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Florida Keys Rentals

From $310 per night (USD)
VRBO
Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $310 per night (USD)
VRBO
From $1929 per night (USD)
Expedia
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1929 per night (USD)
Expedia
From $2485 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2485 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $398 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Dog-Friendly Home on the Water w/ Dock, Boat Access, Private Pool, & Free WiFi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Marathon Magic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $400 per night (USD)
VRBO
From $859 per night (USD)
Expedia
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Welcome to 'Sombrero Sunset House' located in the heart of Sombrero Beach in Marathon, Florida! This prime waterfront ...
From $859 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $422 per night (USD)
VRBO
From $446 per night (USD)
Expedia
122 Mariners Club Key Largo | 2 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imagine yourself in this luxury, immaculately maintained two-bedroom, two and one-half bath, 2nd-floor villa with a brea ...
From $446 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Dazzling Ocean Pointe -OP-Main
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Flor ...
From $331 per night (USD)
VRBO
Click For Pricing
Expedia
Time share week in a tropical paradise! Jan 31 - Feb 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
My loss is your gain. We can't go this year but that means you can! We are unable to visit this year so I'd like to off ...
Click For Pricing
Expedia
From $301 per night (USD)
VRBO
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)
Expedia
From $560 per night (USD)
VRBO
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $560 per night (USD)
VRBO
From $731 per night (USD)
Expedia
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
0
Bathrooms:
4
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $731 per night (USD)
Expedia
From $723 per night (USD)
VRBO
Oceanfront 4 bedroom House, Pool and Deep Water Pier!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Wow! Mesmerizing views, outstanding location, directly on the Atlantic Ocean, so close to the Ocean that you can practic ...
From $723 per night (USD)
VRBO
From $1020 per night (USD)
Expedia
La Palma Verde 4bed/4 bath with pool and dockage p
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Vaca-21-69Gorgeous Home in the heart of Marathon! Located in a 4-home gated community, La Palma Verde (The Green Palm) i ...
From $1020 per night (USD)
Expedia
From $341 per night (USD)
VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $341 per night (USD)
VRBO
From $336 per night (USD)
Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $336 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Boat Slip Available: August 25 - September 5, September 13-19, September 27 - October 10, November 8-22 Keezy Does ...
From $486 per night (USD)
VRBO
From $592 per night (USD)
Expedia
Beautiful 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
New 4 Bedroom/3 Bath Family Home with private pool and 40ft dock near Sombrero Beach, shopping & dining! This spacious ...
From $592 per night (USD)
Expedia
From $401 per night (USD)
VRBO
GORGEOUS SEA THEMED 2 STORY HOME W/ PRIVATE POOL AND BEACH ACCESS
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Beautiful new 2-Story home with balcony patio. Perfect to do some grilling and feel the salt in the air. Home was finali ...
From $401 per night (USD)
VRBO
From $355 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $355 per night (USD)
VRBO
From $330 per night (USD)
VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $330 per night (USD)
VRBO
From $580 per night (USD)
Expedia
ISLAND OASIS in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $580 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Coastal retreat with private balcony, pool, & easy beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ocean Pointe #2210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $213 per night (USD)
VRBO
Click For Pricing
Expedia
2 Bedroom, Cozy home in sunny Key Largo, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautifully decorated beach house where you can get away and disconnect for a few days with your family or for a romanti ...
Click For Pricing
Expedia
From $385 per night (USD)
VRBO
Waterfront Sunway Lagoon *Huge Private Dock*
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Marathon, home of the best fishing town in the Middle Keys. This home has an incredible 120ft boat dockage, a ...
From $385 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy RV, Ocean Boaters Fish Lodge
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Direct ocean access Camper RV at Key by the Sea. 2 Bedrooms, 1 Queen Bed, 3 Bunks, Full Kitchen and Full Bathroom, Cable ...
Click For Pricing
Expedia
From $190 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $190 per night (USD)
VRBO
From $615 per night (USD)
Expedia
~The Escape ~ Your own tropical escape on private island!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $615 per night (USD)
Expedia
From $845 per night (USD)
VRBO
P44 - 4 bed, 3 bath estate home with Southern Char
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This estate style home is breathtaking! Built in beautiful southern tradition, this home does not disappoint with 4 bedr ...
From $845 per night (USD)
VRBO
From $606 per night (USD)
Expedia
Stunning & Welcoming Pool Home on Canal
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your dream getaway in the Florida Keys! This spacious 4-bedroom, 3-bathroom waterfront home is designed for r ...
From $606 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Stay near Jimmy Johnson’s Big Chill – just a 18-min stroll away
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to the stunning shores of Key Largo and experience the ultimate island getaway at our 2-bedroom condo. Nestled ju ...
From $388 per night (USD)
VRBO
From $835 per night (USD)
Expedia
PARADISE FOUND!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Paradise Found at Mariners Club in Key Largo, FL a beautiful spacious 3-story town-home in an exclusive resort located ...
From $835 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
VRBO
From $487 per night (USD)
Expedia
4 Bedroom,4 Bath with private pool and 37 and 1/2 foot boat dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This home has 2 levels and is located at 401 9th Street in Key Colony Beach. Private Boat dock that is 37 and half feet ...
From $487 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Rx: Paradise in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the mesmerizing beauty of colorful sunsets during your vacation in this recently renovated property! Unwind o ...
From $484 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Yellow 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 $504 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Blue 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 $540 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $504 per night (USD)
Expedia
From $570 per night (USD)
VRBO
SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and no ...
From $570 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Angler's Retreat in Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy the Florida Keys in this beautifully updated 3-bedroom, 2-bath home just minutes from Sombrero Beach! The fully eq ...
From $477 per night (USD)
Expedia
From $751 per night (USD)
VRBO
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come stay with us at VENTURE OUT, a fantastic safe, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $751 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $271 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $224 per night (USD)
VRBO
From $370 per night (USD)
Expedia
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $370 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Keys Life at Ocean Pointe, Pool, Jacuzzi, Beach, Gated Resort, Baby Friendly !!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our Romeo & Juliet Suite with 2 Balconies, perfect for family fun and memory-making vacations. The master sui ...
From $314 per night (USD)
VRBO
From $702 per night (USD)
Expedia
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $702 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Ocean Jewel in Marathon
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
"Ocean Jewel" is a beautifully decorated one bedroom & one bath condo in a resort syle setting with some resort amenitie ...
From $284 per night (USD)
VRBO
From $170 per night (USD)
Expedia
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $170 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Sombrero Island Breeze 4BD Pool Paradise (M#9)
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Indulge in five-star waterfront luxury at this stunning 4BR, 3BA retreat in one of the Keys' most unique island communit ...
From $482 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Duval Street Suites on Duval Free Parking and heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $233 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Duval Street Suites full kitchen, free parking, & heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $255 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Duval Street Suites full kitchen, free parking, heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $252 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Duval Street Suites full kitchen and heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking ...
From $243 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Duval Street Suites with full kitchen heated pool, free parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duva ...
From $234 per night (USD)
Expedia
From $2736 per night (USD)
VRBO
6 BR 6 BA Guesthouse Suites on Duval free parking, private pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $2736 per night (USD)
VRBO
From $527 per night (USD)
Expedia
P60 - 4 bedroom 4 bathroom home with pool and dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style! Guests love the different theme ...
From $527 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
Great deal ! Private pool and dock. Five minute bike ride to Sombrero Beach.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3 bedroom and 3.5 bath house has everything you need in order to experience a relaxing and enjoyable vacation at S ...
From $1045 per night (USD)
VRBO
From $918 per night (USD)
Expedia
ATLANTIS...Ocean Front Cottage Retreat!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need ...
From $918 per night (USD)
Expedia
From $180 per night (USD)
VRBO
MONTHLY RENTAL, Old Town Duplex, private backyard, 2 BR/2 BA, pets ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $180 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Sunset Villas is a boutique resort boasting 4 private villas on a Bayfront acre with one of the few swimmable sandy beac ...
From $392 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Quiet canal-front 3/3 Single-Family Home with Private Pool & Cabana Club Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Blue Heron House. Enjoy and relax in our ground-level 3 bedroom / 3 bathroom private, single-family home whi ...
From $526 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Easy Ocean Access House 30' Dock & Pool at Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Beach House in the prestigious Key Colony Beach. 30 FT dock house in a 90 FT canal with easy access to th ...
From $262 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Amazing Views in Florida Keys Bayside BAY BREEZES, SUNSETS, SAILBOATS n SEAGULLS
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make memories lasting a lifetime at Anchors Aweigh - experience Bay Breezes, Sunsets, Sailboats n Seagulls with this per ...
From $671 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Tropical oasis near all the action with central AC & balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Harbor Villa 7103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $269 per night (USD)
Expedia
From $615 per night (USD)
VRBO
115 Mariners Club | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Key Largo’s coastal setting beckons from inside your marina-front villa as you enter through the front door with a spect ...
From $615 per night (USD)
VRBO
From $580 per night (USD)
Expedia
Parking, Pool, Near Duval St - Poolside Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $580 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Cozy Home!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly renovated half duplex on a quiet street in Marathon. Conveniently located in the heart of Marathon, on a canal jus ...
From $362 per night (USD)
VRBO
From $433 per night (USD)
Expedia
AWAY FROM IT ALL @ The Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $433 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Coral Lagoon #13: Pool, Water Views, off Vaca Cut with Gulf & Atlantic Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Coral Lagoon #13: Pool, Water Views, Located just off Vaca Cut with easy Gulf & Atlantic Access. ****Please note that t ...
From $539 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $619 per night (USD)
Expedia
From $334 per night (USD)
VRBO
*New Modern* 3br/2ba Duplex/37' Dock/Cabana/Kayaks/Bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfectly situated in KCB w/ 37.5 feet of dockage on a wide and pristine canal that leads easy access to both the Ocean ...
From $334 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Villa Valbuena Azul Escape Key Largo 2 Kings, Pickleball
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
<p>This property is managed by KEYLARGOTRAVELS We own several remodeled high-end units in Key Largo. Please check out al ...
From $429 per night (USD)
VRBO
From $580 per night (USD)
Expedia
P18 - Spectacular 4 bedroom home with dockage and
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This lovely 4 bedroom, 4 bath home is located in the highly desirable area of Key Colony Beach. - Maximum ...
From $580 per night (USD)
Expedia
From $2070 per night (USD)
VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $2070 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $478 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Enjoy this relaxing beachy house on a canal flowing into sexton cove bay.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy this cozy home with a beautiful water front terrace. Conveniently located close to grocery stores, great restaura ...
From $169 per night (USD)
VRBO
From $277 per night (USD)
VRBO
Vibrant Family Condo / Pool & Ocean Panorama #3
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy vibrant living at our 2-bedroom Colourful Keys Condo, where fun meets relaxation. Boasting pool and ocean views, t ...
From $277 per night (USD)
VRBO
From $485 per night (USD)
VRBO
P82 - Sombrero Beach - 4 bedroom pool home with do
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4- ...
From $485 per night (USD)
VRBO
From $701 per night (USD)
Expedia
3bed vacation ocean side townhome 2pools,marina,lagoon,golf cart,bikes,kayaks
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Family and Friends vacation in mind - beautiful Key Largo townhouse with 2 separate living rooms which that offers a un ...
From $701 per night (USD)
Expedia
From $833 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $833 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)
Expedia
From $419 per night (USD)
VRBO
Sunsets on the bay at Villa Mia
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $419 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Pet Friendly, Pool, Free Parking - The Grand Turk
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $515 per night (USD)
Expedia
From $414 per night (USD)
VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $414 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Paradise in Key Colony with Cabana Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This is a fisherman's dream rental. 3/2 half duplex in Key Colony Beach. By water 5 min. to the Atlantic and 15 min. to ...
From $360 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Reel Paradise 1 in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two bedroom two bath half duplex is recently remodeled and updated with brand new everything! The kitchen & living ...
From $348 per night (USD)
VRBO
From $625 per night (USD)
Expedia
P87 - New Construction house. 4 bedrooms, open wat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spect ...
From $625 per night (USD)
Expedia
From $111 per night (USD)
VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $111 per night (USD)
VRBO
From $1270 per night (USD)
Expedia
5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.
Bedrooms:
7
Bathrooms:
5
Sleeps:
12
Mediterranean-Style Paradise Retreat in Key Colony Beach Escape to luxury at this stunning Mediterranean-style waterfron ...
From $1270 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Moon Bay, a piece of paradise! It is located on Blackwater Sound in Key Largo, Florida. Unit A210 is an end ...
From $354 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Duval Street Suites full kitchen Old Town with heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $561 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Oceanside Kawama Villa R5
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Come experience ultimate relaxation and comfort in this stunning three-story vacation home. On the first floor, you will ...
From $569 per night (USD)
VRBO
From $3199 per night (USD)
Expedia
BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
Bedrooms:
8
Bathrooms:
9
Sleeps:
20
A Castle on an Island On A Privately Owned Key West Island Private Bridge for Cars and Trucks connected to Key West Fr ...
From $3199 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Relax in Paradise! Enjoy a tropical lifestyle.
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Impeccable 42' Luxury RV: One bedroom, loft with 3 beds,1 Bath stylish kitchen and living areas. Welcoming and spacious ...
From $233 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Luxurious waterfront home with panoramic views, pool, spa, & dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Plein Air Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $852 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to the Keys Life Cottage! This coastal inspired two-bedroom, one-bath home is tucked away on a large landscaped ...
From $172 per night (USD)
VRBO
From $666 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $666 per night (USD)
Expedia

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