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From $2598 per night (USD)
VRBO
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. Best of all, when you ...
From $2598 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Curry House Room 1 - Near Duval, Pool & Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $351 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Sunrise Breeze on the Marina [Ocean Pointe 5302]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Breeze located on the 3rd floor of the 5th bldg, a premier location at Ocean Pointe. Our sp ...
From $327 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Tiny home in Key Largo with Private Dock, Tiki Hut and Boat Lift
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Peaceful, quiet and private gated/waterfront community at the tip of the Florida Keys (Mile Marker 112) in Manatee Cove. ...
From $377 per night (USD)
Expedia
From $1621 per night (USD)
VRBO
4BR Key Largo Stay – Pool, Parking + Beach Club
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Endless Summer #42 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of pea ...
From $1621 per night (USD)
VRBO
From $1621 per night (USD)
Expedia
4BR Key Largo Villa w/ Beach & Marriott Perks
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Gull's Nest #36 Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean ...
From $1621 per night (USD)
Expedia
From $1283 per night (USD)
VRBO
Luxury Villa by the Ocean | Pool & Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Tranquility #19 (3 Bed / 2.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace ...
From $1283 per night (USD)
VRBO
From $1283 per night (USD)
Expedia
Key Largo 3BR Villa | Pool, Kayaks & Resort Perks
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Hideaway #23 (3 Bed / 2.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1283 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Super Comfy and modern with the extras!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom, 2 bathroom large house with game room, tall ceilings, lots of entertaining space and great dock. Comfy couch, ...
From $487 per night (USD)
VRBO
From $603 per night (USD)
Expedia
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)
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 $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 $459 per night (USD)
VRBO
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)
VRBO
From $416 per night (USD)
Expedia
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)
Expedia
From $581 per night (USD)
VRBO
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)
VRBO
From $255 per night (USD)
Expedia
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)
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 $254 per night (USD)
VRBO
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)
VRBO
From $171 per night (USD)
Expedia
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)
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 $402 per night (USD)
Expedia
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)
Expedia
From $236 per night (USD)
VRBO
*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)
VRBO
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)
VRBO
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)
VRBO
From $227 per night (USD)
Expedia
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)
Expedia
From $299 per night (USD)
VRBO
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)
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 $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)
VRBO
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)
VRBO
From $563 per night (USD)
Expedia
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)
Expedia
From $387 per night (USD)
VRBO
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)
VRBO
From $196 per night (USD)
Expedia
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)
Expedia
From $339 per night (USD)
VRBO
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)
VRBO
From $483 per night (USD)
Expedia
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)
Expedia
From $720 per night (USD)
VRBO
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)
VRBO
From $234 per night (USD)
Expedia
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)
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
From $304 per night (USD)
VRBO
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)
VRBO
From $304 per night (USD)
Expedia
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)
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

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