We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Key West

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
207 rentals in Key West.
Sort by:
Tripadvisor Sort
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West

HISTORIC KEY WEST - Conch House - Sleeps 5

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West

Casa Del Sol, a Key West Vacation (Truman Annex)

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Truman Annex: The Plantation SELF CATERING  beautifully landscaped rear patio, holiday rental in Key West

Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Private Pool with Atlantic Ocean View- 20 minutes away from Key West, holiday rental in Key West

Private Pool with Atlantic Ocean View- 20 minutes away from Key West

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Suites Hotel unit 201, holiday rental in Key West

Key West Suites Hotel unit 201

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Buena Vista Historic Truman Annex, Walk to Duval, Shared Pool, Family Fun!, holiday rental in Key West

Buena Vista Historic Truman Annex, Walk to Duval, Shared Pool, Family Fun!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo, holiday rental in Key West

Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Key West rentals sent straight to your email!
Sunrise At Seaside Condo 2 bedroom 2 bath, holiday rental in Key West

Sunrise At Seaside Condo 2 bedroom 2 bath

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West

Sunrise at Seaside Condo 2 Bedroom

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Real World MTV House Key West, holiday rental in Key West

Real World MTV House Key West

10 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Artist Cottage in Truman Annex, holiday rental in Key West

Artist Cottage in Truman Annex

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Ocean Vista, holiday rental in Key West

Ocean Vista

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A Castle on An Island  Your Santuary Retreat   Key West   Sleeps up to 20, holiday rental in Key West

A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20

8 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -, holiday rental in Key West

Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi, holiday rental in Key West

Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access, holiday rental in Key West

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!, holiday rental in Key West

Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Tom's Chicken Coop:  Nice Ocean View, Pool, Renovated, Close to Beach, holiday rental in Key West

Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Secret Villa I * Old Town with Private Pool, close to Duval!, holiday rental in Key West

Secret Villa I * Old Town with Private Pool, close to Duval!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool, holiday rental in Key West

'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Conch Get Enough!  - Key West's Old Town Truman Annex, holiday rental in Key West

Conch Get Enough! - Key West's Old Town Truman Annex

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Seaside Place Key West FL 5 Bedroom House 4 Baths, holiday rental in Key West

Seaside Place Key West FL 5 Bedroom House 4 Baths

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Attitude Key West (2 Bikes and Wireless Internet), holiday rental in Key West

Attitude Key West (2 Bikes and Wireless Internet)

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Harbor Walk Hideaways, holiday rental in Key West

Harbor Walk Hideaways

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Mermaids House, Historic Old Town Key West, holiday rental in Key West

The Mermaids House, Historic Old Town Key West

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!, holiday rental in Key West

'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Harbour Place 115 in Truman Annex Key West, holiday rental in Key West

Harbour Place 115 in Truman Annex Key West

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval, holiday rental in Key West

'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool, holiday rental in Key West

Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!, holiday rental in Key West

'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Majestic Escape near Duval!  Pool, wifi, renovated 2/2 1/2, private courtyard., holiday rental in Key West

Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!, holiday rental in Key West

'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West

Henry's Piece Of Paradise On The Ocean In Key West

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Truman Annex Best Location in Town, holiday rental in Key West

Truman Annex Best Location in Town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Tropical Key West Get Away, holiday rental in Key West

Tropical Key West Get Away

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!, holiday rental in Key West

'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Truman Annex, two blocks from Duval, holiday rental in Key West

Truman Annex, two blocks from Duval

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
BEST DEAL IN THE KEYS!, holiday rental in Key West

BEST DEAL IN THE KEYS!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Craig & Cindy Key West Truman Annex 212 Fleming House, holiday rental in Key West

Craig & Cindy Key West Truman Annex 212 Fleming House

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!, holiday rental in Key West

'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, holiday rental in Key West

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ocean View Estate with Private Pool 15 minutes from Key West, holiday rental in Key West

Ocean View Estate with Private Pool 15 minutes from Key West

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!, holiday rental in Key West

'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
New Listing Family Friendly, holiday rental in Key West

New Listing Family Friendly

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, holiday rental in Key West

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Golf Club - Completely Renovated - Tree House Too., holiday rental in Key West

Key West Golf Club - Completely Renovated - Tree House Too.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Previous
Frequently Asked Questions about Key West