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Florida Keys Rentals

From $611 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 $611 per night (USD)
VRBO
From $549 per night (USD)
Expedia
P45 - Spacious 5 bedroom, 4 bath home with spectac
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This spacious 5 bedroom, 4 bath home boasts spectacular open water views, abundant outdoor living space and a peaceful l ...
From $549 per night (USD)
Expedia
From $287 per night (USD)
VRBO
RITA'S PARADISE 37.5' DOCK-ICE MAKER-Cabana Club-TIKI HUT-Screen Porch-Bait Frez
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Perfect home for a Family Gathering, or Extended Family Get Together. Snowbirds welcomed at request dates R ...
From $287 per night (USD)
VRBO
From $725 per night (USD)
VRBO
Perfect Seaside Escape! 3 Relaxing Units w/ Kitchen | Pool + Private Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $725 per night (USD)
VRBO
From $688 per night (USD)
VRBO
Beautiful Sight in Your 3 Ocean View Units, Outdoor Heated Pool, Full Kitchen!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $688 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Paradise Awaits! Spacious Suite w/ Fantastic View
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $202 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Deja Blue Suite [Ocean Pointe 1409]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy coastal comfort at our oceanfront property nestled on 60 lush acres, part of a protected mangrove forest, entered ...
From $300 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
*ALL NEW AND A PERFECT LOCATION! * NEVER RENTED BEFORE!*35' Seawall *Magnificent newly renovated 2 bedroom 1 bath waterf ...
From $354 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nice quiet landing a few blocks from the action on Duval Street. This is a Saturday-Saturday weekly home for the rest of ...
From $202 per night (USD)
VRBO
Click For Pricing
Expedia
Sea Glass Beach Bungalow in Key Colony Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Sea Glass Beach Bungalow! What made us first fall in love with the Florida Keys was the captivating blue/gree ...
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Expedia
From $256 per night (USD)
VRBO
Your Home Base in Key Largo - Close to It All with Beautiful Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the serene scenery, at our charming oceanfront condo at Ocean Pointe Suites. Ideal for couples, solo & budget ...
From $256 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Canal-front, dog-friendly home with heated pool, seawall dock & grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Manatee Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $151 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Gated Community Townhome with Private Beach, Pool, and Tennis Courts!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Save up to 25% on all booking this year! Take your dream Keys vacation in this spacious 2bd/3bth waterfront town home i ...
From $204 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Canal-front, dog-friendly duplex with private heated pool, dock & grills
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Lobster Lodge and Manatee Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $386 per night (USD)
Expedia
From $288 per night (USD)
VRBO
GOLF VILLA - Monthly Rental - 2BD/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $288 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Paradise Getaway Flamingo Island, Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you want to experience the true meaning of a Florida Keys Island Vacation then look no further than our spacious and ...
From $378 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Peacock Shores Islamorada - Vacation On The Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy ...
From $461 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Beachfront townhome. Steps to the beach, dock, pool, and tennis w/pickle ball.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Long Key Beach has been rated top 10 winter beaches by Yahoo travel and one of the best beaches rated by the Sun Sentine ...
From $209 per night (USD)
VRBO
From $282 per night (USD)
Expedia
R & K's Marathon Paradise 2/2 Duplex w/35` Dock &
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
VACA-21-501R & K's Marathon Paradise w/ Cabana Club Included7 Day Minimum RentalSaturday to Saturday booking onlyunless ...
From $282 per night (USD)
Expedia
From $519 per night (USD)
VRBO
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + 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! Looking to ma ...
From $519 per night (USD)
VRBO
From $688 per night (USD)
VRBO
Excellent Choice! 3 Spacious Units, Heated Pool, Full Kitchen, Ocean View!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $688 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Breeze at 1800 Atlantic — Your Luxurious Oceanfront Escape in Key West Discover the ultimate blend of co ...
From $376 per night (USD)
VRBO
From $585 per night (USD)
Expedia
P98 - 4 bed, 4 bath home with dockage and private
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention given to ea ...
From $585 per night (USD)
Expedia
From $320 per night (USD)
VRBO
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Marathon the heart of the Florida Keys! Here in Marathon we have several restaurants within minutes, Sombrero ...
From $320 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We would like to cordially invite you to our vacation home, Sangria Sunrise! SangriaSunriseVacations@gmail. com Our co ...
From $324 per night (USD)
Expedia
From $371 per night (USD)
VRBO
P77 - Sombrero Beach - Pool home offering 3 bedroo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This updated 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 min ...
From $371 per night (USD)
VRBO
From $513 per night (USD)
Expedia
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $513 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Coastal Charm: 2BR Condo, Patio, Pool Views, Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Coastal Charm, your serene seaside retreat located in Marathon, Florida! This charming condo offers 2 bedroom ...
From $237 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Bird of Paradise: 3BR Condo, Atlantic Views, Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and t ...
From $346 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Top Floor Condo w/ Ocean Views Near Pool [Ocean Pointe 3405]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy sunrise and endless ocean views from the balcony of our top floor suite located in the 3rd building at Ocean Point ...
From $318 per night (USD)
VRBO
From $665 per night (USD)
Expedia
Caribbean Sunsets: 3BR Home Gulf Views Pool & Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Property Overview: Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breat ...
From $665 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Sea Ray Cove; Pool, 75’ Dock and steps to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2025- New concrete dock, fenders and fish filet table. This ground level waterfront home has received a new face lift. ...
From $470 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Tropical: 4BR Luxury Home Gulf Views Pool and Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom ...
From $516 per night (USD)
Expedia
From $859 per night (USD)
VRBO
Casa Rosa: 4BR/4BA house, pool, near Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $859 per night (USD)
VRBO
From $205 per night (USD)
VRBO
NAUTI HIDEAWAY - 2/2, Slip, Ramp, Pool, Trailer Parking, Bait Freezer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
7 DAY MINIMUM RENTAL - No Nightly Rentals - NO EXCEPTIONS per law. MAXIMUM OCCUPANY is 4 persons – This includes infan ...
From $205 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Reel Paradise 2 in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautifully remodeled two-bedroom, two-bath half-duplex offers brand new everythingincluding a sparkling new pool! ...
From $338 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Million Dollar View in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Why go to the Caribbean when you can find Paradise right here in the Heart of the Keys. Spectacular, direct, unobstructe ...
From $336 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Torchview Lookout – Your Private Waterfront Retreat! Escape to paradise at Torchview Lookout, a secluded 3-b ...
From $485 per night (USD)
Expedia
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VRBO
Easy access to the Ocean and Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Leave your worries and enjoy the island life style. I promise you that this will be your favorite gateway. Beautiful san ...
Click For Pricing
VRBO
From $1165 per night (USD)
Expedia
**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $1165 per night (USD)
Expedia
From $323 per night (USD)
VRBO
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You have many ...
From $323 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Copacabana, Overlooking the Gulf!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the Gulf of Mexico allows for the great views at this beautiful home. Bring your boat or rent one! The new d ...
From $508 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Tranquilo Paraiso [Ocean Pointe 2407]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come unwind at our tastefully decorated, 2 bedroom, 2 bathroom condo located on the top floor of Building 2 at Ocean Poi ...
From $304 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Island Dreaming in the Heart of Tavernier - Pool, Pickleball & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical Oceanfront Escape in the Upper Keys – 2BR/2BA Condo at Ocean Pointe Unwind in island comfort with sweeping oce ...
From $327 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Classic Key West living w/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $487 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This lovely oceanfront home is at Mile Marker 85 in exclusive An ...
From $433 per night (USD)
Expedia
From $417 per night (USD)
VRBO
New Construction home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $417 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $362 per night (USD)
Expedia
From $386 per night (USD)
VRBO
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $386 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Convenient central Marathon location, canal view.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cute and super clean! One bedroom and one bath, nicely decorated & furnished. Bedroom has queen bed with topper. Bedroom ...
From $150 per night (USD)
Expedia
From $349 per night (USD)
VRBO
🌇 Ocean Sunset Views with Pool and Dock 🌇
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful s ...
From $349 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Paradise Found
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Gorgeous canal front property located in Duck Key. This fabulous home has 3 bedrooms 3 baths and garage. Sleeps 8 person ...
From $476 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!$
From $381 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $381 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Sunbeam Dream Oasis [Ocean Pointe 4211]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunbeam Dream is a coastal inspired two bedroom two bathroom apartment in Building 4 at Ocean Pointe. Tastefully decorat ...
From $378 per night (USD)
Expedia
From $295 per night (USD)
VRBO
FALL '25 Deals! OCEANFRONT Lux 1350sf w/ Stunning Views & All Amenities of home!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Rates for remaining Fall '25 dates have just been reduced for quick sell-off! Why not treat yourself and get away for ...
From $295 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Dog-Friendly Gulf-Front Home w/ Private Pool/Dock, Fast WiFi, and Washer/Dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Marathon Memories Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $233 per night (USD)
Expedia
From $386 per night (USD)
VRBO
OCEANFRONT CONDO w/Lake, 2Kayaks, 2Paddleboards, 2Bikes, Tennis, Boat Ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACK ...
From $386 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Blue Paradise 5bed/5bath walking distance to the b
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Welcome to Blue Paradise: Your Dream Getaway in the Heart of Sombrero!Escape to luxury and comfort in this stunning new ...
From $435 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to paradise! The Silly Sailfish is 1 of 8 stand alone single family homes within the 25 unit community and very ...
From $559 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Tavernier Escape! Waterfront Vibes, Sand, Sun & Pure Keys Magic.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to our stunning 2-bedroom condo in the heart of Tavernier, where the beauty of the Florida Keys awaits. Nestled j ...
From $291 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Poolside townhouse in Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Ke ...
From $231 per night (USD)
VRBO
Click For Pricing
Expedia
Ocean side on canal with easy access for boaters
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 BDRM, 2BTH. Master bdrm has a king bed and full bathroom inside the master. 2nd room is spacious with two full beds. ...
Click For Pricing
Expedia
From $542 per night (USD)
VRBO
Newly renovated coastal home; Marina, Pools, Lagoon, Bikes, Tiki’s and More!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your Florida Keys vacation in this upgraded modern coastal home that is waterfront to a saltwater lagoon. Boater's ...
From $542 per night (USD)
VRBO
From $252 per night (USD)
Expedia
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great location on a deep water lagoon in the heart of Marathon. Uniquely situated in the heart of Marathon, Unit A or ...
From $252 per night (USD)
Expedia
From $1066 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1066 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Dolfan Oceanfront Cottage Direct oceanfront with 5
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vaca-21-243This beautiful and spacious home has Direct Oceanfront Living. Ocean views and deep water dockage with boatin ...
From $700 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Heart of Marathon with Gulf and Ocean access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Uniquely situated in the heart of Marathon, Unit B or 9922 is a 2 bedroom, 2 bath separate private home/villa/bungalow w ...
From $246 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Turquoise Lagoon LLC, wide open turquoise views of the lagoon
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Great view of the lagoon/bay right from the living room and out on the porch. Watch dolphins and manatees and fish jump. ...
From $279 per night (USD)
Expedia
From $776 per night (USD)
VRBO
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $776 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Beautiful Waterfront Vacation home to enjoy the Florida Keys in Style
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Comfortable and spacious Key Largo home welcomes up to eight guests comfortably but can sleep 10 . Enjoy a getaway in P ...
From $570 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Waterfront home with ocean views, dock, & private outdoor pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Sombrero Beach Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $473 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Pure Aquamarine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $179 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Enjoy the Florida Keys like a local with this Private Waterfront Home with Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come enjoy the Florida Keys like a local with a Private Tropical Waterfront Home with over 60 Feet of Deep Water Concret ...
From $423 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, ...
From $433 per night (USD)
Expedia
From $603 per night (USD)
VRBO
123 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
If you are looking for the hottest spot in Key Largo, then look no more. The first impression of 123 Mariners Club is qu ...
From $603 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Stunning Views- Ocean Pointe Building 5 King Suite + Pool, Beach & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your ultimate vacation getaway in the sun-soaked Florida Keys! This stunning 2 bedroom, 2 bathroom condo at O ...
From $304 per night (USD)
Expedia
From $349 per night (USD)
VRBO
CASA NAUTICA @KEY COLONY BEACH🌴OPEN DEC’25🌴CABANA CLUB WITH PRIVATE BEACH & POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to CASA NAUTICA-KCB, where paradise awaits you with a beautiful 2 bedroom, 2 bath cottage style retreat with exc ...
From $349 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Florida Keys Chic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 ...
From $204 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Waterfront Oasis w/ Pool, Tiki Lounge, Dock & BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover your dream vacation in this freshly remodeled 3-bedroom, 2-bath gem on a stunning flow-through canal with direc ...
From $415 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Canal front with Pool & 50 feet of Dock on each side / Cabana Club Included!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DUPLEX, THIS LISTING NUMBER IS 1275459 OTHER SIDE LISTING IS 561552. EACH SIDE HAS 4 BEDROOMS 3 BATHS, YOUR OWN POOL AND ...
From $506 per night (USD)
Expedia
From $2090 per night (USD)
VRBO
Sublimely private luxury home with enveloping oceanfront views near Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxury Villa of the Setting Sun -Near Key West Fl Our calendar is updated in real-time & our nightly rates are accurate ...
From $2090 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Casita Key Largo Getaway.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
WELCOME TO FLORIDA 🌺 KEYS LIVING! Enjoy your stay at Casita Key Largo in a beautifully decorated 2019 mobile home in ...
From $222 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Waterfront Home in Islamorada with outdoor kitchen, pool, spa, boat dockage
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Tut’s Cay located in Islamorada in the Florida Keys. Our home is centrally located in our favorite part of th ...
From $432 per night (USD)
VRBO
From $335 per night (USD)
Expedia
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Mango Tree Cottage – Old Town Key West Gem! Location, Location, LOCATION! Welcome to The Mango Tree Cottage, your ...
From $335 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Beachside @ Torchview Waterfront Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Beachside at Torchview Located on the serene shores of Big Torch Key in the Florida Keys Beachside at Torchv ...
From $398 per night (USD)
VRBO
From $457 per night (USD)
Expedia
A PEACE OF PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $457 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Venetian Shores Islamorada New Home w/dock & pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Located in Venetian Shores, Islamorada Luxurious bayside waterfront home on a wide canal with easy access to the ocean ...
From $881 per night (USD)
VRBO
From $797 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $797 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Peace and tranquility on this lakefront pool home in Buccaneer Point, Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private house with a pool on the lake in Buccaneer Point, Key Largo. Very quiet neighborhood on a closed lake. 3 bedroo ...
From $372 per night (USD)
VRBO
From $313 per night (USD)
Expedia
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $313 per night (USD)
Expedia
From $363 per night (USD)
VRBO
FALL Discounts-Blue Ocean Bungalow 3bdr./3ba. updated canal access Sombrero
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water can ...
From $363 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Blue Breeze: 3 BR, 2.5 BA House in Grassy Key, Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled within the tranquil Grassy Key neighborhood, Blue Breeze offers an idyllic escape. This spacious 3-bedroom resid ...
From $321 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Marathon
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Resort condo in Marathon. On site tiki bar/grill, live music, kids activities, beautiful pool and outdoor grills. Rent w ...
Click For Pricing
VRBO
From $329 per night (USD)
Expedia
Canal side location with beach & pool club membership!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 2 Bedroom/2 Bath Duplex is perfect for your vacation in paradise or winter getaway! The house can sleep 6. There is ...
From $329 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Enjoy Sunny Skies & Serene Seas from Top Floor End Unit at Ocean Pointe Bldg 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Kick back and relax from this top floor, oceanfront, condo in building 2 at Ocean Pointe Suites Key Largo. Ideal for Fa ...
From $311 per night (USD)
VRBO
From $832 per night (USD)
Expedia
Waterfront Home, 200ft Dock, Gulf Access, Kayaks, Bicycles, Mini Golf, Game Room
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
WELCOME TO SOL MATE VACATION HOME - MARATHON, FLORIDA KEYS Welcome to Sol Mate Vacation Home, your private waterfront r ...
From $832 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Gorgeous oceanfront retreat with marina, pool, & ocean views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Vitamin Sea - Ocean Pointe #3412 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $235 per night (USD)
VRBO
From $491 per night (USD)
Expedia
802 Mariners Club Key Largo | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Take a deep breath…enter…and exhale…you have arrived. A bright and immaculately clean home, 802 Mariner’s Club is the pe ...
From $491 per night (USD)
Expedia

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