaca Cut Bridge, can host up to 6 guests. Located just a 6-minute walk from Coffins Patch, this property provides Wi-Fi and a car park.
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Beach access
Cohiba At Azul Mansion Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
The comfortable Cohiba At Azul Mansion Key West Hotel is nestled about 600 metres from the very unusual Key West Cemetery and features a heated pool. This Key West guest house provides Wi-Fi in the rooms.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
Cohiba At Azul Mansion Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
Cohiba At Azul Mansion Key West
The comfortable Cohiba At Azul Mansion Key West Hotel is nestled about 600 metres from the very unusual Key West Cemetery and features a heated pool. This Key West guest house provides Wi-Fi in the rooms.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
Dk21 Palm Breeze- Villa 5030
- Cookware/ Kitchen utensils
- Air conditioning
- Laundry
- Ironing facilities
- Golf centre
- Patio
Situated nearly 5 minutes' walk from Hawks Cay Boulevard, the 2-bedroom Dk21 Palm Breeze- Villa 5030 Duck Key offers guests to take advantage of playground and a golf course. At this Duck Key villa, located within reach of The Calm Waters Spa, guests can enjoy cycling and fisheries.
Dk21 Palm Breeze- Villa 5030
- Cookware/ Kitchen utensils
- Air conditioning
- Laundry
- Ironing facilities
- Golf centre
- Patio
Dk21 Palm Breeze- Villa 5030
Situated nearly 5 minutes' walk from Hawks Cay Boulevard, the 2-bedroom Dk21 Palm Breeze- Villa 5030 Duck Key offers guests to take advantage of playground and a golf course. At this Duck Key villa, located within reach of The Calm Waters Spa, guests can enjoy cycling and fisheries.
Dk22 Palm Villa - Villa 5115
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
- Laundry
- Golf centre
- Plunge pool
During the stay at Dk22 Palm Villa - Villa 5115 Duck Key, guests can indulge in cycling and fisheries or visit Dolphin Research Center, located a 10-minute drive away. The 2-bedroom villa features a heated pool and is ideal for up to 6 guests.
Dk22 Palm Villa - Villa 5115
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
- Laundry
- Golf centre
- Plunge pool
Dk22 Palm Villa - Villa 5115
During the stay at Dk22 Palm Villa - Villa 5115 Duck Key, guests can indulge in cycling and fisheries or visit Dolphin Research Center, located a 10-minute drive away. The 2-bedroom villa features a heated pool and is ideal for up to 6 guests.
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Beach access
Aria At Azul Mansion Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
The comfortable Aria At Azul Mansion Key West Hotel is nestled within 5 minutes' walk of the historic Saint Mary Star of the Sea Church and features an outdoor swimming pool. This Key West guest house provides Wi-Fi throughout the property.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
Aria At Azul Mansion Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
Aria At Azul Mansion Key West
The comfortable Aria At Azul Mansion Key West Hotel is nestled within 5 minutes' walk of the historic Saint Mary Star of the Sea Church and features an outdoor swimming pool. This Key West guest house provides Wi-Fi throughout the property.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
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Beach access
Honey At Scarlet Mango Inn Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
The comfortable Honey At Scarlet Mango Inn Key West, located nearly a 5-minute walk from the downtown commercial zoned Duval Street and just 1 km from Memorial Sculpture Garden, features an outdoor swimming pool for guests to take a dip in. Wi-Fi is included in the rooms.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
Honey At Scarlet Mango Inn Key West
- Free parking
- Concierge desk
- Flat-screen TV
- Ironing facilities
- Fitness centre
- Heated swimming pool
Honey At Scarlet Mango Inn Key West
The comfortable Honey At Scarlet Mango Inn Key West, located nearly a 5-minute walk from the downtown commercial zoned Duval Street and just 1 km from Memorial Sculpture Garden, features an outdoor swimming pool for guests to take a dip in. Wi-Fi is included in the rooms.
If you like an active lifestyle, windsurfing, snorkelling, and fisheries are available on site.
Villa Del Sol - Waterfront - Amazing Sunset Views!
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Staying at the 2-bedroom Villa Del Sol - Waterfront - Amazing Sunset Views! Duck Key, guests can visit Dolphin Research Center, which is about a 10-minute drive away. Offering parking as well as Wi-Fi, this Duck Key villa is situated in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys.
Villa Del Sol - Waterfront - Amazing Sunset Views!
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Villa Del Sol - Waterfront - Amazing Sunset Views!
Staying at the 2-bedroom Villa Del Sol - Waterfront - Amazing Sunset Views! Duck Key, guests can visit Dolphin Research Center, which is about a 10-minute drive away. Offering parking as well as Wi-Fi, this Duck Key villa is situated in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys.
Are you in a hurry?
Here is a quick list of hotels in Summerland Key, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Courtney'S Place Historic Cottages & Inns |
9.0 / 10 (1028 Reviews) |
From 219$ | |
| Authors Key West Guesthouse |
8.8 / 10 (823 Reviews) |
From 134$ | |
| Alexander Palms Court - No Hidden Resort Fees! |
8.5 / 10 (713 Reviews) |
From 135$ | |
| Caribbean House |
8.9 / 10 (286 Reviews) |
From 142$ | |
| Key West Villas |
9.7 / 10 (267 Reviews) |
From 314$ |
Frequently Asked Questions
What are the best family holiday homes in Summerland Key near the beach?
Alexander Palms Court offers a family-friendly atmosphere just two blocks from South Beach. The hotel has spacious accommodations with private bathrooms, making it suitable for larger family groups.
Visit South Beach for fun water activities like snorkeling; it's less crowded in the morning before 10am.
Which holiday homes in Summerland Key have pools for families?
Alexander Palms Court features a heated lagoon-style pool that's perfect for family relaxation. Another option is Authors Key West Guesthouse, which also provides a year-round outdoor swimming pool.
For a quieter pool experience, consider visiting in the afternoons when most families are out exploring.
Are there any holiday homes in Summerland Key suitable for family gatherings?
Old Town Suites offers ample outdoor space designed for social gatherings and family events. The hotel's combination of self-catering and hotel services provides great flexibility for families.
Book a unit with a fully equipped kitchen in advance to prepare family meals together and save on dining out.
What holiday homes in Summerland Key are near main attractions?
Authors Key West Guesthouse is close to popular sites like Duval Street and the Southernmost Point buoy landmark. This location makes it easy for families to explore local attractions on foot.
Start your day early to beat the crowds at nearby attractions, especially the Southernmost Point, which can get busy after 10am.
Which holiday homes in Summerland Key are pet-friendly for family vacations?
Unfortunately, many options like Caribbean House promote a pet-free environment to ensure a tranquil stay. Families looking for pet-friendly accommodations may need to inquire directly with smaller guesthouses.
Consider booking during the off-season, like September to October, when room choices may be more flexible and accommodating for pets.
Are there holiday homes in Summerland Key with breakfast included?
Authors Key West Guesthouse provides a complimentary breakfast with fresh pastries and fruits, enhancing the family stay experience. This can help families save time and money each morning.
Plan breakfast for around 9am to enjoy a quieter meal, as it tends to get busier closer to 10am.
What budget-friendly holiday homes are there in Summerland Key?
Caribbean House and Old Town Suites offer affordable rates while still providing charming accommodations. These options are perfect for families on a budget looking to enjoy their stay without overspending.
Look for deals during the shoulder seasons, like May or September, when prices can drop and availability is higher.
What local activities should families consider during their stay in Summerland Key?
Families can enjoy snorkeling at nearby beaches, visit the Ernest Hemingway Home, or explore the Key West Butterfly and Nature Conservatory. Each activity caters to different age groups, ensuring fun for everyone.
Plan snorkeling trips for weekdays to avoid larger crowds often seen on weekends, making it a more enjoyable experience.
How can families get around in Summerland Key efficiently?
Biking is a popular way to explore Summerland Key. Many hotels, such as Authors Key West Guesthouse, offer bike rentals to access nearby attractions like Duval Street and local beaches quickly.
Rent bikes in the morning and return them by 4pm to avoid peak rental times and ensure availability.
What seasonal events can families plan to attend in Summerland Key?
Families can join the annual Fantasy Fest held in October, featuring parades, costumes, and family-friendly activities. It's a fun way to experience the local culture together.
Book accommodations early for Fantasy Fest, as hotels fill up quickly due to high demand during this festive time.