Key West Rentals
- From $211 per night (USD)
VRBO
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location, Location, LOCATION!!! Perfectly located in Old Town Key West, this beautifully remodeled 3 bedroom, 2 bathroom ...
From $211 per night (USD)VRBO
- From $320 per night (USD)
Expedia
A PEACE OF PARADISE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $320 per night (USD)Expedia
- From $898 per night (USD)
VRBO
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $898 per night (USD)VRBO
- From $399 per night (USD)
Expedia
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $399 per night (USD)Expedia
- From $152 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $152 per night (USD)VRBO
- From $552 per night (USD)
VRBO
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
'The Plantation' is a NO SMOKING or VAPING,3 bed 3 bath townhome located within the gated community of Truman Annex in K ...
From $552 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Roosters Perch at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $299 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Atlantic Ocean view across from Smathers Beach - La Brisa - Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open floor plan, 2 bedroom, 2 bath condo at La Brisa. Gated condo community. Large deep pool with saunas in the pool b ...
From $250 per night (USD)Expedia
- From $112 per night (USD)
VRBO
One bedroom in the heart of downtown w\/ kitchen
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Truman @ Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $112 per night (USD)VRBO
- From $400 per night (USD)
Expedia
The Secret Grotto
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Secret Grotto! This spacious 3,220 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $400 per night (USD)Expedia
- From $700 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $700 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $300 per night (USD)Expedia
- From $1028 per night (USD)
VRBO
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1028 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Oceanfront Condo at Hyatt Windward Pointe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
From $700 per night (USD)Expedia
- From $148 per night (USD)
VRBO
May 3 ngt. mid-wk..spec.\nclose beach full kitchen & patio\n139.ngt + extras\n\n\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $148 per night (USD)VRBO
- From $908 per night (USD)
Expedia
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $908 per night (USD)Expedia
- From $1786 per night (USD)
VRBO
3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $1786 per night (USD)VRBO
- From $1820 per night (USD)
Expedia
Southern Comfort: Luxury Waterfront Home with private pool & lush landscaping
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1820 per night (USD)Expedia
- From $1814 per night (USD)
VRBO
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $1814 per night (USD)VRBO
- From $1294 per night (USD)
Expedia
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1294 per night (USD)Expedia
- From $1099 per night (USD)
VRBO
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1099 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Spec. April.19-24\n155.00 night plus extras\nNear beach& Full Kitchen\n& Patio\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in the surf. Come soak up the ...
From $139 per night (USD)Expedia
- From $714 per night (USD)
VRBO
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $714 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Pierre's Perch by Brightwild | Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to the Pierre's Perch - a recently renovated, budget-friendly studio a part of history laden Galleria S ...
From $246 per night (USD)VRBO
- From $224 per night (USD)
Expedia
Chagall's Studio by Brightwild | Newly Remodeled!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to Chagall's Studio, a hidden little gem located at The Galleria Guesthouse in the heart of Bahama Vill ...
From $224 per night (USD)Expedia
- From $1836 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1836 per night (USD)VRBO
- From $2423 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2423 per night (USD)VRBO
- Click For Pricing
VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
Click For PricingVRBO
- From $594 per night (USD)
VRBO
Large 2\/2 Waterfront Condo Great View Pool & Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $594 per night (USD)VRBO
- From $621 per night (USD)
VRBO
Downtown Waterfront 2\/2 Dock & Pool Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $621 per night (USD)VRBO
- From $1408 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1408 per night (USD)VRBO
- From $589 per night (USD)
VRBO
2\/2 Fully Updated Old Town Waterfront Corner Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $589 per night (USD)VRBO
- Click For Pricing
Expedia
Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For PricingExpedia
- From $475 per night (USD)
VRBO
Hidden Oasis | Gorgeous Home, w\/ Pvt Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $475 per night (USD)VRBO
- From $249 per night (USD)
Expedia
**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ISLAND BLISS ...
From $249 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Charming, updated home near Duval St. with enclosed patio & walkable location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $293 per night (USD)VRBO
- Click For Pricing
Expedia
Old Town Conch Cottage completely remodelled and updated
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Old Town, this rare home has it all. 3 Bedrooms with 3.5 Baths in the Main House. Completed ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- Click For Pricing
Expedia
Tropical hidden gem behind Hemingway's House.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Andrew's Inn is a superbly situated tropical boutique Guesthouse where time slows in tune with the island's relaxed esse ...
Click For PricingExpedia
- From $332 per night (USD)
VRBO
2 Bedroom Townhome on Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $332 per night (USD)VRBO
- From $1292 per night (USD)
VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1292 per night (USD)VRBO
- From $511 per night (USD)
VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $511 per night (USD)VRBO
- From $1114 per night (USD)
VRBO
Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1114 per night (USD)VRBO
- From $224 per night (USD)
VRBO
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $224 per night (USD)VRBO
- From $393 per night (USD)
Expedia
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN MAJEST ...
From $393 per night (USD)Expedia
- From $189 per night (USD)
VRBO
The Elizabeth #1 Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $189 per night (USD)VRBO
- From $213 per night (USD)
VRBO
The Fleming #3 Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $213 per night (USD)VRBO
- From $235 per night (USD)
VRBO
New Listing-Golf Course Charmer!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
From $235 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
From $315 per night (USD)Expedia
- From $299 per night (USD)
VRBO
The Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Bed)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $299 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Room 2 (1 Queen Bed & Single Sleeper Sofa)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $299 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Speakeasy Inn -Room 1B-1 Queen Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $289 per night (USD)VRBO
- From $459 per night (USD)
VRBO
Starr's Suite - 2 person K Suite w\/Private Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $459 per night (USD)VRBO
- From $175 per night (USD)
VRBO
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of va ...
From $175 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Breezy Key West 1st-Floor Condo w\/ Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $138 per night (USD)Expedia
- From $266 per night (USD)
VRBO
**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $266 per night (USD)VRBO
- From $500 per night (USD)
VRBO
BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegantly renovated and furnished with guest comfort and enjoyment in mind we would like to welcome you to “Be as you ar ...
From $500 per night (USD)VRBO
- From $166 per night (USD)
VRBO
Poolside tropical paradise in Key West! The Salty Conch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...
From $166 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $292 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Our Piece of Paradise-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $375 per night (USD)VRBO
- From $294 per night (USD)
Expedia
Midnight Cowboy by AvantStay | 3 Artistic Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $294 per night (USD)Expedia
- From $143 per night (USD)
VRBO
Monkey House by AvantStay | Pool, by Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $143 per night (USD)VRBO
- From $156 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $156 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Speakeasy Inn - 1C (1 Queen Bed & Sleeper Sofa)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $299 per night (USD)VRBO
- From $289 per night (USD)
Expedia
Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Sleeper Sofa)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $289 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Rum Cay\/ 2 bedroom 2 bath Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rum Cay offers a quiet alternative to the downtown area of Key West. Located a short 10-minute ride away from the nightl ...
From $360 per night (USD)VRBO
- Click For Pricing
VRBO
Hyatt Residence Club, Beach House, Two Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A tropical getaway in classic Key West style Escape to a Florida destination renowned for its hospitality and relaxed ...
Click For PricingVRBO
- From $377 per night (USD)
VRBO
1st year for this gorgeous 4Bd 4Ba all ensuite, 2 parking spots, backyard oasis!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Moveable Feast, a new monthly vacation rental in the heart of Bahama Village that sleeps 10 comfortably. Loca ...
From $377 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Old Town Key West Home w\/ Deck < 1 Mi to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ensure your next stop in Key West includes easy access to all of the island’s most iconic attractions when you book this ...
From $139 per night (USD)Expedia
- From $595 per night (USD)
VRBO
KAMP by Brightwild | Rooftop Penthouse On Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $595 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottage ...
From $448 per night (USD)VRBO
- From $413 per night (USD)
VRBO
Key West Lighthouse Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Key West Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites Collection, is a 5-star, 1 ...
From $413 per night (USD)VRBO
- From $345 per night (USD)
Expedia
American Shoal Suite | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unexpected Location The American Shoal Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites ...
From $345 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Tortugas Harbor Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unexpected Location The Tortugas Harbor Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suite ...
From $380 per night (USD)VRBO
- From $371 per night (USD)
Expedia
Sombrero Suite | 1 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unexpected Location The Sombrero Reef Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites ...
From $371 per night (USD)Expedia
- From $388 per night (USD)
VRBO
Alligator Reef Suite | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Alligator Reef Suite, a beautiful 2 bedroom vacation rental property located just half a block from Duval ...
From $388 per night (USD)VRBO
- From $283 per night (USD)
VRBO
L` Attitude Adjustment | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Dream Getaway in Key West, Florida! Discover the ultimate monthly vacation rental in Key West. This stun ...
From $283 per night (USD)VRBO
- From $919 per night (USD)
VRBO
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $919 per night (USD)VRBO
- From $624 per night (USD)
Expedia
Custom House Inn | Two 2nd Floor Suites On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $624 per night (USD)Expedia
- From $605 per night (USD)
VRBO
Custom House Inn | Two Suites On Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $605 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Delancey Hall in Old Town with a pool and privacy!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local and walk or bike to town. Enjoy your large furnished front porch or your own private back porch by the ...
From $500 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Studio Unit in quiet resort adjacent to Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
From $250 per night (USD)VRBO
- From $375 per night (USD)
Expedia
NEW! Atlantic Oasis | Heated Pool, Near Beach!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Atlantic Oasis is a true Key West "Conch Style" townhome consisting of over 1900 sq. ft. of beautiful living sp ...
From $375 per night (USD)Expedia
- From $376 per night (USD)
VRBO
Escape to \"Casa Escondida\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $376 per night (USD)VRBO
- From $262 per night (USD)
VRBO
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
BAHAMA VILLAGE BEAUTY... This dream of a home is yours for the ultimate escape to southernmost paradise! Located in the ...
From $262 per night (USD)VRBO
- From $478 per night (USD)
VRBO
POCKETFUL OF SUNSHINE ~ Renovated 5 BR\/5.5 Ba Midtown Home w\/ Pool!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $478 per night (USD)VRBO
- From $218 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $218 per night (USD)VRBO
- From $233 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $233 per night (USD)VRBO
- From $888 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500-$1000 (approx) can be ...
From $888 per night (USD)VRBO
- From $657 per night (USD)
VRBO
NEW Spacious 2\/2 Waterfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $657 per night (USD)VRBO
- From $607 per night (USD)
VRBO
OASIS SOUTH~Opening Rates in this Stunning 5 BR\/3 Ba w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $607 per night (USD)VRBO
- From $443 per night (USD)
VRBO
McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $443 per night (USD)VRBO
- From $6158 per night (USD)
VRBO
CHANGES IN LATITUDES ~ Renovated 3 BR\/2.5 Ba Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
MODERN MERGES WITH HISTORIC CHARM... Discover a blend of sleek contemporary elegance that interweaves with the rich tape ...
From $6158 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $179 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Resort, New Year’s Eve, Hyatt, 2 Nights, Sleeps 6, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key W ...
Click For PricingVRBO