Summerland Key Rentals
- From $599 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 $599 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $263 per night (USD)Expedia
- From $224 per night (USD)
VRBO
Summerland Cove Paradise Waterfront Deep Water Canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bed 2 bath Florida Keys home. In need of a serene getaway with the ocean at arms reach? This 3 bedroom, 2 bathroom hom ...
From $224 per night (USD)VRBO
- From $123 per night (USD)
Expedia
Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summerland Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $123 per night (USD)Expedia
- From $261 per night (USD)
VRBO
Canalfront house with private pool, WiFi, private washer\/dryer, and central AC
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $261 per night (USD)VRBO
- From $344 per night (USD)
Expedia
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple Families, Dogs OK!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to "Anchors Aweigh," your passport to the ultimate oceanfront retreat on the tranquil shores of Summerland Key. ...
From $344 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
Summerland Breeze - Three house retreat, perfect for multiple families
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $1000 per night (USD)VRBO
- From $152 per night (USD)
Expedia
Tropical Island Sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful tropical island retreat! Enjoy all the the splendor the lower Keys have to offer from our home ...
From $152 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in ...
From $230 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Location Location! Beautiful views from every angle. Summerland Cove rare point
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
If you’re looking for a coastal experience with a modern peaceful clean stay this home is for you. Stay comfortably in S ...
From $415 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Beach Bliss, Oceanfront with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...
From $550 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Oceanfront house private beach & protected canal dockage for up to 36' boat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerl ...
From $250 per night (USD)VRBO
- From $715 per night (USD)
VRBO
Summerland Nest - Oceanfront with pool
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $715 per night (USD)VRBO
- From $960 per night (USD)
VRBO
Luxurious, Private, Oceanfront, Gated Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Stunning 1 acre oceanfront gated estate with lush landscaping, beach and extreme privacy due to the adjacent wildlife re ...
From $960 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Mariners Cove - The Kraken House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet C ...
From $600 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Canal Front (Deep Water) Tropical Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $220 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Relax at the flying hogfish
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West an ...
From $175 per night (USD)VRBO
- From $430 per night (USD)
VRBO
Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawal ...
From $430 per night (USD)VRBO
- From $886 per night (USD)
VRBO
WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set ...
From $886 per night (USD)VRBO
- From $199 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Green Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $199 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recently renovated hom ...
From $286 per night (USD)VRBO
- From $900 per night (USD)
VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $900 per night (USD)VRBO
- From $347 per night (USD)
VRBO
Florida Keys Paradise!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the ultimate vacation experience? Our vacation home has everything you need to relax and have fun. We are lo ...
From $347 per night (USD)VRBO
- From $299 per night (USD)
Expedia
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 pe ...
From $299 per night (USD)Expedia
- From $150 per night (USD)
VRBO
SEA SHELL COTTAGE UNIT #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor ...
From $150 per night (USD)VRBO
- From $305 per night (USD)
Expedia
Large 5 Bedroom Canal Home in Summerland Key, FL with Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited ...
From $305 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront villa with pool, outdoor areas, home gym, & fillet station
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 14
Tarpon Ranch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingVRBO
- From $153 per night (USD)
Expedia
Boat Dock \/ Private Airstrip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your Canal Front Oasis on Summerland Key! Dock your boat along the sea wall, offering convenient access to wo ...
From $153 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Recently Renovated Home With Deepwater Canal
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first can ...
From $200 per night (USD)VRBO
- From $540 per night (USD)
VRBO
Beautiful Oceanfront Villa with Pool and near Key West, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home wi ...
From $540 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Love Shack | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
While not directly waterfront, this retreat boasts convenient access to a nearby boat ramp, making it ideal for boating ...
From $124 per night (USD)VRBO
- From $189 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PINK COTTAGE UNIT #3 - Sleeps 4 ACCOMODATIONS: UNIT #3 comes with TV, AC, WIFI & Full Kitchen. full kitchen. Enjoy th ...
From $189 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Summerland Key Oceanfront
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please check out the new updated photos of all the repairs and updates. The house now has new impact windows and doors, ...
From $300 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Paradise Views: Oceanfront\/Boating
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely e ...
From $650 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Summerland Keys Upgraded Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful oasis on the water with plenty of room for your boat and trailer! With 50 f ...
From $270 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Windswept Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly renovated 3 bedroom, 3 bathroom home with stunning open water views! This modern home is perfect fo ...
From $465 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Deep water Boating ~ Bay Views ~ 3 bed 2 bath + outside shower
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Thank you for checking out the Key Lime Cottage! This deceivingly spacious 3 bedroom 2 bath home is tastefully furnish ...
From $190 per night (USD)VRBO
- From $183 per night (USD)
Expedia
FLAMINGO COTTAGE UNIT #1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal ...
From $183 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Summerland Cottage- Our Little Piece of Paradise with an Old School Key Vibe!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...
From $233 per night (USD)VRBO
- From $289 per night (USD)
VRBO
Summerland Key House Open Air Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathro ...
From $289 per night (USD)VRBO
- From $170 per night (USD)
VRBO
Seabreeze Escape WF RV Lot 489
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Seabreeze Escape WF RV Lot 489 Open Water Views! 35' Dockage with Tropical Landscaping!! Fish and swim right from your ...
From $170 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Emerald Seas - Florida Keys Ocean Front Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $425 per night (USD)Expedia
- From $295 per night (USD)
VRBO
Stunning Oceanfront Keys Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1,200-square foot home is a gorgeous ocean front property just minutes from back country and oceanside fishing. Tuc ...
From $295 per night (USD)VRBO
- Click For Pricing
Expedia
Stylish & Modern Summerland Key Private Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the very best of the Florida Keys from the comfort & convenience of this upgraded waterfront retreat! Perfectly ...
Click For PricingExpedia
- From $99 per night (USD)
VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
35' dock on a canal in Venture Out! This is a lot only there is no house. Simply drive up with your travel trailer/RV/5t ...
From $99 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Bimini Breeze in Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your dream vacation destination! This beautifully updated and remodeled 2-bedroom, 1-bathroom rental property ...
From $275 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Our Florida Keys \"Sea-Cove\"! Canal front, Boat dockage, Pool, Private!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make our happy place, your happy place! Escape to this canal front retreat and leave your worries behind. This 2-bedr ...
From $270 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Come stay and play in the Florida Keys!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This colorful, tropical vacation home has two bedrooms, one bath, with new 2022 central air conditioning, and is locate ...
From $235 per night (USD)Expedia
- From $304 per night (USD)
VRBO
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 $304 per night (USD)VRBO
- From $310 per night (USD)
Expedia
Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dock Holiday Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $310 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous stilt home with beautiful ocean views. This Lobstering paradise is just 1 house down from open water on a deep ...
From $225 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Nice home on Atlantic side of Cudjoe Key!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $180 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This oceanside property has 2 beds 2 baths and sleeps 6 with all updated appliances and furniture. There are kayaks and ...
From $275 per night (USD)VRBO
- From $280 per night (USD)
Expedia
**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 $280 per night (USD)Expedia
- From $326 per night (USD)
VRBO
**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + 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! What could be ...
From $326 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We invite you to come and relax at Torchview Lookout, your own private waterfront retreat! This 3 bedroom / 2 bathroom ...
From $400 per night (USD)Expedia
- From $166 per night (USD)
VRBO
Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The Blue Marlin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $166 per night (USD)VRBO
- From $390 per night (USD)
Expedia
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool
- 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 $390 per night (USD)Expedia
- From $636 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 $636 per night (USD)VRBO
- From $275 per night (USD)
Expedia
WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy our little piece of paradise! Casa Del Sol is a cozy 820 square foot home that has everything you want for the per ...
From $275 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Canal front home @ Venture Out Resort in the Florida Keys!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** SUPER beautiful canal front home with open wa ...
From $385 per night (USD)VRBO
- Click For Pricing
Expedia
Calypso Cottage Awaits!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your d ...
Click For PricingExpedia
- From $359 per night (USD)
VRBO
Oceanfront Home With Large Private Deck with boat dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy boating, swimming or just the ocean view in the greatest of privacy. Dinner and entertainment in Key West is a sho ...
From $359 per night (USD)VRBO
- From $285 per night (USD)
Expedia
Sirena Key Cottage in Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $285 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Kelly's Kabin - Adorable Private Summerland Key Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $225 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $225 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Cudjoe Bay Access Vacation House In Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $200 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Casa Del Mar in Venture Out Unit 253
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VO253 Open Water Views 35' Dockage Sparkling Clean 2Bd/1Ba Vacation Home! THIS IS ONE OF THE NICEST UNITS IN ALL OF VENT ...
From $273 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Pool Home on Tranquil Private Cruikshank Island available for MARCH 2024!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $300 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $210 per night (USD)Expedia
- Click For Pricing
VRBO
Blue Chill Vacation!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This tropical vacation home offers two bedrooms, one bathroom and is located in a gated community just 19 miles form Key ...
Click For PricingVRBO
- From $178 per night (USD)
Expedia
Seascape Vacation!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful vacation spot on Cudjoe Key perfect for you and your family. This wonderful one bedroom home filled with color ...
From $178 per night (USD)Expedia
- From $218 per night (USD)
VRBO
Seas The Day in Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A cozy and small mobile home with Marina access and a boat ramp. With almost perfect weather you experience in the Keys ...
From $218 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay with us at VENTURE OUT, a fantastic safe, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $199 per night (USD)Expedia
- From $225 per night (USD)
VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Salty Sailfish, a magnificent canal-front home nestled on Cudjoe Key. With updated furnishings and a comm ...
From $225 per night (USD)VRBO
- From $327 per night (USD)
Expedia
water at your back door
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $327 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Enjoy Caribbean weather. Last minute opening beginning 5\/19\/24! Enjoy the Keys!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $200 per night (USD)VRBO
- From $220 per night (USD)
Expedia
Island Therapy
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $220 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Judy's place at Venture Out
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Judy's Place is located in the Venture Out Resort. A quiet little secret escape just 20 miles from Key West. Judy's Plac ...
From $225 per night (USD)VRBO
- From $175 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 $175 per night (USD)Expedia
- Click For Pricing
Expedia
Kokomo 3\/2 home on canal quick boating access Cudjoe Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully remodeled 3 bedroom 2 bath home with 60’ concrete dockage in Cudjoe Key. Home is perfectly appointed with ev ...
Click For PricingExpedia
- From $300 per night (USD)
Expedia
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $300 per night (USD)Expedia
- From $261 per night (USD)
VRBO
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $261 per night (USD)VRBO
- From $169 per night (USD)
Expedia
Tropical Getaway in Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bedr ...
From $169 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Ocean Front Modern Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $430 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water views. Located on the ...
From $302 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Cozy, Perfect Conch Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Everything what you need for perfect vacation you will find in the cozy walls of Conch Cottage. Open great room, washer ...
From $140 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Captain’s Quarters located on the beautiful Cudjoe Bay. This waterfront estate checks all the boxes and is ...
From $400 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
You found it!! Bring your boat! Charming cottage located in Venture Out, resort style community located on Cudjoe Key, ...
From $235 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Latitude Adjustment | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom/2 bathroom canalfront home on Summerland Key just a few homes in from open water. Vaulted ceilings, updated an ...
From $199 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Paradise Found | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stai ...
From $170 per night (USD)VRBO
- From $170 per night (USD)
Expedia
Blackbeard`s Hideaway: Cozy canalfront cottage is an angler's dream on Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $170 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Foster`s Folly | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilt ...
From $282 per night (USD)VRBO
- From $282 per night (USD)
Expedia
Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is your home away from home. Beautiful 3 story home with spacious master bedroom and bathroom located on top floor ...
From $282 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Description: Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an ...
From $140 per night (USD)VRBO
- From $145 per night (USD)
VRBO
RELAX IN HEAVENLY PARADISE - CUDJOE KEY GETAWAY\n3 MINUTES TO OPEN WATERS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wow!!! Our new spacious 3 bedroom 2 full bath home on a 60 foot wide deep water canal with a 60 foot dock only 1500 fee ...
From $145 per night (USD)VRBO
- From $279 per night (USD)
VRBO
Location, location, location briefly describes this small piece of Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on a private and quiet open water lot, this charming cottage offers a wonderful view even to those people who do ...
From $279 per night (USD)VRBO
- From $216 per night (USD)
VRBO
Canal Front Home, Heated Pool, Fisherman's Dream
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sailfish Escape is a beautiful 3 bedroom, 2 bath 1400 sq ft home on a peaceful canal. Beautiful large fully stocked kitc ...
From $216 per night (USD)VRBO
- From $296 per night (USD)
VRBO
MANATEE HIDEAWAY 35' Seawall with Easy Ocean Access Atlantic Open Water or Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Our charming 2 bedroom, 2 bath stilt home has just been completed October 2019, two years after Hurricane Irma blew away ...
From $296 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to eithe ...
From $200 per night (USD)VRBO