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From $603 per night (USD)
VRBO
Gorgeous Beachfront Home with a pool. Water views from every direction.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Step into your own island paradise! Welcome to this 5 bedroom 3 bath home. Featuring a large private beach with a heated ...
From $603 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Paradise in Key Largo, FL
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy your vacation in this brand new recreational vehicle with great taste in interior design. This unit has an extende ...
From $293 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Private Parking, Heated Pool - Sweet Caroline
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $613 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Private Parking , Heated Pool - Key Lime Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $338 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Heated Pool, Epic Location - Sugar Pie Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $338 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Heated Pool, Epic Location - Honeybun Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $348 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Private Parking, Heated Pool - Banana Split
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $395 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Private Parking, Heated Pool - Creme Brulee Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $333 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Marina & Ocean Front Suite 5202
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your family will be close to everything when you stay at this centrally-lIdeal for couples, solo & budget trav ...
From $329 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Tavernier Keys Home w/ 70’ Dock & 20k Boat Lift on Bayside! 3/2.5 Plus Game Room
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gorgeous and Spacious Bayside Tavernier Keys Home with a 70’ foot Dock for your Boat and 20,000 lb Boat Lift. Be in the ...
From $394 per night (USD)
Expedia
$Islamorada Anglers Reef! “Sandbar Bungalow Villa\ AMAZING! Middle row location!$
From $489 per night (USD)
VRBO
Islamorada Anglers Reef! “Sandbar Bungalow Villa\" AMAZING! Middle row location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AMAZING MIDDLE ROW! COMPLETELY UPDATED! BOAT SLIP AVAILABLE This oceanfront resort is a boutique complex of 52 homes ins ...
From $489 per night (USD)
VRBO
From $720 per night (USD)
Expedia
Bay Front Home With Magnificent Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Located in Islamorada, the fishing capital of the world, this house is tucked away in a quite neighborhood on the bay si ...
From $720 per night (USD)
Expedia
From $270 per night (USD)
VRBO
COLORFUL COCKTAIL @ Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect Key West getaway! Nestled in the coveted Shipyard community of Truman Annex, this beautifully ma ...
From $270 per night (USD)
VRBO
From $377 per night (USD)
Expedia
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa + Last Key White Glove Service
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! When explorin ...
From $377 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ocean front condo. Nothing but water views from every room! NO other structures but Channel 5 bridge in sight. Access to ...
From $337 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Sombrero Beach Home - Heated Pool, Kayaks, Private Road
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Renovated 3 bedroom, 2.5 bath home just a block to beautiful Sombrero Beach in Marathon – a rare soft sand beach in the ...
From $667 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Home Away from Home Pet Friendly - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $479 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Balcony Dining Space & Roof Top Deck- Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $586 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Budget Friendly, Couples Welcome - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $479 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Roof Top Deck, Sleeps 6 w/3 Kings - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $586 per night (USD)
Expedia
From $357 per night (USD)
VRBO
A Palm Oasis at Mills Place in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming two bedroom, two and one half bath townhome has recently been updated and added to our rental program! Fre ...
From $357 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Coastal Inspired Cottage in Bahama Village Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $274 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths ...
From $412 per night (USD)
VRBO
From $403 per night (USD)
Expedia
Tree Top Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
On 7/6/24 I have bought a new oven, microwave, dishwasher, washer and dryer and barbeque to make your vacation very com ...
From $403 per night (USD)
Expedia
From $334 per night (USD)
VRBO
MONTHLY RENTAL, 1 block to Duval, POOL, personal resort, 3/3, pets OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $334 per night (USD)
VRBO
From $182 per night (USD)
Expedia
March Availability, Beach, 70 ft Dock - Marathon VACA-23-16 Entire House
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 bedroom/3 bath home, 2 of which are master bedrooms. All mattress with memory foam. Four 55" 4K TV's with Direct TV ...
From $182 per night (USD)
Expedia
From $403 per night (USD)
VRBO
SC1-Southern Comfort One at 310 11th St. In KCB. Private Pool & BEST Backyard.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Southern Comfort One (SC1) – Your Private Key Colony Beach Escape. Address: 310 11th St. Key Colony Beach, F ...
From $403 per night (USD)
VRBO
From $636 per night (USD)
Expedia
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $636 per night (USD)
Expedia
Click For Pricing
VRBO
Spring Break in the Sun! Islamorada townhome w/ beach, pool in gated community!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just reduced for last minute Spring Break family!! Enjoy Townhome in the heart of the Florida Keys, under 1.5 hours fro ...
Click For Pricing
VRBO
From $367 per night (USD)
Expedia
**CASITA OLIVIETTA @ SOLARES HILL** Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $367 per night (USD)
Expedia
From $851 per night (USD)
VRBO
Island pool home awaits in Islamorada's Port Antigua
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, til ...
From $851 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There is no better place for a Florida Keys Getaway than the beautiful Ocean Pointe Suites of Tavernier. Located between ...
From $353 per night (USD)
Expedia
From $861 per night (USD)
VRBO
4BR Waterfront Home w. Pool, Dock, Game Room & short walk to Sombrero Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This home is professionally managed by Rentals in Paradise, a local company in Marathon. Upon entering our driveway, yo ...
From $861 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Relax amongst the tropical sights and sounds in this charming ocean front condo. Ideal for couples, solo & bud ...
From $342 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Stary Net - Ocean Waterfront 3BR 3BA Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Key Largo and the Florida Keys... an unhurried, unspoiled natural paradise offering spectacular sunsets, gentle breezes ...
From $212 per night (USD)
VRBO
From $1457 per night (USD)
Expedia
Springtide House at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Discover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community!! ...
From $1457 per night (USD)
Expedia
From $1845 per night (USD)
VRBO
Suncoast House at Lunara Bay
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Summary: Discover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community! Su ...
From $1845 per night (USD)
VRBO
From $1422 per night (USD)
Expedia
Aquaria House at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Experience the Aquaria House at Lunara Bay - a collection of 26 luxury homes in a gated community! This stunni ...
From $1422 per night (USD)
Expedia
From $1457 per night (USD)
VRBO
Capmar House at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Capmar House is a beautiful waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes ...
From $1457 per night (USD)
VRBO
From $1581 per night (USD)
Expedia
Mirador House at Lunara Bay
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Summary: Mirador House is a gorgeous waterfront 5-bedroom, 5.5-bath home at Lunara Bay - a collection of 26 luxury home ...
From $1581 per night (USD)
Expedia
From $1457 per night (USD)
VRBO
Evershore Estate at Lunara Bay | Wellness Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Evershore Estate is a waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a g ...
From $1457 per night (USD)
VRBO
From $1419 per night (USD)
Expedia
The Seagate Estate at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Sea ...
From $1419 per night (USD)
Expedia
From $1436 per night (USD)
VRBO
Spindrift House at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Spindrift House is a beautiful waterfront 4-bedroom, 4-bath home at Lunara Bay—a collection of 26 luxury homes ...
From $1436 per night (USD)
VRBO
From $1457 per night (USD)
Expedia
Waterlane House at Lunara Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Waterlane House is an inviting waterfront 4-bedroom, 4.5-bath home at Lunara Bay - a collection of 26 luxury h ...
From $1457 per night (USD)
Expedia
From $1423 per night (USD)
VRBO
Mastway House at Lunara Bay - Wellness Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Mastway House is a waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a gate ...
From $1423 per night (USD)
VRBO
From $459 per night (USD)
Expedia
44ft Seawall at Sportsman's Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
44ft Seawall at Sportsman's Paradise True Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba ...
From $459 per night (USD)
Expedia
From $416 per night (USD)
VRBO
2 BED/2BATH OCEAN FRONT CANAL -- BRING YOUR BOAT OR RENT ONE!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you've never heard of or been to what locals have classified as "The Gem of the Florida Keys," Key Colony Beach in Ma ...
From $416 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Mariner's Club 806 • Spacious 4/3 • 8 Beds • Pools & Resort Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Sea La Vie — Unit 806, your Key Largo escape in the heart of Mariner’s Club, one of Key Largo’s most sought- ...
From $581 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Glistening, waterfront home, Private pool, 45' Dock & Cabana Club with beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
HOUSE: Modern-contemporary décor with comfort throughout the house and patio. PRIVATE PATIO: Relax in the 8 x 12, salt- ...
From $255 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Island Time On the Green at Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Time on the Green - This is a beautiful, intimate two-story open plan townhome backing to one of two community po ...
From $359 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Ocean front with private beach and pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this ocean front piece of paradise and relax from the daily stress. This spacious two bedrooms two bathrooms apart ...
From $367 per night (USD)
VRBO
From $431 per night (USD)
Expedia
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $431 per night (USD)
Expedia
$\Casa Azul Villa\- Stunning Ocean Views, Keys-Marathon FL$
From $812 per night (USD)
VRBO
\"Casa Azul Villa\"- Stunning Ocean Views, Keys-Marathon FL
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Large open living area, kitchen, and dining. Sail out for the best fishing in the world. Marathon is known for its beac ...
From $812 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Yellowtail Getaway 3 bedrooms,4 beds,3 bath,boat dock,ice maker and heated pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful remodeled house 3 bedrooms, 3 bath in the heart of Marathon Key. Located on a flow-through canal you will enjo ...
From $371 per night (USD)
Expedia
From $2285 per night (USD)
VRBO
House and guest house with Boat dock, sunsets, jacuzzi, pool, slide, tiki, etc
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Truly need to look at pictures, but this property is private and of a KIND, on the water and room to dock 2-3 boats; has ...
From $2285 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Tastefully Remodeled Island Villa in Key Largo, 2 Bedrooms, 2 Bathrooms.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Luxury Villa in Private Resort Community of Port Largo. Spacious 2 bedrooms, 2 bathrooms, 1600 sq./ft.(149sq./meters). C ...
From $254 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Smith Families Southernmost 2 Bedroom retreat, Key West style beach vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $171 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $408 per night (USD)
Expedia
From $609 per night (USD)
VRBO
P59 - 4 bed, 4 bath home with dockage and private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Fresh and fabulous best describe this addition to our gorgeous gulf side community! This 4 bedroom, 4.5 bathroom home ...
From $609 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Key Lime Cottage - Your Duck Key Retreat! Nestled on the picturesque Duck Key, just outside of Marathon, ...
From $406 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Key Largo Paradise-Neighbors to the Dolphins
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Little Paradise, your home away from home. Enjoy a private home with amazing location. This home is loca ...
From $262 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Hyatt Beach House! Quiet Key West Location! Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $602 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $402 per night (USD)
VRBO
From $236 per night (USD)
Expedia
*Snowbirds Paradise*
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Lovey 1/1 waterfront home up on stiles with parking for 2 vehicles. my favorite is the 32ft patio with Amazing breath ...
From $236 per night (USD)
Expedia
From $592 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $592 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Canal front, dockage, 2 bedroom, 2 bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open water views from this 2 bedroom, 2 bath stand alone home, 35 foot seawall for docking your boat. Contemporary desig ...
From $339 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Dates available Oct, Nov, Dec 2023
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Flor ...
From $227 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Tailgate Key at the Key West Golf Club in key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $299 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Keys Waterfront Condo: Beach, Pool & Sunset Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Come enjoy our oceanfront condo at Ocean Pointe Suites in Tavernier, Florida! You'll have direct access to the ...
From $301 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
Sweet's Spot at The Truman Annex in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $1067 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Keys Tropical Bungalow! delightful and spacious 3/2 makes a great getaway.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Tropical Bungalow! This lovingly maintained, delightful and spacious 3/2 with large expanded porch makes a great ...
From $217 per night (USD)
VRBO
From $493 per night (USD)
Expedia
2402 Ocean Pointe - 2 bedroom condo upgraded with clean lines and coastal colors
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Complete renovation inspired by the homeowner's love of clean lines and cool, coastal colors. From the moment you enter ...
From $493 per night (USD)
Expedia
From $580 per night (USD)
VRBO
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this bea ...
From $580 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Red 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 b ...
From $289 per night (USD)
Expedia
From $657 per night (USD)
VRBO
Canal Front with Dock, Private Pool, Huge Tiki Hut w/ TV, Bikes, Paddleboards!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki ...
From $657 per night (USD)
VRBO
From $1711 per night (USD)
Expedia
Oceanfront 2 Homes | Private Beach & Pool | 3 Acre
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Oasis4rent! Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully ...
From $1711 per night (USD)
Expedia
From $974 per night (USD)
VRBO
Luxury Holiday Vaca Here! Large outdoor space and dock. Lg hot tub and pool!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
NEW-“2 homes in 1”- PRIVATE-WATERFRONT HOME -only a 5 minute walk to the beach Located on a large, deep canal and is ...
From $974 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Best Time at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $211 per night (USD)
Expedia
From $425 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $425 per night (USD)
VRBO
From $744 per night (USD)
Expedia
The Lazy Lime – Spacious 5BR Retreat with Pool, Hot Tub & Open Water Views
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The Lazy Lime is a stunning gulf front newly updated 5 bedroom 3 bathroom single family home. Ask about adding the garde ...
From $744 per night (USD)
Expedia
From $457 per night (USD)
VRBO
**TURTLE COVE VIEWS** Cottage/ Boat Slip/ Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TURTLE COVE V ...
From $457 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Poolside Hangover at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...
From $220 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Bayside Sunsets
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
https://vimeo.com/reviews/7059076e-bcee-4484-bd14-e03276c26683/videos/1193830235 Check out the v ...
From $364 per night (USD)
VRBO
From $331 per night (USD)
Expedia
A Duck on the Green at the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $331 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Amazing Location! Relaxing Room, Free Breakfast, Outdoor Pool w/ Fantastic View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, standard ...
From $162 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Wow!!! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Ocean Front Tiki Bar!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This updated 3 bedroom, 2 bath home with private canal lot is located in the heart of The Florida Keys in Marathon at Mi ...
From $293 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Southernmost Sanctuary at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $563 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Islamorada's Anglers Reef - Vaca in Style
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 128 Anglers Way: "Morada Daydreaming". Our home away from home in the Angler's Reef exclusive gated community ...
From $387 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 Atlantic Experience comfort and elegance in this beautifully reno ...
From $196 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Yellowtail Island Retreat - 3BR Keys Home w/ Pool, Dockage, Porch & Canal Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
$300 DISCOUNT FOR WEEK OF MAY 16TH, 2026 Roof is being redone (it may take up to 1 or 2 days) Welcome to Yellowtail Is ...
From $339 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Majestic Marina View- 2/2.5 townhome looking over Hawks Cay Marina.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience island serenity and unbeatable waterfront views from this beautifully situated Duck Key villa. Sip a cocktail ...
From $483 per night (USD)
VRBO
From $720 per night (USD)
Expedia
Amazing Key Largo Tropical Paradise 3/3 Townhouse with Water Lagoon view
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful 3 bedroom 3 bath townhome overlooking a tranquil lagoon. Swim or Snorkel the Saltwater Lagoon, relax in the p ...
From $720 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $234 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Where the sea, sun, and sand are just outside your door!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come on in and enjoy your worry-free vacation. This unit has all the comforts of home. Just bring your bathing suit and ...
From $336 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Very Nice 3 Bedroom Home With Large Lot! Built to entertain! Boat Ramp!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This is a beautiful property that offers a home like atmosphere as well as complete privacy. The property is in the comm ...
From $126 per night (USD)
VRBO
From $403 per night (USD)
Expedia
ALL DOCKED OUT~ Key Colony Retreat Sandy beach's and sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This elegantly furnished 2 bedroom waterfront retreat is located in beautiful Key Colony Beach. This community is one o ...
From $403 per night (USD)
Expedia
From $192 per night (USD)
VRBO
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom 2 bath stilt home with large screened in porch overlooking canal and lush tropical coconut palms. Boat dock Wi ...
From $192 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Spectacular Key Largo Sunsets - 2 bedroom Townhouse sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience paradise in this Bayside "Sunset Side" townhouse in the Florida Keys. Nestled in a private gated community on ...
From $276 per night (USD)
Expedia
From $1069 per night (USD)
VRBO
Oversized home for the whole family w/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1069 per night (USD)
VRBO
From $337 per night (USD)
Expedia
High Tide at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $337 per night (USD)
Expedia

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