
Florida Keys Rentals

- From $2082 per night (USD)
VRBO
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Resembling a ...
From $2082 per night (USD)VRBO
- From $482 per night (USD)
Expedia
Family home in gated community w/great amenities, shared pool, fitness center
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hemingway Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $482 per night (USD)Expedia
- From $458 per night (USD)
VRBO
Sombrero Beach Villa with Private Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This beautiful villa was built in 2017, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $458 per night (USD)VRBO
- Click For Pricing
Expedia
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingExpedia
- From $226 per night (USD)
VRBO
Comfortable Waterfront Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guests must register at the office unless it is after hours in which you will register at the Guard House. Unit 175 is c ...
From $226 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2/1.5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)Expedia
- From $585 per night (USD)
VRBO
208 Mariners Club Key Largo | 3 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated! This tri-level townhouse has a laid-back, welcoming Florida Keys vibe, pristine decor, sleek new kitch ...
From $585 per night (USD)VRBO
- From $581 per night (USD)
Expedia
Marina Villa 212 3/3 Pools, Marina and Ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Best vacation rental to explore the Florida keys. Marina Villa 212 (3b/3b) with Marina and ocean views. Escape to pa ...
From $581 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Fins to the Left 2 bed 2 bath Duplex w/ Cabana Club & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy some changes in attitude and latitude in this waterfront beauty! This is a two bedroom, two bath, stilted, one-hal ...
From $366 per night (USD)VRBO
- From $476 per night (USD)
Expedia
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You will know you're on vacation when you enter this luxurious townhome! This beautiful home is located in Kawama Yacht ...
From $476 per night (USD)Expedia
- From $387 per night (USD)
VRBO
Vacation Home on Open Gulf with Fantastic Panoramic View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our home in Marathon at M.M.51, is located in a tropical setting on the open gulf surrounded by lush palms. Marathon is ...
From $387 per night (USD)VRBO
- From $1377 per night (USD)
Expedia
Gated Vacation Oasis Luxury Home Sunset Point Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to a one of a kind gated vacation oasis and experience the relaxing breezes of the bay from every room and around ...
From $1377 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Key Colony Beach Now booking for 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This unit is perfect for snowbirds seeking a fabulous winter retreat for fishing boating and other activities as well ...
From $240 per night (USD)VRBO
- From $464 per night (USD)
Expedia
Waterfront Half-Duplex with 30-Ft. Dock, Sitting Pool, and Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $464 per night (USD)Expedia
- From $152 per night (USD)
VRBO
Key Largo Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The property is located in Pirates Cove (mile marker 99 bayside), which is an early Key Largo development that is quiet ...
From $152 per night (USD)VRBO
- Click For Pricing
Expedia
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For PricingExpedia
- From $255 per night (USD)
VRBO
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to Villa Paradise – Your Monthly Retreat in the Florida Keys! Discover the ultimate Florida Keys getaway at Vill ...
From $255 per night (USD)VRBO
- From $286 per night (USD)
Expedia
House full of life with pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
House in Key Largo. Great Home for a big family, 5 bedrooms and 4 full baths. Jacuzzi. Pool (8x14') with a deck. Can bri ...
From $286 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $313 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $357 per night (USD)Expedia
- From $596 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $596 per night (USD)VRBO
- From $417 per night (USD)
Expedia
Great Family Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $417 per night (USD)Expedia
- From $274 per night (USD)
VRBO
Waterfront home with gorgeous patio, WiFi, gas grill, & great location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Colony Beach Waterfront Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $274 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful Home with Great Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful home in the Florida Keys, close to everything. Amazing water views and sunrises. All Key Largo activities to e ...
Click For PricingExpedia
- Click For Pricing
VRBO
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingVRBO
- From $359 per night (USD)
Expedia
water at your back door
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $359 per night (USD)Expedia
- From $924 per night (USD)
VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $924 per night (USD)VRBO
- From $484 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $484 per night (USD)Expedia
- From $527 per night (USD)
VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $527 per night (USD)VRBO
- From $436 per night (USD)
Expedia
Waterfront house with covered patio, private pool, & 75' dock - dogs welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Magic in Marathon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $436 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $340 per night (USD)VRBO
- From $306 per night (USD)
Expedia
Queen’s Lair Rockhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $306 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Seas The Day 3bed/2.5bath updated with great outdoor space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Seas the Day is a beautifully designed 3-bedroom, 2.5-bathroom townhouse-style single-family home located in the heart o ...
From $300 per night (USD)VRBO
- From $326 per night (USD)
Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $326 per night (USD)Expedia
- Click For Pricing
VRBO
Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Hueso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For PricingVRBO
- From $316 per night (USD)
Expedia
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $316 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $135 per night (USD)VRBO
- From $1243 per night (USD)
Expedia
Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beachfront Ocean Duplex Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1243 per night (USD)Expedia
- From $317 per night (USD)
VRBO
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $317 per night (USD)VRBO
- From $274 per night (USD)
Expedia
Bright & Breezy Top Floor Ocean View Condo w/ Double Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $274 per night (USD)Expedia
- From $535 per night (USD)
VRBO
Comfortable Condo with Pool, Private Balcony, & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $535 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Quiet & Stress Free canal home with private dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The home has 3 bedrooms and 2 bath. The dock has space for a boat up to 30’. Come and enjoy the beautiful surroundings ...
From $186 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $308 per night (USD)VRBO
- From $176 per night (USD)
Expedia
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $176 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Dog-friendly resort condo with pool & hot tub, private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $332 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Pool & Parking & Pet Friendly - Southernmost View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $354 per night (USD)Expedia
- From $1102 per night (USD)
VRBO
Charming dog-friendly home with guest cottage & private pool - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 2
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1102 per night (USD)VRBO
- Click For Pricing
Expedia
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For PricingExpedia
- From $633 per night (USD)
VRBO
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Amelia House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $633 per night (USD)VRBO
- From $342 per night (USD)
Expedia
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Leeward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $342 per night (USD)Expedia
- From $238 per night (USD)
VRBO
BOOK YOUR DREAM VACATION at BEACON REEF - Special deal 5/11-6/14 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SPECIAL DEAL FOR May 11-June 14 2025 ONLY!!! World Famous Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Perso ...
From $238 per night (USD)VRBO
- From $366 per night (USD)
Expedia
Beautiful vacation home in the heart of Islamorada , Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the hom ...
From $366 per night (USD)Expedia
- From $624 per night (USD)
VRBO
Bright condo with charms of historic Key West - amazing walkable locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $624 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Imagine in the Keys - Venture Out Unit 073
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine in the Keys VO073 35' Dockage Canal front 2Bd/2Ba This home features 2Bd/2Ba and is located only 3 lots from op ...
From $286 per night (USD)Expedia
- From $470 per night (USD)
VRBO
Keys Relaxing Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Have fun with the whole family at this stylish place. Explore the Florida Keys from this central location. Key Largo i ...
From $470 per night (USD)VRBO
- From $391 per night (USD)
Expedia
★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $391 per night (USD)Expedia
- From $501 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $501 per night (USD)VRBO
- From $482 per night (USD)
Expedia
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO PERFECT, far from normal! This stunning 2 bedroom, 2.5 bathroom townhouse with private pool will check all the ...
From $482 per night (USD)Expedia
- From $2397 per night (USD)
VRBO
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2397 per night (USD)VRBO
- From $1114 per night (USD)
Expedia
Boaters’ Paradise - Marlin Bay Resort & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $1114 per night (USD)Expedia
- From $287 per night (USD)
VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $287 per night (USD)VRBO
- From $194 per night (USD)
Expedia
Modern 2BR Condo Old Town/Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $354 per night (USD)VRBO
- From $197 per night (USD)
Expedia
Private Parking & Near Downtown - Lil' Bit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $197 per night (USD)Expedia
- From $346 per night (USD)
VRBO
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Palm Breeze - Villa 5030 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $346 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Kawama Yacht Club-Oceanfront Resort-Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Kawama Yacht Club, a Tropical Oceanside Resort in the heart of the Florida Keys (Oceanside Key Largo at Mile ...
From $475 per night (USD)Expedia
- From $1195 per night (USD)
VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1195 per night (USD)VRBO
- From $730 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $730 per night (USD)Expedia
- From $816 per night (USD)
VRBO
525 Mariners Club Key Largo | 4 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This sumptuous four bedroom oceanfront villa exudes luxury in every detail...the finest leather furnishings...custom woo ...
From $816 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Luxury Condominium In Key Largo... Sunsets, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
From your balcony in the Kawama Tower, you get stunning vistas of ocean and palm trees. Enjoy the view from this complet ...
From $321 per night (USD)Expedia
- From $795 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $795 per night (USD)VRBO
- From $815 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $815 per night (USD)Expedia
- From $374 per night (USD)
VRBO
BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your family will be close to everything when you stay at this centrally-located place. Our home is close to grocery stor ...
From $374 per night (USD)VRBO
- From $780 per night (USD)
Expedia
Balcony & Near Downtown - Sky Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $780 per night (USD)Expedia
- From $239 per night (USD)
VRBO
This Oceanfront Resort HAS IT ALL!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic 2 bedroom, 2 bath condo resort. Enjoy the breathtaking view of the Atlantic Ocean from the patio just steps fr ...
From $239 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Enjoy Caribbean weather in the USA. Summer openings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $223 per night (USD)Expedia
- From $759 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $759 per night (USD)VRBO
- Click For Pricing
Expedia
Mermaid Magic 3bed/3bath half duplex with dockage & Cabana Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful ground level spacious 3 bedroom 3 bathroom duplex. Updated kitchen with gorgeous wood cabinets and stainless a ...
Click For PricingExpedia
- From $663 per night (USD)
VRBO
New 4/3 Private Single Family - 2 min to ocean, kayaks, paddleboards, bicycles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Treasure at Sombrero Beach is a 2020 built single-family home on a large lot within walking distance to the beautif ...
From $663 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Beachy getaway with pool, water views, furnished patio, & dock access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
R & R Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $273 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Fairway Villa w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $332 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Splash Pool- Key Colony Villa - KCB#4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our stunning waterfront unit in Key Colony Beach with its tropical outdoor living & instant ocean access from ...
From $377 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Sunrise Escape - Ocean Front Villa - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the sunrise while sitting on one of two terraces while sipping your morning coffee in the exclusive part of Kawama ...
From $494 per night (USD)VRBO
- From $687 per night (USD)
VRBO
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $687 per night (USD)VRBO
- From $657 per night (USD)
VRBO
612 Mariners Club | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) w ...
From $657 per night (USD)VRBO
- From $278 per night (USD)
Expedia
Ocean Point Retreat ~ Immaculate Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Private Beach, Fishing Pier, Fish Cleaning Station, Jr. Olympic pool, Spa, Pickleball Court, BBQ grills, nature ...
From $278 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Coo Coo's Nest ~ Key Largo canal front 2/3 with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful pool home with dockage in the heart of Key Largo! The Space: Step into the enchanting Coo Coo's Nest ...
From $250 per night (USD)VRBO
- From $339 per night (USD)
Expedia
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $339 per night (USD)Expedia
- From $163 per night (USD)
VRBO
New Tiny House RV, Kayak, Beach, Marina, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Camper RV at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed, 1 Pull out Sofa, Single bed in Lof ...
From $163 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Light, Bright & Nautical Condo - 5 min to Local Attractions [Ocean Pointe 1211]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our beautifully designed oceanfront condo in Key Largo, nestled beside a tropical mangrove forest. The condo offer ...
From $266 per night (USD)Expedia
- From $374 per night (USD)
VRBO
Amazing Beach! Near John Pennekamp National Marine Sanctuary, 2 Outdoor Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stretch out and settle into our Resort View Junior Suite, featuring a private bedroom with a king bed and a separate liv ...
From $374 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our island oasis, Ohana Cay! We would love to welcome you to our recently updated four bedroom/four bathroom ...
From $495 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Vacation home in Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
AWESOME View of the Bay- from Chickee Hut Dock to Full Roof Top Patio. 2 Story. Large Master Bedroom with Steam Shower. ...
From $293 per night (USD)VRBO
- From $521 per night (USD)
Expedia
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + 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! The sound of ...
From $521 per night (USD)Expedia
- From $538 per night (USD)
VRBO
P03 - Charming 4 bedroom home with pool and dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home is located in the quiet and very desirable Coco Plum neighborhood, a few minutes' walk to the beach. ...
From $538 per night (USD)VRBO
- From $284 per night (USD)
Expedia
P41 - Beach Front condo with 2 bedrooms, 2 bath, pool and tennis courts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Condo overlooking the natural beach of Coco Plum. This 2 bedroom, 2 bath congo unit offers 1,280 sq feet of living space ...
From $284 per night (USD)Expedia
- From $456 per night (USD)
VRBO
P78 - Charming beach home just down the road from Sombrero Beach. 3 bedroom 2...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 minute walk ...
From $456 per night (USD)VRBO
- From $456 per night (USD)
Expedia
P27 - Private Beach Access! Pool home with everything you need for an...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, pr ...
From $456 per night (USD)Expedia
- From $316 per night (USD)
VRBO
P29 - Charming 3 bedroom 2 bath duplex with deep water dockage and Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key Colony at its most charming! This 3 bedroom, 2 bathroom, half duplex is located in the heart of Marathon in Key Colo ...
From $316 per night (USD)VRBO
- From $480 per night (USD)
Expedia
P67 - New Construction 3 bedroom 4 bath with private pool, dock and beach...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely two story duplex offers 3 bedroom, 4 bathrooms and abundant living space on both levels. The lower level off ...
From $480 per night (USD)Expedia