Florida Keys Rentals
From $162 per night (USD)VRBO
Waterfront Home with 33-Ft. Dock and Cabana Club Membership with Beach and Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Ninth Street Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $162 per night (USD)VRBO
From $240 per night (USD)Expedia
Waterfront Home w/ Private Dock, Canal Views, Large Terrace & Modern Kitchen!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $240 per night (USD)Expedia
From $237 per night (USD)VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $237 per night (USD)VRBO
From $576 per night (USD)Expedia
Two Master Suites! 35' Boat Dockage! Outdoor Living Space & Summer Kitchen!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
At Sombrero Serenity boaters will appreciate the deep water docking out back with room to accommodate up to a 35 ft. boa ...
From $576 per night (USD)Expedia
From $225 per night (USD)VRBO
Vaca Cove (C) Reel Paradise 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-22-98 No Saturday BOOKING (we will not honor anyone who books other dates without the agent's approval) Please Mes ...
From $225 per night (USD)VRBO
From $347 per night (USD)Expedia
Casa Linda Vacation Home on Water Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
Keep it simple at enjoy the amazing views at this peaceful and centrally-located duplex! The house has its own covered b ...
From $347 per night (USD)Expedia
From $521 per night (USD)VRBO
W04 - 209 Sombrero Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $521 per night (USD)VRBO
From $229 per night (USD)Expedia
Boaters Dream - 80 ft dock, Kayak-Minutes to Oceans
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This property is located at 686 25th St Oceanside,Marathon known as the gem of the keys. Boating guests are particularl ...
From $229 per night (USD)Expedia
From $533 per night (USD)VRBO
Beautiful Views, Pool, Swimup bar, Dock, Spa, Ice Machine, SUPs, Kayaks & More!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our home is a bright, open house with huge windows that look out over the Gulf of Mexico and the pool / swim up bar/ out ...
From $533 per night (USD)VRBO
From $400 per night (USD)Expedia
Keys Cottage with Beach and Dockage! Bayfront Property!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Deckhouse" is tastefully decorated with nautical-style, "beachy" decor and artwork. It has a full-size kitchen with gra ...
From $400 per night (USD)Expedia
From $167 per night (USD)VRBO
KCB 1 BD/sleeps-4+Pet friendly+WiFi+Private Cabana Club-Dock on Canal
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our waterfront home is located on 100 foot wide water canal with 30 feet of dockage. We are pet friendly. Furnished with ...
From $167 per night (USD)VRBO
From $325 per night (USD)Expedia
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has alwa ...
From $325 per night (USD)Expedia
From $400 per night (USD)VRBO
Waterfront Cottage - Beach and Dockage! Open Water Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Keys living the way it used to be! In a world of chain hotels and fabricated experiences, this little slice o ...
From $400 per night (USD)VRBO
From $350 per night (USD)Expedia
Mockingbird Pointe - Waterfront Tropical Escape - Private Home, Pool and Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $350 per night (USD)Expedia
From $200 per night (USD)VRBO
Nader's Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $200 per night (USD)VRBO
From $335 per night (USD)Expedia
P64 - 260 4th Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $335 per night (USD)Expedia
From $95 per night (USD)VRBO
Great Rates! Remodeled Cozy Waterfront Mobile Home In Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally remodeled home located at Eagle Dr in quiet Sexton Cove. 5 minutes away from John Pennekamp State Park, great r ...
From $95 per night (USD)VRBO
From $257 per night (USD)Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES NOW!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
From $257 per night (USD)Expedia
From $189 per night (USD)VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RECENTLY remodeled with beautiful Keys colors. This Lobstering paradise is just 2 houses down from open water on a deep ...
From $189 per night (USD)VRBO
From $520 per night (USD)Expedia
Vitamin Sea 4bed/3bath updated single family with pool, dockage & Cabana Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR21-000361 Your vacation awaits at Vitamin Sea in desirable Key Colony Beach! Vitamin Sea’s canal frontage boasts 60 ...
From $520 per night (USD)Expedia
From $700 per night (USD)VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 ot ...
From $700 per night (USD)VRBO
From $325 per night (USD)Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $325 per night (USD)Expedia
From $2415 per night (USD)VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $2415 per night (USD)VRBO
From $365 per night (USD)Expedia
Waterfront Home with Dock, Pool Table, & Private Pool - Walk to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $365 per night (USD)Expedia
From $500 per night (USD)VRBO
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
In response to COVID-19, our cottage will be disinfected and sanitized professionally prior to all check-ins. Professio ...
From $500 per night (USD)VRBO
From $253 per night (USD)Expedia
Ocean front building 2 br/2 ba Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything you could want for your Florida Keys vacation is here! Location, location, location is the key to your family ...
From $253 per night (USD)Expedia
From $455 per night (USD)VRBO
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $455 per night (USD)VRBO
From $700 per night (USD)Expedia
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $700 per night (USD)Expedia
From $272 per night (USD)VRBO
Spectacular open-water Sunset Views with Boat Slip, newly remodeled
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $272 per night (USD)VRBO
From $366 per night (USD)Expedia
Canal-front home remodeled for HGTV with private swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $366 per night (USD)Expedia
From $140 per night (USD)VRBO
Jolly Roger Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is the perfect Keys paradise home. It is in a friendly neighborhood close to all your needs. After a busy day on th ...
From $140 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 $387 per night (USD)VRBO
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $387 per night (USD)VRBO
From $325 per night (USD)Expedia
Waterfront Duck Key Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
From $325 per night (USD)Expedia
From $350 per night (USD)VRBO
August/September discounts - Vacation like a local
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $350 per night (USD)VRBO
From $169 per night (USD)Expedia
Natural Serenity: Gorgeous boating home on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy uninterrupted natural vistas from this gorgeous home in one of the Lower Keys' best boating neighborhoods, Pine Ch ...
From $169 per night (USD)Expedia
From $433 per night (USD)VRBO
Heated Pool, Kayaks, SUP’s, Bikes, Boat Ramp, BBQ, Fire Pit, beach chairs, more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury in Paradise! Fully remodeled from the ground up, inside and out, all new furnishings in summer of 2022. Your bu ...
From $433 per night (USD)VRBO
From $429 per night (USD)VRBO
COCONUT in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $429 per night (USD)VRBO
From $200 per night (USD)VRBO
Ocean Shores Lux-Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $200 per night (USD)VRBO
From $175 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $175 per night (USD)Expedia
From $215 per night (USD)VRBO
PEACEFUL PRIVACY PARADISE HOME W/TWO KAYAKS GOLF CART FISHING RODS,POOL, PIER
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
MOST INCREDIBLE FIND IN ALL OF THE KEYS! BEAUTIFUL HOME IN THIS GRAND GATED COMMUNITY. GORGEOUS 56 ACRE PARK, BEAUTIFU ...
From $215 per night (USD)VRBO
From $272 per night (USD)VRBO
Near Outdoor Attractions, Spacious Units, Pool and Near Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In this room, there is plenty of space to relax and stretch out. Spacious yet classically structured, the room is cozy a ...
From $272 per night (USD)VRBO
From $292 per night (USD)VRBO
Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $292 per night (USD)VRBO
From $116 per night (USD)Expedia
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
White Palm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $116 per night (USD)Expedia
From $599 per night (USD)VRBO
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + 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! When your vac ...
From $599 per night (USD)VRBO
From $544 per night (USD)Expedia
**SET SAIL @ COCONUT MALLORY** Condo + 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! SET SAIL cele ...
From $544 per night (USD)Expedia
From $200 per night (USD)VRBO
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
From $200 per night (USD)VRBO
From $1127 per night (USD)Expedia
Sun of a Beach 7bed/5bath updated single family with private pool, hot tub &
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
VACA-20-915 MUST BE 25 OR OLDER TO RENT Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 16 (NO MATTER THE AGE) Th ...
From $1127 per night (USD)Expedia
From $199 per night (USD)VRBO
Social distance, work remote (or not at all) in paradise at this beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Very flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, ...
From $199 per night (USD)VRBO
From $275 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $275 per night (USD)Expedia
From $280 per night (USD)VRBO
Comfort and Convenience! Pets Allowed, Free Parking, Tennis Courts, Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $280 per night (USD)VRBO
From $561 per night (USD)VRBO
Just What You Were Looking For! 2 Great Units, Free Parking, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $561 per night (USD)VRBO
From $343 per night (USD)VRBO
Charming and Private
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
20 Miles from Key West and mini golf, private pool & hot tub, deluxe outdoor kitchen, outdoor shower, screened in porch ...
From $343 per night (USD)VRBO
From $702 per night (USD)Expedia
NEW HOT TUB aboard Houseboat Haven & Pool Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...
From $702 per night (USD)Expedia
From $638 per night (USD)VRBO
Conspicuous bliss...136 Mariners Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Oc ...
From $638 per night (USD)VRBO
From $1039 per night (USD)Expedia
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $1039 per night (USD)Expedia
From $168 per night (USD)VRBO
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
From $168 per night (USD)VRBO
From $263 per night (USD)Expedia
Spacious 1 bedroom 1 bath ground level, studio- 610 Mariners Club
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweet studio apartment in coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground floor 1- ...
From $263 per night (USD)Expedia
From $192 per night (USD)VRBO
Canal-Front Keys Escape with WiFi, AC, W/D, Patio/Firepit/Grill, & Boat Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $192 per night (USD)VRBO
From $300 per night (USD)Expedia
Waterfront escape with dock, furnished deck & patio, grill & central AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dockside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $300 per night (USD)Expedia
From $151 per night (USD)VRBO
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tradewinds Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $151 per night (USD)VRBO
From $277 per night (USD)Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $277 per night (USD)Expedia
From $772 per night (USD)VRBO
New saltwater pool and spa with ocean views, cabana club membership and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Relax at this wonderful Key Colony beach home right at the canal entrance to the Atlantic Ocean. The home offers ocean a ...
From $772 per night (USD)VRBO
From $865 per night (USD)VRBO
Perfect Location to Key West Action! Garden View, Pool, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $865 per night (USD)VRBO
From $1195 per night (USD)VRBO
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1195 per night (USD)VRBO
From $537 per night (USD)Expedia
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $537 per night (USD)Expedia
From $1364 per night (USD)VRBO
Fantastic Stay, Best Location! Pool, Bar, Bike Rental, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1364 per night (USD)VRBO
From $2731 per night (USD)VRBO
Tropical Getaway! Pool, Bar, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2731 per night (USD)VRBO
From $893 per night (USD)VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $893 per night (USD)VRBO
From $1363 per night (USD)VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1363 per night (USD)VRBO
From $198 per night (USD)VRBO
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $198 per night (USD)VRBO
From $233 per night (USD)Expedia
Doc`s Holiday 2bed/2bath half duplex with Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-000285 MUST BE 25 OR OLDER TO RENT Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 4 (NO MATTER THE AGE) This ...
From $233 per night (USD)Expedia
From $164 per night (USD)VRBO
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $164 per night (USD)VRBO
From $325 per night (USD)Expedia
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq/ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large m ...
From $325 per night (USD)Expedia
From $230 per night (USD)VRBO
WORK, PLAY & STAY! STUNNING LOCATION, PICTURESQUE OCEAN VIEWS & SECURE WIFI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME. Relax amongst the tropical sights and sounds in this charming oce ...
From $230 per night (USD)VRBO
From $393 per night (USD)Expedia
Angler`s Paradise 2bed/2bath updated half duplex brand new pool & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VACA-22-2 MUST BE 25 OR OLDER TO RENT Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 6 (NO MATTER THE AGE) This ...
From $393 per night (USD)Expedia
From $525 per night (USD)VRBO
Florida Keys...the island life! 410 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Trip Advisor Award Winner! From your living room or master suite enjoy the expansive view of the Atlantic Ocean and a ...
From $525 per night (USD)VRBO
From $343 per night (USD)Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $343 per night (USD)Expedia
From $198 per night (USD)VRBO
Cayo Cruz Suite - Colorful Condo with Sunset View!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Paradise awaits you in this renovated, 2 bedroom/2 bathroom condo in the highly desirable community of Sunrise ...
From $198 per night (USD)VRBO
From $173 per night (USD)Expedia
Martinique Suite- Family Friendly Condo #108!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Martinique Suite is set in the beautifully landscaped Sunrise Suites community, just 10 minutes away from a ...
From $173 per night (USD)Expedia
From $120 per night (USD)VRBO
***Fun In The Sun 3 Bedroom House***FREE Boat Ramp & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come relax in Florida Keys Paradise while you enjoy the comforts of a clean new 3 bedroom house, (not a mobile home). Ce ...
From $120 per night (USD)VRBO
From $606 per night (USD)Expedia
2 bedroom accommodation in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
~~7 DAY MINIMUM~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $606 per night (USD)Expedia
From $300 per night (USD)VRBO
Oceanfront! Oceanfront! Oceanfront!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
License # VR-282 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th f ...
From $300 per night (USD)VRBO
From $250 per night (USD)VRBO
IT'S A SALT LIFE AFTER ALL @ the Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $250 per night (USD)VRBO
From $220 per night (USD)VRBO
Penthouse Views - Futura Yacht Club #604
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $220 per night (USD)VRBO
From $319 per night (USD)Expedia
Beautiful home on a quiet lane on the heart of It all. Dog friendly 🐶🐾🐶
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Freshly rehabbed shotgun style home is located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 block ...
From $319 per night (USD)Expedia
From $617 per night (USD)VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $617 per night (USD)VRBO
From $303 per night (USD)Expedia
Calusa Camp ground cottage-BOATRAMP-POOL-WI-FI <br>
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME ABOARD TO ONE OF LARGER COTTAGES ON THE CAMPGROUND. Comfortable and spacious cottage in the center of KEY LARG ...
From $303 per night (USD)Expedia
From $395 per night (USD)VRBO
OCEANFRONT,POOL,BEACH,OCEAN VIEW,FISHING PIER,FREE WI-FI,New A/C,AMAZING CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NEWSFLASH *****NO DAMAGE IN THE KEYS FROM 'IAN' ***** ***Late OWNERS SPECIAL Week of October 29th check in, November 5th ...
From $395 per night (USD)VRBO
From $305 per night (USD)Expedia
Blue Vacation Home with private heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Free one day pontoon rental if you book your vacation between 11/26 - 12/24. Contact owner to coordinate available renta ...
From $305 per night (USD)Expedia
From $575 per night (USD)VRBO
Indigo Reef Resort, Villa 2 with Complimentary Dockage - An Island Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
An unforgettable Middle Keys getaway is within reach! The open floor plan welcomes socializing between the fully-equippe ...
From $575 per night (USD)VRBO
From $340 per night (USD)Expedia
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
It truly is One of the Best Private Beaches! I can help you find the best, cheapest flights and car rentals. Palm Tree ...
From $340 per night (USD)Expedia
From $443 per night (USD)VRBO
Waterfront luxury Villa (54) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $443 per night (USD)VRBO
From $586 per night (USD)Expedia
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $586 per night (USD)Expedia
From $710 per night (USD)VRBO
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $710 per night (USD)VRBO
From $775 per night (USD)VRBO
Thanksgiving Week Available Beautiful Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This property is like having your own private resort. On the Gulf of Mexico. Million-dollar waterfront views & sunsets. ...
From $775 per night (USD)VRBO
From $206 per night (USD)VRBO
A great place to relax, fish, or even work from. 2/2 , 66 ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
From $206 per night (USD)VRBO
From $360 per night (USD)Expedia
White Vacation Home. Private heated pool, and great view of the Atlantic Ocean.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Free one day pontoon rental if you book your vacation for the week of 11/26 - 12/3. Contact owner to coordinate availabl ...
From $360 per night (USD)Expedia
From $493 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $493 per night (USD)VRBO
From $471 per night (USD)Expedia
Waterfront luxury Villa (34) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $471 per night (USD)Expedia