Key West · Old Town · Waterfront stays
Best Hotels
in Key West
Five stays. Five different trips. Compare beach access, pools, location and room space—then check the stay that fits your dates.
Compare the five hotels ↓
What matters most for your stay?
Private beachPier House →Waterfront viewsOcean Key →
Garden hideawayThe Gardens →
Pools + friendsWinslow’s →
More suite spaceSanta Maria Suites →Affiliate disclosure: We may earn a commission if you book through our links, at no extra cost to you. These are researched recommendations, not firsthand stay reviews.
Five Key West hotels, side by side.
Waterfront does not always mean beach access. Compare the setting and room setup before choosing your stay.
| Hotel | Best for | Area | Beach setup | Parking | Booking |
|---|---|---|---|---|---|
| Pier House Resort & SpaPhotos + details ↓ | First trips + beach time | Gulf end of Duval | Private on-site beach | Self-parking · $40/night + tax | See prices ↗ |
| Ocean Key Resort & SpaPhotos + details ↓ | Couples + sunset plans | Gulf end of Duval | Waterfront; no on-site beach | Valet only · nightly fee | See prices ↗ |
| The Gardens HotelPhotos + details ↓ | Couples + guests ages 16+ | Angela Street / Old Town | Off-site beach outing | Paid self-parking | See prices ↗ |
| Winslow’s BungalowsPhotos + details ↓ | Friends + pool breaks | Truman Avenue / Old Town | Off-site beach outing | Limited on-site · $30/night | See prices ↗ |
| Santa Maria Suites ResortPhotos + details ↓ | Families + shared stays | Simonton / south Old Town | Nearby Southernmost Beach services | On-site · $40/night + tax | See prices ↗ |
Private on-site beach
Photos + booking details ↓See prices ↗
Waterfront; no on-site beach
Photos + booking details ↓See prices ↗
Published parking details checked October 4, 2026. Rates and fees can change. Enter dates and guests on Expedia to compare the full stay total, mandatory charges and cancellation terms.
Resort waterfront setting · 7 photos · Tap image to enlarge
For beach time + Old Town exploring
Pier House Resort & Spa
A beach afternoon without giving up the central location.
At 1 Duval Street, Pier House puts a private beach, pool and spa beside Old Town plans. Start here if you want restaurants and sunset outings close by, with somewhere to swim and unwind at the hotel.
- Best for
- First trips + beach time
- Area
- Gulf end of Duval
- Beach access
- Private on-site beach
- Pool
- Outdoor pool + whirlpool
- Walkability
- Duval Street + Mallory Square nearby
- Parking
- Self-parking · $40/night + tax
More booking details
What paying more gets you: An oceanfront room or suite buys a more specific view or extra space. The beach and central location are the reasons to consider the resort itself; choose the room category that delivers the view you want.
Who should skip it: You want a secluded inn, a long stretch of beach, or the lowest possible total after hotel extras.
Pick the right room: Garden, partial-water and oceanfront categories are different purchases. Compare the exact view, bed setup and accessible features on the selected listing.
Fees + total cost: Self-parking is $40 plus tax per night. A daily resort fee also applies. Compare the mandatory charges in your selected rate’s full stay total, including taxes and any amounts payable at the property.
Worth knowing: This is a private beach at an Old Town resort. Choose it for a convenient beach-and-city combination rather than expecting a sprawling beach destination.
Information checked October 4, 2026. Hotel FAQs ↗ · Hotel fact sheet ↗
Opens Expedia · Enter dates and guests to see available rooms and the full price.
Waterfront pool and loungers · 6 photos · Tap image to enlarge
For waterfront days + dinner plans
Ocean Key Resort & Spa
Make the water view part of the vacation.
Ocean Key fits a trip built around a waterfront pool, a balcony and Old Town evenings. Its position beside Mallory Square keeps sunset plans close, but this is a seawall setting: there is no beach at the hotel.
- Best for
- Couples + sunset plans
- Area
- Gulf end of Duval
- Beach access
- Waterfront; no on-site beach
- Pool
- Waterfront pool + LIQUID Lounge
- Walkability
- Duval Street + Mallory Square nearby
- Parking
- Valet only · nightly fee
More booking details
What paying more gets you: A named oceanfront category or larger suite buys a different view and layout. If the balcony is your priority, compare partial-view, harbor-view and oceanfront descriptions before paying for the upgrade.
Who should skip it: Walking directly from the hotel onto sand is essential, or you want your evenings away from the Duval and Mallory Square area.
Pick the right room: Book the view explicitly. A waterfront hotel address does not mean every room has an uninterrupted water view. Check the listed beds and sofa-bed arrangements for your party.
Fees + total cost: The hotel lists a $69 daily resort fee. Valet-only parking carries a separate nightly charge, and the garage clearance is 6 ft 4 in. Review taxes, parking and mandatory charges in the selected rate before booking.
Worth knowing: Beach towels are provided for off-site use. Beach visits require a separate outing; there is no on-site sandy beach.
Information checked October 4, 2026. Hotel FAQs ↗ · Hotel amenities ↗
Opens Expedia · Enter dates and guests to see available rooms and the full price.
Pool surrounded by tropical gardens · 7 photos · Tap image to enlarge
For a boutique stay in Old Town
The Gardens Hotel
Step out for dinner. Come back to the garden.
Choose The Gardens for shaded grounds, distinctive rooms and a smaller boutique setting in Old Town. It suits travelers who want a retreat between outings, with the Wine Gallery adding a reason to spend an evening on property.
- Best for
- Couples + guests ages 16+
- Area
- Angela Street / Old Town
- Beach access
- Off-site beach outing
- Pool
- Outdoor pools in a garden setting
- Walkability
- Central Old Town, near Duval
- Parking
- Paid self-parking
More booking details
What paying more gets you: Compare the room, suite and cottage layouts for extra living space or a different garden setting. Choose the accommodation itself carefully; the cottages and main guest rooms have different features.
Who should skip it: You are traveling with children under 16, need direct beach access, or want a large resort with extensive family facilities.
Pick the right room: The hotel welcomes guests ages 16 and older. Review the selected room’s access, steps, bed configuration and any private outdoor space; do not assume all cottages or rooms share the same setup.
Fees + total cost: Self-parking is charged separately. Compare parking, breakfast inclusions, any mandatory property charges and the cancellation deadline in the selected Expedia rate. A small hotel is not automatically a fee-free stay.
Worth knowing: The Wine Gallery features a self-serve tasting system; wine and other purchases should be budgeted separately unless explicitly included in your package.
Information checked October 4, 2026. Hotel information ↗ · Property amenities ↗ · Expedia property details ↗
Opens Expedia · Enter dates and guests to see available rooms and the full price.
Pool and loungers beside the bungalows · 18 photos · Tap image to enlarge
For pool time between Old Town plans
Winslow’s Bungalows
Give the group somewhere to gather between outings.
Winslow’s brings historic buildings, tropical grounds and three pools to an Old Town stay. Choose it when shared pool time and an easy base for exploring matter more than being on the waterfront.
- Best for
- Friends + pool breaks
- Area
- Truman Avenue / Old Town
- Beach access
- Off-site beach outing
- Pool
- Three swimming pools + Bungalow Bar
- Walkability
- Old Town dining + sightseeing
- Parking
- Limited on-site · $30/night
More booking details
What paying more gets you: A patio, deck or suite can give you more room to spread out. Compare the exact category: a bungalow name does not guarantee a large room, separate living space or a kitchen.
Who should skip it: You need guaranteed parking, a sandy beach at the hotel, or one large suite where the whole group can stay together.
Pick the right room: Check occupancy and bed count before booking multiple rooms. Annex rooms, bungalows and suites have different layouts and locations; adjoining rooms should never be assumed.
Fees + total cost: Limited on-site parking is listed at $30 per night, with requests made at check-in. Compare any mandatory property charges, breakfast inclusion and taxes in the selected rate’s full total.
Worth knowing: Bungalow Bar and the pools make this an editorial pick for friends who want to gather at the hotel. Pool access and room occupancy follow hotel rules, even when booking several rooms.
Information checked October 4, 2026. Hotel rooms + amenities ↗ · Hotel FAQs ↗
Opens Expedia · Enter dates and guests to see available rooms and the full price.
Courtyard pool and suite buildings · 13 photos · Tap image to enlarge
For space, a kitchen + pool time
Santa Maria Suites Resort
Share the trip without sharing one small room.
Santa Maria makes the room layout a bigger part of the decision. Its two-bedroom suite options offer living space, a kitchen and laundry, while two courtyard pools and nearby beach services add places to spend the day.
- Best for
- Families + shared stays
- Area
- Simonton / south Old Town
- Beach access
- Nearby Southernmost Beach services
- Pool
- Two heated courtyard pools
- Walkability
- South Duval + Southernmost area
- Parking
- On-site · $40/night + tax
More booking details
What paying more gets you: Separate bedrooms, a living room, kitchen and washer/dryer can make a shared stay easier. Compare the full suite total against the cost of multiple rooms, including extra-person charges.
Who should skip it: You want a hotel directly on the sand, prefer the Gulf end of Duval, or need step-free access without arranging a suitable suite.
Pick the right room: Flat and bi-level suites have different layouts and stairs. There is no elevator. The hotel lists a maximum of five guests per suite and a primary reservation guest age of 25 or older; enter everyone’s ages when comparing rates.
Fees + total cost: The published daily resort fee is $60 plus tax and includes Southernmost Beach services. Parking is $40 plus tax per night, with one permit per reservation. Extra-person fees apply above two adults; the hotel counts ages 13+ as adults for these charges.
Worth knowing: Southernmost Beach is about two blocks away. Resort-fee beach services include chairs, towels and umbrellas; check the selected rate and operating arrangements before planning your beach day.
Information checked October 4, 2026. Hotel FAQs + policies ↗ · Suite layouts ↗
Opens Expedia · Enter dates and guests to see available rooms and the full price.
Where should you stay in Key West?
Choose the part of Old Town that matches the plans you want close by.
Gulf end of Duval
For Mallory Square, waterfront views and central evenings. Pier House adds a private beach; Ocean Key is a seawall waterfront stay.
Pier House →Ocean Key →
Central Old Town
For exploring on foot with garden or pool breaks in between. Choose boutique surroundings or multiple pools.
The Gardens →Winslow’s Bungalows →
South Old Town
For the Southernmost area, South Duval plans and more space in your suite. Beach access is nearby rather than on property.
Santa Maria Suites →Before you book.
The details that can change which stay is right for you.
Which of these Key West hotels has a private beach?
Pier House has a private on-site beach. Ocean Key is waterfront without an on-site beach. Santa Maria includes services at nearby Southernmost Beach; The Gardens and Winslow’s require a separate beach outing.
Pier House or Ocean Key?
Start with Pier House if direct beach access matters. Consider Ocean Key if the waterfront pool, a chosen balcony view and Old Town sunset plans are your priorities. Compare the full total and exact room category for your dates.
Which hotel fits a family or shared stay?
Santa Maria’s two-bedroom suite options are worth comparing when separate bedrooms and a kitchen matter. Pier House has family room options, and Winslow’s offers different bed configurations. The Gardens welcomes guests ages 16 and older. Enter the full party and ages before comparing rates.
Do you need a car for an Old Town stay?
These five hotels are in Old Town, where many restaurants and attractions can be reached on foot. Airport transfers, heat, mobility needs and trips farther afield still affect your transport plans. If bringing a car, budget for parking and check availability.
What should you compare before booking?
Check the full stay total, mandatory charges, parking, guest occupancy, room view, stairs and cancellation deadline. Property photos may show upgraded accommodation. Book a category that explicitly includes the features you want.
Keep your Key West shortlist handy.
Browse these five picks together in my Expedia collection—or explore more stays for your dates and budget.
Build the rest of your Key West trip.
Found your stay? Plan the days around it.