Key West, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Key West, Florida on RentalSaver.com!

Key West Rentals

Filter

Popular Areas

From $374 per night (USD)
VRBO
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
UNMATCHED ISLAND RETREAT… Tucked away within one of the island’s most impressive lanes in the Casa Marina district, this ...
From $374 per night (USD)
VRBO
From $347 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $347 per night (USD)
Expedia
From $782 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $782 per night (USD)
VRBO
From $213 per night (USD)
VRBO
**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach ...
From $213 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Red Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $321 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Steps from Duval, Shared Pool - Road's End
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Located just a stone's throw from Mile Marker Zero, "Road's End" is a charming 1-bedroom, 1.5-bath townhome in ...
From $448 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short ...
From $265 per night (USD)
VRBO
From $356 per night (USD)
Expedia
BEST TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $356 per night (USD)
Expedia
From $450 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $450 per night (USD)
VRBO
From $440 per night (USD)
Expedia
POOLSIDE HANGOVER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...
From $440 per night (USD)
Expedia
From $1420 per night (USD)
VRBO
A Place on Emma at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1420 per night (USD)
VRBO
From $373 per night (USD)
Expedia
A DUCK ON THE GREEN at the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $373 per night (USD)
Expedia
From $380 per night (USD)
VRBO
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $380 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)
VRBO
From $384 per night (USD)
VRBO
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $384 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $196 per night (USD)
Expedia
From $546 per night (USD)
VRBO
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak i ...
From $546 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $213 per night (USD)
Expedia
From $539 per night (USD)
VRBO
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $539 per night (USD)
VRBO
From $688 per night (USD)
VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space ...
From $688 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $453 per night (USD)
VRBO
From $1299 per night (USD)
Expedia
Oversized home for the whole family w/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1299 per night (USD)
Expedia
From $454 per night (USD)
VRBO
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $454 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $574 per night (USD)
VRBO
From $474 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $474 per night (USD)
VRBO
From $419 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $419 per night (USD)
Expedia
$Key West Private Home/Pool/on the Water\n\n$
From $378 per night (USD)
VRBO
Key West Private Home/Pool/on the Water\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Ub ...
From $378 per night (USD)
VRBO
From $367 per night (USD)
Expedia
GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
From $367 per night (USD)
Expedia
From $1034 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1034 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Home away from home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
From $174 per night (USD)
Expedia
From $456 per night (USD)
VRBO
ARCHIPELAGO l at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $456 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Charming 3 bedroom blocks from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $613 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Old Town Charm Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
From $299 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Luxury two floor apartment in prime location of famous Duval Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Modern & Spacious 2 story Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Sho ...
From $569 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $447 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $444 per night (USD)
VRBO
From $816 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $816 per night (USD)
VRBO
From $186 per night (USD)
Expedia
ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $186 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $318 per night (USD)
VRBO
From $936 per night (USD)
Expedia
Oceanfront 4-Bed 3-Bath home with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $936 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $416 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $267 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $480 per night (USD)
VRBO
From $373 per night (USD)
VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $373 per night (USD)
VRBO
From $3918 per night (USD)
VRBO
Takeover at the Grand Maloney
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3918 per night (USD)
VRBO
From $934 per night (USD)
Expedia
BLUE LAGOON at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $934 per night (USD)
Expedia
From $1163 per night (USD)
VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1163 per night (USD)
VRBO
From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)
VRBO
From $1672 per night (USD)
VRBO
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1672 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Sailor's Sanctuary - A Renovated Condo in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $180 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Hidden Beach - the perfect place to stay in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. ...
From $520 per night (USD)
VRBO
From $2025 per night (USD)
VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $2025 per night (USD)
VRBO
From $2337 per night (USD)
VRBO
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $2337 per night (USD)
VRBO
From $1996 per night (USD)
Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1996 per night (USD)
Expedia
From $223 per night (USD)
VRBO
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $223 per night (USD)
VRBO
From $879 per night (USD)
Expedia
ARCHIPELAGO in the Truman Annex
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $879 per night (USD)
Expedia
From $677 per night (USD)
VRBO
SUNSET DALITE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $677 per night (USD)
VRBO
From $743 per night (USD)
Expedia
AQUA BREEZE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $743 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Hidden Beach Unit 1. The perfect place to stay in Key West for less
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $538 per night (USD)
VRBO
From $470 per night (USD)
Expedia
SHADY NOOK at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll enjoy bright, ...
From $470 per night (USD)
Expedia
From $245 per night (USD)
VRBO
A PALM TREE PARADISE @ the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $245 per night (USD)
VRBO
From $418 per night (USD)
Expedia
ROYAL POINCIENA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the heart of Old Town within the sought-after Shipyard community, this inviting second-floor condo offers the ...
From $418 per night (USD)
Expedia
From $911 per night (USD)
VRBO
A GULFSTREAM DRIFT at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $911 per night (USD)
VRBO
From $563 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $563 per night (USD)
Expedia
From $720 per night (USD)
VRBO
SALTWATER ANGLER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $720 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Island Breezes at The Truman Annex in Key West@ the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $402 per night (USD)
Expedia
From $780 per night (USD)
VRBO
A HARBOUR ROOST at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $780 per night (USD)
VRBO
From $438 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $438 per night (USD)
Expedia
From $462 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful gated home is located on an oversized corner lot a few blocks from White Street Pier and Higg's Beach wit ...
From $462 per night (USD)
VRBO
From $490 per night (USD)
Expedia
**ASCENSION** @ The Truman Annex Compass Realty
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $490 per night (USD)
Expedia
From $457 per night (USD)
VRBO
DANCING PALMS at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Leave the c ...
From $457 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For Pricing
Expedia
From $614 per night (USD)
VRBO
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $614 per night (USD)
VRBO
From $743 per night (USD)
Expedia
OCEAN BREEZE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $743 per night (USD)
Expedia
From $493 per night (USD)
VRBO
SAGO PALM at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $493 per night (USD)
VRBO
From $213 per night (USD)
VRBO
Pearl in Paradise-Charming 2bed 2bath Old Town home w/ shared pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $213 per night (USD)
VRBO
From $764 per night (USD)
VRBO
Duval Square Condo-2 bedroom 2.5 bath, w/pool, parking, on Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $764 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Antigua Retreat- 2BR 2BA waterfront condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $596 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $527 per night (USD)
VRBO
From $396 per night (USD)
VRBO
A Slice of Paradise! @ the Shipyard Palms!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $396 per night (USD)
VRBO
From $728 per night (USD)
VRBO
Beach Club #103 - Unique oceanfront living with breathtaking views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $728 per night (USD)
VRBO
From $578 per night (USD)
VRBO
Ann Street Cottage: A bright and airy home near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $578 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $377 per night (USD)
VRBO
From $409 per night (USD)
Expedia
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $409 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $471 per night (USD)
VRBO
From $780 per night (USD)
Expedia
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $780 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Tropical oasis in a former author’s retreat. Sleeps 4.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfect monthly r ...
From $354 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $474 per night (USD)
Expedia
From $1021 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1021 per night (USD)
VRBO
From $680 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $680 per night (USD)
VRBO
From $702 per night (USD)
VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $702 per night (USD)
VRBO
From $653 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
28 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $653 per night (USD)
VRBO
From $598 per night (USD)
VRBO
CASABELLA@DUVAL SQUARE Lovely 2 Bedroom 2.5 Bath Townhome in a great location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool a ...
From $598 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $453 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $409 per night (USD)
VRBO
From $747 per night (USD)
Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $747 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nice quiet landing a few blocks from the action on Duval Street. This is a Saturday-Saturday weekly home for the rest of ...
From $299 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Waterfront 4 Bed 4 Bath Home in Key Cove Landings
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $783 per night (USD)
Expedia
From $288 per night (USD)
VRBO
GOLF VILLA - Monthly Rental - 2BD/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $288 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)
Expedia

Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals