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From $304 per night (USD)
VRBO
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Immerse yourself in the serenity of island life with this spacious second-floor pool-view suite thoughtfully designed to ...
From $304 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, com ...
From $304 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This spacious suite offers comfort and convenience and is located on the ground floor with a pool and partial ocean view ...
From $304 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Island Time Starts Here: Cozy Ground Floor Suite in Islamorada
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Start your day with coffee on your private patio, soaking in the fresh sea breeze as you plan your Florida Keys adventur ...
From $304 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Anchor Here: Oceanfront 1BR Condo with Marina Access
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed ...
From $304 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Stay Salty: Keys Dreams 1BR Condo Steps from the Sand
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax ...
From $304 per night (USD)
Expedia
From $211 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 $211 per night (USD)
VRBO
From $424 per night (USD)
Expedia
LOCATION, LOCATION, 7th Street, you wont be disappointed with home + Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for a top-rated vacation rental in beautiful Key Colony Beach, Florida? Amberjack House is the spot! Included ...
From $424 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Keys Please is a 2bed/2bath condo located in desirable Key Colony Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Keys Please is a 2bed/2bath condo located in desirable Key Colony Beach. The complex is right on the water with its own ...
From $207 per night (USD)
VRBO
From $211 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. This ...
From $211 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Gypsy's Palace at the Truman Annex in Key West
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 $369 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Stay in Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2/2 Cozy keys home in a quiet neighborhood. Close to many restaurants, bars, shopping, beaches and many other activities ...
From $168 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Direct Oceanfront Corner Condo, WiFi, Pool, Gym, Panoramic Ocean Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FOR VIEW LOVERS and a favorite of returning visitors. EVERY ROOM has a gorgeous OCEAN view. Enjoy this rare Licensed I ...
From $301 per night (USD)
VRBO
From $506 per night (USD)
Expedia
WATERFRONT, VIEWS, HEATED POOL, 130 ft. OF DOCK, PRIVATE RETREAT
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
BOOT KEY RETREAT - OPEN WATER VIEWS - Not your typical canal house, there is plenty of privacy here. You'll be in yo ...
From $506 per night (USD)
Expedia
From $339 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 $339 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Penthouse Apartment Sunsets in Key Largo, Kawama Yacht Club Tower
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the panoramic view this tropically decorated, fifth-story penthouse unit has to offer of the Atlantic Ocean and th ...
From $279 per night (USD)
Expedia
From $809 per night (USD)
VRBO
Duck Key Tarpon House 5 Bedroom 3 Baths Duck Key w/45 Dock and Private Pool boat lift available
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Duck Key Tarpon House Exquisite Home on Duck Key with 5 bedrooms and 3 baths with Cabrera Marble Countertops and brand ...
From $809 per night (USD)
VRBO
From $843 per night (USD)
Expedia
Waterfront 4 Bed Home w/Pool – Marlin Bay
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 $843 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Vista Marquesa 4/3 Ground Level Home w/ Pool & 50` Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Vaca-23-231 Friday to Friday Booking only( We will not honor any bookings that do not follow the Friday booking unless ...
From $614 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Waterfront luxury Villa (21) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This spacious 3-bedroom, 2.5-bath Villa blends comfort with coastal charm. Each bedroom includes its own TV, and the liv ...
From $546 per night (USD)
Expedia
From $805 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + Last Key White Glove Service...
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 $805 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Knee Deep in the Water Somewhere...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The only worry if the tide's reaching your chair! Come on in The waters nice (there's a dock for a 32' boat right out ...
From $298 per night (USD)
Expedia
From $238 per night (USD)
VRBO
P16 - Charming 2 bedroom 2 bath waterfront duplex with Cabana Club.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this all ground level 2 bedroo ...
From $238 per night (USD)
VRBO
From $725 per night (USD)
Expedia
KEY LARGO WEEKLY PARADISE HOUSE RENTAL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Private Gated Community with Direct Ocean Access home. 2 bedroom, 2 bathrooms, comfortably furnished with an open floor ...
From $725 per night (USD)
Expedia
From $762 per night (USD)
VRBO
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 $762 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Pickleball & Pool Vacation at Sombrero Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and stay at our beautiful 3 bed/2ba home, with plenty of space to park your vacation water toys (boats, jetskis, et ...
From $406 per night (USD)
VRBO
From $442 per night (USD)
VRBO
Sky Loft - Steps from Duval Street & Shared Pool
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 Du ...
From $442 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful Beach Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
Click For Pricing
Expedia
From $400 per night (USD)
VRBO
Canal Front Retreat with Pool + Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The MAD MAHI is a charming waterfront condo featuring one bedroom (sleeps 4), one bathroom, a full kitchen, and a privat ...
From $400 per night (USD)
VRBO
From $2946 per night (USD)
Expedia
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 $2946 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Key Colony Beach Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The property is a 2 bedroom, 2 bath over 1,200 square feet very open floor plan home where you can enjoy this wonderful ...
From $315 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Rose All Day updated 2bed/2bath half duplex in Kcb with dockage & Cabana Club access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Rose All Day is a stunning updated 2bed/2bath half duplex in Key Colony Beach. The property features dockage, cabana clu ...
From $327 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Key Largo gem on the water with a little slice of heaven!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New waterfront CBS home on a beautiful 200 ft wide basin (not a canal) with immediate access to the bay. Mature lands ...
From $309 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Accommodations: Condominium, 2 Bedroom, 2 Bath (Sleeps 4) This is one of the finest destinations in the Florida Keys. ...
From $412 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $245 per night (USD)
VRBO
From $476 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 $476 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Tiki Time! Private Pool~Tiki Hut~Kayak~Grill~Ocean View!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a fami ...
From $267 per night (USD)
VRBO
From $225 per night (USD)
Expedia
50’ dock on Vaca Cut, deep wide unlimited dockage.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
One bedroom and one 1/2 baths nicely decorated. Cute and super clean. Tile floors throughout. Kitchen fully equipped. Wi ...
From $225 per night (USD)
Expedia
From $379 per night (USD)
VRBO
3/2 Waterfront / Private Dock / Cabana Club Pool & Beach / Kayaks / Tiki Hut 🏝.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**IMPORTANT: RENTAL IS SATURDAY TO SATURDAY ONLY, UNLESS APPROVED BY OWNER** The Starfish House is walking distance to ...
From $379 per night (USD)
VRBO
From $1698 per night (USD)
Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + Last Key White Glove Service...
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 $1698 per night (USD)
Expedia
From $315 per night (USD)
VRBO
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 $315 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Luxury Condo at Ocean Front Kawama Tower Complex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy your Key Largo stay in a private gated oceanfront community. This 3rd floor 2-bed 2-bath condo boasts approx. 1350 ...
From $396 per night (USD)
Expedia
From $2250 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 $2250 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Lock in summer months. For up to date availability 510-381-5000
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A beautifully appointed home with all the amenities you will need to have an enjoyable vacation. The first thing you wil ...
From $417 per night (USD)
Expedia
From $1996 per night (USD)
VRBO
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)
VRBO
From $337 per night (USD)
VRBO
Odisa Key Largo Vacation Home with Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Odisa Key Largo Vacation Home! Nestled in the heart of the stunning Port Largo community, this beautiful tw ...
From $337 per night (USD)
VRBO
From $583 per night (USD)
VRBO
Houseboat offers a rooftop deck for stunning views of the sunrise and sunset.
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
The Manatee houseboat has 1 King bed and 3 Double beds. Each houseboat has flat-screen TVs with cable and complimentary ...
From $583 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Archipelago at the Truman Annex in Key West
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 $551 per night (USD)
Expedia
From $662 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 condo ...
From $662 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This property has 2 bedrooms 2 baths and sleeps 6 with all updated appliances furniture.& wifi There are 4 single kayaks ...
From $391 per night (USD)
Expedia
From $492 per night (USD)
VRBO
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 $492 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Shady Nook at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This first floor 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll en ...
From $211 per night (USD)
Expedia
From $302 per night (USD)
VRBO
A Palm Tree Paradise @ the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Palm tree Paradise - Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and re ...
From $302 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Royal Poinciana >>WEEKLY RENTAL! Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WEEKLY RENTAL - This property has the ability to be rented weekly all year long. Nestled in the heart of Old Town Key We ...
From $464 per night (USD)
Expedia
From $670 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 $670 per night (USD)
VRBO
From $406 per night (USD)
Expedia
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ALL NEW RENOVATIONS COMPLETED JUST FOR YOU! A perfect oasis with beautiful views all day, every day. Come enjoy your tim ...
From $406 per night (USD)
Expedia
From $286 per night (USD)
VRBO
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 $286 per night (USD)
VRBO
From $415 per night (USD)
Expedia
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 $415 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Island Breezes at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
WEEKLY RENTAL - This property has the ability to be rented weekly. This charming second floor condominium features two b ...
From $536 per night (USD)
VRBO
From $482 per night (USD)
Expedia
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 $482 per night (USD)
Expedia
From $212 per night (USD)
VRBO
A Sanctuary Home at the Key West Golf Club in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Sanctuary Home - Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort ...
From $212 per night (USD)
VRBO
From $414 per night (USD)
Expedia
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Be Still – Your Private Island Oasis in Key West Nestled on an oversized corner lot just a few blocks from W ...
From $414 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Waterfront House in the heart of Cudjoe Key.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Breathtaking sunset views! Fully stocked kitchen with all appliances you need for at home cooking. Spacious rooms with d ...
From $567 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Ascension at the Truman Annex in Key West
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 $337 per night (USD)
Expedia
From $355 per night (USD)
VRBO
DANCING PALMS @ 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. Convenientl ...
From $355 per night (USD)
VRBO
From $566 per night (USD)
Expedia
4 Bedroom 3 Full Bath Home on Canal in Marathon w/Private 35 foot dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
4 Bedroom 3 Full Bath Home on the Canal in Marathon, a 15 minute boat ride to the ocean. Private Heated Pool. Private 35 ...
From $566 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Perfect little paradise spot in key largo Florida. (lot 15)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable mobile home, 2 bedrooms with capacity to sleep 5 plus sofa bed in living area as well. Mobile home is locate ...
From $257 per night (USD)
VRBO
From $482 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 $482 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This modern and beautifully decorated vacation rental is the perfect spot for your next family vacation or couples` geta ...
From $605 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Dock, Pool, FREE RAMP, Kayaks, Jacuzzi, Amazing Ocean Views Pets are Welcomed!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to this beautiful, newly constructed vacation home in Marathon, Florida. With its modern design and a newly inst ...
From $278 per night (USD)
VRBO
From $401 per night (USD)
Expedia
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 $401 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Sunrise Suite with Unobstructed Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy the ultimate Florida Keys getaway at Ocean Pointe 4315, a stunning oceanfront condo in Tavernier. Wake u ...
From $327 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Key largo Kawama Villa N2
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the ...
From $513 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Hidden gem in Key Largo, bunk room, outdoor kitchen, 2 pools, laundry, 2 beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This hidden gem is anything but ordinary! Come enjoy a piece of paradise in Key Largo while you relax in this spacious N ...
From $334 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close t ...
From $486 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Waterfront villa Family Friendly 2 bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Driftwood Villa.This newly renovated 2 bed 1.5 bath luxury villa is located in the popular area duck key alon ...
From $703 per night (USD)
VRBO
From $649 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 $649 per night (USD)
VRBO
From $239 per night (USD)
VRBO
New House Paradise Without a Pasport On Atlantic Ocean Deck Sunsets Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possib ...
From $239 per night (USD)
VRBO
From $680 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 $680 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Waterfront Luxury Home with Private Dock, Pool & Ramp
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
About the property *** CONTACT ME DIRECTLY FOR SPECIAL RATES ON DATES YOU MAY BE INTERESTED IN. ASK FOR TANIA at 786-486 ...
From $314 per night (USD)
VRBO
From $507 per night (USD)
Expedia
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come and be one of the first guests to stay in this totally remodeled modern coastal home in the heart of Key Largo, mi ...
From $507 per night (USD)
Expedia
Click For Pricing
VRBO
Big Pine Latitude Adjustment
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: Welcome to Big Pine Latitude Adjustment, a beautifully remodeled 5-bedroom, 3-bath waterfront retreat for up t ...
Click For Pricing
VRBO
From $253 per night (USD)
Expedia
Camp Mango | 2 bed/2 bath condo w/dockage, pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Camp Mango: 2 bed/2 bath condo w/ boat slip & community pool The Space: Camp Mango is a relaxed, ground-fl ...
From $253 per night (USD)
Expedia
From $661 per night (USD)
VRBO
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Boli Townhouse is an extraordinary WEEKLY rental property that you will enjoy with only a short walk to Old Town and the ...
From $661 per night (USD)
VRBO
From $747 per night (USD)
Expedia
**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...
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 $747 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Fish, Swim, Relax, Party - 4bd, 3ba - 75’ Dockage & Private POOL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DOWNSTAIRS NOW AVAILABLE! Our 4/3 Beautiful Two Story Home is in Marathon Fl. Located in the middle of the Florida Keys ...
From $471 per night (USD)
VRBO
From $273 per night (USD)
Expedia
The Garden Villa – Cozy 1BR Ground-Level Half Duplex with Private Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Garden Villa is a stunning 1bed/1bath unit with its own private pool. This unit has fresh paint, all new furniture a ...
From $273 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Tropical Breezes is a spacious 3bed/2bath half duplex in desirable Key Colony Beach with dockage & Cabana Club access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Tropical Breezes is a spacious 3bed/2bath beautifully decorated half duplex in desirable Key Colony Beach. There is a br ...
From $404 per night (USD)
VRBO
From $1156 per night (USD)
Expedia
OCEANFRONT POOL HOUSE WITH 5 BEDROOM 3 BATH, SLEEPS 12 GUESTS.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Breathtaking sunset views from this open water home. Large dock with room for two large boats. Every night a unique su ...
From $1156 per night (USD)
Expedia
From $493 per night (USD)
VRBO
2405 Ocean Pointe Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely 2-bedroom oceanview condo in Ocean Pointe Resort is a delight! Located on the 4th floor allows the guest to ...
From $493 per night (USD)
VRBO
From $219 per night (USD)
VRBO
Newly Remodeled Corner House on the Water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-be ...
From $219 per night (USD)
VRBO
From $754 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 $754 per night (USD)
VRBO
From $822 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
29 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $822 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Sunshine and Sandbars Waterfront Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Experience the ultimate island getaway at Ocean Pointe 2302, a charming Tavernier condominium. Perfectly situa ...
From $417 per night (USD)
VRBO
From $760 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 $760 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Our Happy Place on the BEACH!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Our Happy Place – Your Perfect Beachfront Escape! If you’re looking for a serene getaway just 100 steps from ...
From $227 per night (USD)
VRBO
From $397 per night (USD)
VRBO
3 Story Waterfront House with a pool and Beautiful Views!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
***NEW POOL***29 DAYS MINIMUM STAY. Bring your boat (20,000 Lbs. boat lift). This is a family-friendly Home. Equipped wi ...
From $397 per night (USD)
VRBO
From $863 per night (USD)
VRBO
P71 - 7 bed, 6 bath up/down duplex in Key Colony!
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Great Up/Down duplex in the very desirable Key Colony Beach! This well-appointed 7 bedroom, 6 bath duplex home has room ...
From $863 per night (USD)
VRBO
From $667 per night (USD)
Expedia
P45 - Spacious 5 bedroom, 5 bath home with spectacular open water views.
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
This spacious 5 bedroom, 5 bath home boasts spectacular open water views, abundant outdoor living space and a peaceful l ...
From $667 per night (USD)
Expedia

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