Holiday Rentals in Key West
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777 rentals in Key West.
524 Elizabeth St. #2
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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BLACK FRIDAY SPECIAL 20% OFF JUN. thru OCT. 2025 Escape to "Oasis on 18th"
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Upgraded 2-Bedroom Condo-Olympic size Pool- Fitness room-Beach-on Atlantic Ocean
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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**SWEET AMERICANA * OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
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Rare Find! 2 Comfortable Rooms In The Heart Of Key West Minutes From The Beach!
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Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Brand New Build! Larkshine House - Pool
Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps
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Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secret Courtyard cottage steps from Duval
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Welcome to Kokomo Cottage-A311
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serene Retreat w/ Waterfront Balcony & Easy Access to Paddleboarding
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Key West Butterfly Garden Flat - Minutes from Beach & Old Town Perfect for
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Penny' s Perfect Place
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Gypsyginny's Hideaway in downtown Key West
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Touch Of Cuba In Key West
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Cozy 2-bedroom cottage in Old Town Key West, with shared pool
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hyatt Beach House Resort, Key West, Florida - FANTASY FEST WEEK 2023
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Location for Your Staycation! Spacious Deluxe Room w/ Pool View
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.
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Stunning 2BD Oceanfront Escape, Breathtaking Views - pool, hot tub and more
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Prestigious | Gym | Pool | Marina | Concierge
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean Front Presidential Suite | Beachside Resort
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ocean Front Presidential Suite | Beachside Resort
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Leo’s Lodge | Newly Updated!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Direct Ocean View from Your Condo-No Contact Check-In
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MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
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Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
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Charming 1-bedroom/1-bath apartment in historical home with pool in Key West
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
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ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
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MIMOSAS ON PINE ~ 3 Bedroom, 2.5 Bath Home w/ Pool & Spa in The Meadows!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Breezy Key West First-Floor Condo w/ Pool Access
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
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Heron House | Canal Front 3-Bedroom Home w/ Private Boat Docking in Key Haven
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom Suite w/ Outdoor Pool in Old Town Key West
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub
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Waterfront Resort, Private Beach, Boat Docks, Sleeps 6, Pool, Hot Tub, Hyatt
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Key West Beach Cottage: Walk to Beaches!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
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Villa Paradiso: A unique mid-town paradise
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������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 777
Frequently Asked Questions about Key West
- Yes, here are some popular holiday rentals in Key West that have a pool:
- 2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
- 4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- CASA ROYALE- OLD TOWN KEY WEST 4 BEDROOM WITH POOL
- Yes, here are some popular holiday rentals in Key West that have internet access:
- 2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
- 4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- CASA ROYALE- OLD TOWN KEY WEST 4 BEDROOM WITH POOL
- The best pet friendly rentals in Key West are:
- 2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
- 4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- 2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina
- Some of the most popular kid friendly rentals in Key West are:
- 2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
- 4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- CASA ROYALE- OLD TOWN KEY WEST 4 BEDROOM WITH POOL
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