Summerland Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Summerland Key, Florida on RentalSaver.com!

Summerland Key Rentals

From $1321 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 $1321 per night (USD)
VRBO
From $411 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 $411 per night (USD)
Expedia
From $179 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 $179 per night (USD)
VRBO
$Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry$
From $273 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 $273 per night (USD)
Expedia
Click For Pricing
VRBO
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple Families, Dogs OK!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Welcome to "Anchors Aweigh," your passport to the ultimate oceanfront retreat on the tranquil shores of Summerland Key. ...
Click For Pricing
VRBO
$Canalfront house with private pool, WiFi, private washer\/dryer, and central AC$
From $693 per night (USD)
Expedia
Canalfront house with private pool, WiFi, private washer\/dryer, and central AC
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $693 per night (USD)
Expedia
From $890 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 $890 per night (USD)
VRBO
From $182 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 $182 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in ...
From $413 per night (USD)
VRBO
From $479 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 $479 per night (USD)
Expedia
From $666 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 $666 per night (USD)
VRBO
From $1115 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 $1115 per night (USD)
VRBO
From $293 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 $293 per night (USD)
VRBO
From $848 per night (USD)
Expedia
Summerland Nest - Ocean view with private beach and pool
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $848 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Canal Front (Deep Water) Tropical Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $312 per night (USD)
VRBO
From $586 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 $586 per night (USD)
VRBO
From $233 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 $233 per night (USD)
VRBO
$Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights$
From $499 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 $499 per night (USD)
VRBO
From $977 per night (USD)
VRBO
WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set ...
From $977 per night (USD)
VRBO
$Relaxing 2\/2 Get Away in the Lower Keys!$
From $334 per night (USD)
Expedia
Relaxing 2\/2 Get Away in the Lower Keys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recent ...
From $334 per night (USD)
Expedia
From $260 per night (USD)
VRBO
PALM COTTAGE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $260 per night (USD)
VRBO
From $1030 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 $1030 per night (USD)
VRBO
$Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning$
From $302 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 $302 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Spacious 3-Bedroom, 2-Bath Canal Front Home on Summerland Key Airstrip
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Discover the ultimate getaway in this inviting 3-bedroom, 2-bath home, perfectly situated on Summerland Key. Ideal for f ...
From $336 per night (USD)
VRBO
From $353 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 $353 per night (USD)
VRBO
$Love Shack | Charming 2 bed\/1 bath cottage on Summerland Key$
From $166 per night (USD)
Expedia
Love Shack | Charming 2 bed\/1 bath cottage on Summerland Key
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 $166 per night (USD)
Expedia
From $621 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 $621 per night (USD)
VRBO
From $244 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Star Fish Cottage is a one bedroom unit that includes a Queen-sized bed and TV in the bedroom, a full kitchen, bath ...
From $244 per night (USD)
Expedia
From $430 per night (USD)
VRBO
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
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 $430 per night (USD)
VRBO
From $201 per night (USD)
Expedia
SEA SHELL COTTAGE UNIT #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main ...
From $201 per night (USD)
Expedia
From $378 per night (USD)
VRBO
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 $378 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Casa Morado - Bring your boat
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This 3 bedroom 1 bath home is located on Summerland Key Cove. This ground floor home is handicap accessible. Bring your ...
From $221 per night (USD)
VRBO
From $309 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 $309 per night (USD)
VRBO
From $524 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 $524 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Fishing, boating, lobstering from your backyard! Gorgeous Views & Super Private
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
**NEW TO VRBO & AIRBNB** Thank you for checking out the Key Lime Cottage - a cottage by no means!! This will be your Fl ...
From $233 per night (USD)
VRBO
From $242 per night (USD)
Expedia
FLAMINGO COTTAGE UNIT #1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with ...
From $242 per night (USD)
Expedia
From $262 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 $262 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Summerland Key Oceanfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our longtime winter tenant who has rented our house from November through April for the last 7 years has bought his own ...
From $349 per night (USD)
VRBO
$Paradise Views: Oceanfront\/Boating$
From $795 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 $795 per night (USD)
VRBO
From $743 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 $743 per night (USD)
Expedia
From $247 per night (USD)
VRBO
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 $247 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $388 per night (USD)
Expedia
$Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi$
From $492 per night (USD)
VRBO
Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Dock Holiday Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $492 per night (USD)
VRBO
$Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access$
From $314 per night (USD)
Expedia
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 $314 per night (USD)
Expedia
$**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool$
From $655 per night (USD)
VRBO
**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 $655 per night (USD)
VRBO
From $309 per night (USD)
Expedia
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 $309 per night (USD)
Expedia
From $786 per night (USD)
VRBO
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Looking to ma ...
From $786 per night (USD)
VRBO
From $546 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 $546 per night (USD)
Expedia
From $462 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 $462 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
Bedrooms:
3
Bathrooms:
3
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 $201 per night (USD)
VRBO
From $408 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 $408 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Cudjoe Bay Getaway In Paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $252 per night (USD)
Expedia
From $356 per night (USD)
VRBO
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 $356 per night (USD)
VRBO
$September Special Rate! Book Now at this canal front pool home\n\n$
From $355 per night (USD)
VRBO
September Special Rate! Book Now at this canal front pool home\n\n
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 $355 per night (USD)
VRBO
From $310 per night (USD)
VRBO
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 $310 per night (USD)
VRBO
From $264 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 $264 per night (USD)
Expedia
From $276 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 $276 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $333 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $348 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
3
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 $284 per night (USD)
Expedia
From $645 per night (USD)
VRBO
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Bedrooms:
2
Bathrooms:
3
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 $645 per night (USD)
VRBO
From $303 per night (USD)
Expedia
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 $303 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $384 per night (USD)
VRBO
From $359 per night (USD)
Expedia
water at your back door
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $359 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Enjoy Caribbean weather in the USA. Openings in Dec 2024!! Book now!
Bedrooms:
1
Bathrooms:
3
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 $272 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Island Therapy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $294 per night (USD)
Expedia
From $345 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 $345 per night (USD)
VRBO
$Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise$
From $217 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 $217 per night (USD)
Expedia
From $415 per night (USD)
VRBO
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 $415 per night (USD)
VRBO
From $335 per night (USD)
Expedia
waterfront cottage near key west, sleeps 6
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 ...
From $335 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Oceanfront Home With Large Private Deck with boat dockage
Bedrooms:
2
Bathrooms:
3
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 $420 per night (USD)
VRBO
From $462 per night (USD)
Expedia
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 $462 per night (USD)
Expedia
From $484 per night (USD)
VRBO
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 $484 per night (USD)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $456 per night (USD)
VRBO
44ft Seawall at Sportsman's Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
44ft Seawall at Sportsman's Paradise True Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba ...
From $456 per night (USD)
VRBO
From $371 per night (USD)
Expedia
WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
Bedrooms:
2
Bathrooms:
3
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 $371 per night (USD)
Expedia
$**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool$
From $616 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 $616 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
$Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key$
From $234 per night (USD)
VRBO
Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key
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 $234 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $220 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
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 $329 per night (USD)
VRBO
$Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.$
From $342 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 $342 per night (USD)
Expedia
$Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security$
From $278 per night (USD)
VRBO
Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Description: Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an ...
From $278 per night (USD)
VRBO
From $229 per night (USD)
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 ...
From $229 per night (USD)
Expedia
$Waterfront RV Lot w 35' dock in \Venture Out\. Utility hookups & beautiful views$
From $111 per night (USD)
VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\". Utility hookups & beautiful views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
35' dock on a canal in Venture Out! This is a RV lot only, there is no house. Simply drive up with your travel trailer/R ...
From $111 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $210 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 $210 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the ultimate in waterfront luxury at Caribbean Cabana, where every moment is a postcard-perfect memory waitin ...
From $407 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charmin ...
From $409 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Pelicans View - Venture Out Lot 318
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...
From $305 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Island Comfort at Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Keys Getaway! Escape to paradise with this charming 3-bd, 2-ba canal-front home, perfect for those looking to unwin ...
From $244 per night (USD)
VRBO
$NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool$
From $501 per night (USD)
Expedia
NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind at the Artist House on Tarpon Lane on Cudjoe Key! This perfect new construction waterfront home checks all the ...
From $501 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Beautiful 2-bedroom canal home with peak-a-boo open water views in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in our charming Cudjoe Key rental home! This, small dog friendly beautiful property is nestled among ...
From $217 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Paradise Palms in Cudjoe Key #635
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This tropical 2-bedroom, 2 full bathroom home has something for everyone! The kitchen boats new stainless-steel applianc ...
From $405 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Cudjoe Key like a local in this charming 1-bedroom apartment. This nice property offers a cozy living room wi ...
From $131 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Bimini Breeze - VO 313
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Bimini Breeze - VO 313 Walk to Pool and Marina! Centrally Located Charming 2Bd/1Ba This home is located on a quiet circl ...
From $328 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Tarpon Alley - Venture Out 509
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tarpon Alley - VO509 Canal Front35' Dockage Casually elegant, beautifully decorated, and fully stocked for your conveni ...
From $391 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Latitude Adjustment in Cudjoe Key #264
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled in a serene location in the Florida keys, this Oceanfront house offers breathtaking open water views that promis ...
From $629 per night (USD)
Expedia
$2 Bedroom Canal Home in Cudjoe Key, FL w\/ Private Pool & Extra Loft Space$
From $318 per night (USD)
VRBO
2 Bedroom Canal Home in Cudjoe Key, FL w\/ Private Pool & Extra Loft Space
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to ...
From $318 per night (USD)
VRBO
From $788 per night (USD)
Expedia
The Roost in Summerland Cove Isles
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The Roost in Summerland Cove Isles affectionately know as 'The Castle' is truly a gem nestled in a highly desirable neig ...
From $788 per night (USD)
Expedia

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Results: 273 Rentals