Florida Keys National Marine Sanctuary Rentals
- From $1025 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $1025 per night (USD)VRBO
- From $480 per night (USD)
VRBO
The Key West Bougain Villa, a Monthly Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Ke ...
From $480 per night (USD)VRBO
- From $407 per night (USD)
VRBO
~FISH CAMP!~ Family friendly, canal front, monthly rental.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $407 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Waterfront Home w\/ Private Dock, Outdoor Shower & Home Office - Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Casa Palmera Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $341 per night (USD)Expedia
- Click For Pricing
VRBO
Pirates Pleasure Fishing and Snorkeling.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property ...
Click For PricingVRBO
- From $756 per night (USD)
Expedia
Waterfront luxury Villa (51) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $756 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful 2\/2 Florida keys home rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with privat ...
Click For PricingVRBO
- From $370 per night (USD)
Expedia
La Casita
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, fully furnished 2BD/2BA single family home is located in the prestigious Casa Marina neighborhood. Speci ...
From $370 per night (USD)Expedia
- From $405 per night (USD)
VRBO
B307 Moon Bay | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
7-night minimum stay requirement. This fully renovated bay front end-unit condo in Moon Bay has been reconfigured to a ...
From $405 per night (USD)VRBO
- From $689 per night (USD)
Expedia
RELAX AWAY- NEW 4BDRM W\/ 40FT DOCK & PRIVATE POOL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
RELAX AWAY @ SOMBRERO - ENJOY OUR NEW 1800 SQ FT HOME, 4/3 WITH COVERED BALCONY & PATIO & SPACIOUS POOL PERFECT FOR YOUR ...
From $689 per night (USD)Expedia
- From $466 per night (USD)
VRBO
Villages at Hawks Cay Villa with Spa
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
In response to COVID-19, our villa will be disinfected and sanitized professionally prior to all check-ins. We offer ni ...
From $466 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Tranquil Top Floor Condo w\/ Ocean Views close to Attractions in the Upper Keys
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Atlantic Ocean greets you in this charming 1 bedroom condo on the top floor of building two, located in Ocean Pointe ...
From $292 per night (USD)Expedia
- From $516 per night (USD)
VRBO
Hidden Paradise: A Serene Waterside Retreat - 3-Bedroom, 3-Bath Single Family
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover comfort and ample space in this three-bedroom waterfront oasis, a perfect single family abode that boasts an ex ...
From $516 per night (USD)VRBO
- From $361 per night (USD)
VRBO
Family Friendly House In Paradise
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 t ...
From $361 per night (USD)VRBO
- From $430 per night (USD)
VRBO
KEY COLONY BEACH REMODELED! 80FT DOCK. CABANA CLUB INCLUDED. 331
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
KEYS BEST SECRET ISLAND. NO NEED TO BE ELSE WHERE.. BEAUTIFUL ISLAND, HAS EVERYTHING YOU NEED TO RELAX. 5 STAR RESTAUR ...
From $430 per night (USD)VRBO
- From $569 per night (USD)
Expedia
124 Mariners Club Key Largo | 2 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ahh...you are here! Villa 124 at Mariners Club is a two bedroom, two and one-half bath luxury villa with stunning harbo ...
From $569 per night (USD)Expedia
- From $487 per night (USD)
VRBO
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $487 per night (USD)VRBO
- From $391 per night (USD)
Expedia
4409 Ocean Pointe Suites | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
No zoom lens required for THIS view! A recently renovated, open concept living area decorated with pops of color and ch ...
From $391 per night (USD)Expedia
- From $502 per night (USD)
VRBO
Marlin House at Mariner's Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in a secluded and quiet lush tropical setting. This is a Two bedroom, two bath 2nd floor condo with gorgeous ma ...
From $502 per night (USD)VRBO
- From $555 per night (USD)
VRBO
OCEANFRONT Private Pool Dock Approved Pet OK! Gated Estate - A Tropical Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Mar Azul is a High-end Oceanfront Residence overlooking the tranquil Offshore Flats of Marathon. Enjoy a Secluded, Luxur ...
From $555 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Parrotfish Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $368 per night (USD)VRBO
- Click For Pricing
Expedia
The Hammocks- Marathon Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful centrally located resort with full amenities. Water sport rentals on site, walking distance to restaurants. Ti ...
Click For PricingExpedia
- From $586 per night (USD)
VRBO
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
It’s time to live the Florida Keys dream! Claim a corner of paradise all for yourself in this 3-story, 3-bedroom, 3-1/2 ...
From $586 per night (USD)VRBO
- Click For Pricing
Expedia
Lovely 1\/1 condo with assigned dock on open canal
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our peaceful and centrally-located condo; in a quiet neighborhood which encourages walking and biking with a boat ...
Click For PricingExpedia
- From $195 per night (USD)
VRBO
Paradise in Plantation Key\/Deep Water Canal House\/Boat Dock\/MM 89
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! ...
From $195 per night (USD)VRBO
- From $1863 per night (USD)
VRBO
Lush Garden Estate in Islamorada FL, W\/ Pool, Dockage, Ocean Front & great views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on t ...
From $1863 per night (USD)VRBO
- From $549 per night (USD)
VRBO
REOPEN NOV 23-30, 2024\/~POOL HEAT\/LG ICE MACHINE, DOCK~BOOK NOW~INSTANT BOOK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Upon entering the driveway to VRBO's Premiere Partner's home, SUNNY DAZE ESCAPE you will know why we are a premiere priv ...
From $549 per night (USD)VRBO
- From $530 per night (USD)
Expedia
Oceanfront Balcony w\/Panoramic View, Beach, Pool, Hot Tub, Tennis & Fishing Pier
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Get that peaceful "Keys-y" feeling... Upon entering our luxuriously remodeled condo, you will be impressed with expansiv ...
From $530 per night (USD)Expedia
- From $452 per night (USD)
VRBO
Beachfront Hideaway in the heart of Key Largo! Your own private beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“Treetops” is a truly unique slice of paradise. Nestled amid the trees, with a peekaboo view of the Gulf of Mexico, and ...
From $452 per night (USD)VRBO
- From $212 per night (USD)
Expedia
Your Best Fishing And Relaxing Experience! (2\/2) Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This secluded waterfront home is located on a cul-de-sac quiet street mile marker 25. This home has all the amenities yo ...
From $212 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** Florida Keys, Big Pine Key, located in Big Pine Key Florid ...
From $331 per night (USD)VRBO
- From $238 per night (USD)
Expedia
Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $238 per night (USD)Expedia
- From $265 per night (USD)
VRBO
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
water front home is located on 100 foot wide canal with your own 30 feet of Free dockage. We are pet friendly. Furnished ...
From $265 per night (USD)VRBO
- From $771 per night (USD)
Expedia
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $771 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $180 per night (USD)VRBO
- From $601 per night (USD)
Expedia
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Palma, Live the Lavish Keys Life in the ultimate oceanside vacation rental in Key Largo! With a stellar ...
From $601 per night (USD)Expedia
- From $771 per night (USD)
VRBO
Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A funky and fun fisherman's private paradise that we call FISH CAMP, this property has everything needed for a large fam ...
From $771 per night (USD)VRBO
- From $1168 per night (USD)
Expedia
Casa Papa Del Mar on the Atlantic Spectacular views close to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $1168 per night (USD)Expedia
- From $511 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $511 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $226 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $214 per night (USD)VRBO
- From $655 per night (USD)
Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $655 per night (USD)Expedia
- From $347 per night (USD)
VRBO
Beautiful 3 bed\/3 bath Canal Home with Ocean Access in Key largo - 60 foot Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful Key Largo 2 story home has 3 bedrooms, 2 bathrooms upstairs with another full bathroom downstairs. This ...
From $347 per night (USD)VRBO
- From $305 per night (USD)
Expedia
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $305 per night (USD)Expedia
- From $663 per night (USD)
VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $663 per night (USD)VRBO
- From $640 per night (USD)
Expedia
Key West Beachfront Luxury 2\/2 Condo A212
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
From $640 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $175 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Keys to Paradise: A 5-Star Beachside Retreat This beautiful 3-bedroom, 2-bath condo is located in a private beachside r ...
From $329 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its n ...
From $214 per night (USD)VRBO
- From $1202 per night (USD)
Expedia
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $1202 per night (USD)Expedia
- From $714 per night (USD)
VRBO
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic 3rd Floor Ocean View Condominium Completely renovated, this unit features an entirely custom tiled unit. Full ...
From $714 per night (USD)VRBO
- From $689 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 Bedroom, 2 Bath Garden View Condo at 1800 Atlantic, Key West This beautifully renovated condo features a king bed in ...
From $689 per night (USD)Expedia
- From $547 per night (USD)
VRBO
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...
From $547 per night (USD)VRBO
- From $668 per night (USD)
Expedia
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully decorated two-bedroom, two-bath unit overlooks a tropical courtyard and garden area. The bathrooms have ...
From $668 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Joan's Caribbean Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $313 per night (USD)VRBO
- From $620 per night (USD)
Expedia
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Azul, where The Salt Life Meets Luxury! This oceanside licensed and legal vacation rental has received h ...
From $620 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated, this 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. ...
From $329 per night (USD)VRBO
- From $212 per night (USD)
Expedia
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $212 per night (USD)Expedia
- From $215 per night (USD)
VRBO
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $215 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an e ...
From $200 per night (USD)Expedia
- From $2722 per night (USD)
VRBO
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $2722 per night (USD)VRBO
- From $416 per night (USD)
Expedia
No Stairs-Private Tropical Beach-steps from condo-Hi-Speed WIFI-It's Loaded!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ask me about Covid-19 my cancellation policy. Our White Sandy Tropical Private is Beautiful and Private! I also own 3 o ...
From $416 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...
From $216 per night (USD)VRBO
- From $572 per night (USD)
Expedia
NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $572 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana Club Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the epitome of luxury at Duck Key Darling, a splendid 2-bedroom, 2-bath Townhouse Villa nestled within Hawks ...
From $468 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Couples paradise-king bed\/AC\/kayaks for your use\/fishing\/snorkeling\/diving
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Comforting king size bed with an extra room for storage or office, and perfect outdoor living space make for a great cou ...
From $242 per night (USD)Expedia
- From $266 per night (USD)
VRBO
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $266 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $240 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Breezy Half-Duplex with 35 Ft. Dock. - Cabana Club Access with Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Breezy Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $285 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Dog-friendly waterfront home with dock, pool, gas grill, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ninth Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $316 per night (USD)Expedia
- From $346 per night (USD)
VRBO
Gulf Pointe Paradise
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Pointe Paradise is a tranquil townhouse featuring a balcony with sweeping Gulf of Mexico views. Dockage is availabl ...
From $346 per night (USD)VRBO
- From $664 per night (USD)
Expedia
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $664 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Waterfront home with 24-foot dock, shared pool, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Lime on Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $279 per night (USD)VRBO
- From $284 per night (USD)
Expedia
Waterfront Home with 35-Foot Dock, Bay Views, WiFi, and Shared Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $284 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Breezy waterfront home with pool, 35-foot dock & cabana club access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Captain's Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $435 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Dog-Friendly Home with 60-Ft. Dock and Access to Cabana Club and Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Downhome Cabin by the Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $303 per night (USD)Expedia
- From $362 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock and Access to Private Beach and Shared Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ninth Street Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $362 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Waterfront home with 35-ft dock & access to Cabana Club pool & beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal-side Charisma Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $349 per night (USD)Expedia
- From $705 per night (USD)
VRBO
Waterfront Duplex with Shared Pool & Beach Access, 35-ft Dock
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 17
Breezy Palms & Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $705 per night (USD)VRBO
- From $282 per night (USD)
Expedia
Cozy Canal-Front House w\/ Free WiFi and Deck - Close to Beaches & State Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Anchors Aweigh Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $282 per night (USD)Expedia
- From $681 per night (USD)
VRBO
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with ice maker, 50" TV, refridgerator, fire p ...
From $681 per night (USD)VRBO
- From $407 per night (USD)
Expedia
Waterfront Tiny House w Pool, Beach, and Boat Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Private community with 2 private beach areas, boat ramp, heated swimming pool, beach volleyball, children's area with pl ...
From $407 per night (USD)Expedia
- From $1328 per night (USD)
VRBO
One of the very few beach houses with a daily, rental license in the Keys.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a newly remodeled four bedrooms elegant house. The property has its own private beach located in the heart of Su ...
From $1328 per night (USD)VRBO
- From $818 per night (USD)
Expedia
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $818 per night (USD)Expedia
- From $2276 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $2276 per night (USD)VRBO
- From $589 per night (USD)
Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $589 per night (USD)Expedia
- From $1295 per night (USD)
VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! Formerly La B ...
From $1295 per night (USD)VRBO
- From $514 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $514 per night (USD)Expedia
- From $1856 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1856 per night (USD)VRBO
- From $371 per night (USD)
Expedia
Sombrero Beach Home on Canal with Private Dock and Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful villa was built in 2018, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $371 per night (USD)Expedia
- From $5147 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $5147 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Oceanfront Duplex with Spectacular Views, Beach, & Dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Henry Flagler Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $675 per night (USD)Expedia
- From $493 per night (USD)
VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $493 per night (USD)VRBO
- From $4751 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $4751 per night (USD)Expedia
- From $1098 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $1098 per night (USD)VRBO
- From $3278 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $3278 per night (USD)Expedia
- From $735 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $735 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Beautiful Modern House in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $667 per night (USD)Expedia
- From $801 per night (USD)
VRBO
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well ma ...
From $801 per night (USD)VRBO
- From $944 per night (USD)
Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo \/ Pool + 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! This freshly ...
From $944 per night (USD)Expedia