Key West Vacation Rentals

Search the best Key West vacation rentals, including boutique homes, cottages, and condos. Our luxury properties have spacious interiors, ideal locations, and unbeatable amenities. We offer stays from nightly to monthly, and even have a collection of pet-friendly vacation rentals. Book directly with Historic Key West Vacation Rentals for the guaranteed best rate on your vacation.

291 S

Ashe House - Monthly Rental

1223 S

Azur Palm-Oceanfront Monthly Rental

67 S

Bahari House, Seaport- Monthly Rental

1268 S

Blue Haven- NEW Monthly Rental

364 S

Butterfly Cottage - Nightly Rental

1359 S

California Dreaming - Monthly Rental

1004 S

Casablanca - Nightly Rental

332 S

Casablanca Grande - Nightly Rental

1436 S

Casablanca Too - Nightly Rental

644 S

Chavez House - Nightly Rental

720 S

Chick-a-Pea Cottage - Nightly Rental

421 S

Cloud 9 - Nightly Rental

20 S

Copa Cabana - Monthly Rental

878 S

Dreaming on Duval - Nightly Rental

1126 S

Fair Winds at the Foundry - Weekly Rental

458 S

Grand Maison - Nightly Rental

2135 S

Hibiscus Cottage-NEW Nightly Rental

589 S

Horse Conch - Nightly Rental

44 S

Inn Cogneato Cottage - Monthly Rental

129 S

La Casita en Cima- NEW Monthly Rental

614 S

La Maisonnette, Nightly Rental

787 S

Lilly's Pad- Nightly Rental

545 S

Maisons de Luxe - Nightly Group Rental

2554 S

Margarita Cottage- NEW Nightly Rental

256 S

Miss Sunshine-Monthly Rental

194 S

My Happy Place - Monthly Rental

1640 S

Palm Hideaway-NEW Monthly Rental

1078 S

Petite Maison - Nightly Rental

962 S

Poinciana Garden - Nightly Rental

1101 S

Poinciana Paradise - Group Rental

1413 S

Poinciana Treetop - Nightly Rental

1153 S

Potter's Cottage - Nightly Rental

747 S

Queen Conch - Nightly Rental

100 S

Reel Paradise - Monthly Rental

2598 S

Robinson Crusoe Cottage-NEW Nightly Rental

1 S

Rooster Conch - Nightly Rental

2576 S

Royal Poinciana Cottage- NEW Nightly Rental

1312 S

Sanctuary on South- Monthly Rental

223 S

Sea Conch - Nightly Rental

1449 S

Sea Vista - Monthly Rental

1055 S

Seas The Day! - Weekly Rental

380 S

Serene Lily - Weekly Rental

1393 S

Solaris Cottage - Nightly Rental

942 S

Solaris Garden - Nightly Rental

164 S

Solaris Pair-A-Dise - Nightly Rental

678 S

Southard Comfort - Nightly Rental

983 S

Sunny Daze Cottage- NEW Construction- Monthly Rental

2320 S

Sunset Cove- NEW Waterfront Monthly Rental

2622 S

The Conch Cottages-NEW Nightly Rental

1563 S

The Escape at Sunset Key - Monthly Rental

1026 S

The Pink House - Monthly Rental

1177 S

Three Arches in Paradise- NEW Monthly Rental

1531 S

Tropical Dream - Monthly Rental

1495 S

Villa Azul - Monthly Rental

498 S

Villa Josine - Nightly Rental

828 S

Villa Luxe - Nightly Rental

  • Key West Chamber of Commerce Logo
  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
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  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge
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