Key West Vacation Rentals

You are here

Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 49 - 60 of 70 rentals matching your search criteria
Map View
List View

Papaya Place

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean!

City Cay

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
2 Guests

Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place!

Newton's Nest

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
2 Guests

Newton's Nest is a quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence.

Easy Livin'

Type

  • House
Old Town
3 Bedrooms
4 Baths
8 Guests

Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

Spa Oasis

Type

  • House
Stock Island
3 Bedrooms
2 Baths
6 Guests

Welcome to a golfer’s paradise at Spa Oasis!

Linger Longer

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Just imagine stepping out of the rental and stepping right into the pool!

Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath, 2-story town home, located in the President's Walk of Truman Annex.

Emma's Secret

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

Conch Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals. A two-bedroom, two-bath condo, second floor condo in Truman Annex.

Key West Charming

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!

Ecco Domani

Type

  • House
Old Town
3 Bedrooms
2.5 Baths
6 Guests

A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.

Buena Vista

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

Beach House Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

Pages