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 $639 per night (USD)
VRBO
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a ...
From $639 per night (USD)
VRBO
From $699 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 $699 per night (USD)
Expedia
From $528 per night (USD)
VRBO
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 $528 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Waterfront home with numerous amenities on popular Cudjoe Key!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Crystal Clear Canal front home with open water view! Home is located in a desirable community called Venture Out. Fully ...
From $385 per night (USD)
Expedia
From $453 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 $453 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy ...
From $528 per night (USD)
Expedia
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 $215 per night (USD)
Expedia
Relaxing and Inviting home in gated community
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in ta ...
From $215 per night (USD)
Expedia
$OCTOBER\/NOVEMBER SPECIAL! FISH, SWIM, RELAX FOR ONLY 3000+tax MONTH$
From $215 per night (USD)
VRBO
OCTOBER\/NOVEMBER SPECIAL! FISH, SWIM, RELAX FOR ONLY 3000+tax MONTH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to 'Shangri-La' This is where you can RELAX and ENJOY the TRANQUIL beauty of the sun, sea & sand of the Florida ...
From $215 per night (USD)
VRBO
From $7530 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 $7530 per night (USD)
Expedia
From $249 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 $249 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 $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 $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
$Tropical Island Paradise W \/ Open Water Views!$
From $276 per night (USD)
VRBO
Tropical Island Paradise W \/ Open Water Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please see our other property if you do not see your dates available! Property # 2092236 https://www.vrbo.com/2092236?ad ...
From $276 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Cudjoe Key, FL RV Resort RV Lot
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
RV lot in Cudjoe Key, FL RV Resort, 35×70, full hook-up. Beautiful community, great relaxing location, close to shopp ...
From $225 per night (USD)
VRBO
Click For Pricing
VRBO
Atlantic Ocean Views - Venture Out 579
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Ocean Views - Venture Out 579 Lovely Stilt 2Bd/2Ba with 35' Dockage This beautiful sparkling clean 2Bd/2Ba stil ...
Click For Pricing
VRBO
$Love Shack | Charming 2 bed\/1 bath cottage on Summerland Key$
From $161 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 $161 per night (USD)
Expedia
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VRBO
Fisherman's Delight! - Venture Out Unit 410
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO410 Fisherman's Delight! 35' Dockage 2Bd/2Ba with Covered Porch! This sparkling clean and beautiful canalfront home f ...
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VRBO
From $388 per night (USD)
VRBO
Keys Time #437 - Cudjoe Key, Oceanfront Community
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Keys Time!! Slow it down. Unwind. Enjoy the Island Life! This Beautifully furnished 2 bedroom 2 bath canal ...
From $388 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 $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 $506 per night (USD)
VRBO
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! From the mome ...
From $506 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Sailfish Dream on Cudjoe Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 2'nd floor 2 bedroom/2 bath home is your tropical getaway. The home is at MM 23 giving you Key West or Marathon eq ...
From $237 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Peaceful ocean front cottage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...
From $278 per night (USD)
VRBO
From $212 per night (USD)
Expedia
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 $212 per night (USD)
Expedia
$RV resort site\/rvsite\/spot\/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT$
From $107 per night (USD)
VRBO
RV resort site\/rvsite\/spot\/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV RESORT SPOT. BIG Rig Friendly discount per month when booking 1ST to the 1ST of the month RV RESORT SITE ...
From $107 per night (USD)
VRBO
From $486 per night (USD)
Expedia
SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 ...
From $486 per night (USD)
Expedia
From $680 per night (USD)
VRBO
Spanish Queen @Venture Out, Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnish ...
From $680 per night (USD)
VRBO
$3\/2 Home on Canal with Dock and Ocean Access$
From $216 per night (USD)
VRBO
3\/2 Home on Canal with Dock and Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
On canal with ocean access to Atlantic and Gulf sides. 3 bedroom 2 full bath renovated canal front Cudjoe Key beach home ...
From $216 per night (USD)
VRBO
From $253 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 $253 per night (USD)
VRBO
From $463 per night (USD)
VRBO
Rise & Shine with spectacular sunrise views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Perfect spot for fishing, lobstering, and snorkeling with a spectacular sunrise view! There is room to park one vehicle, ...
From $463 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Mad Mahi Canal with pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...
From $515 per night (USD)
VRBO
$Sea La Vie - Monthly Vacation Rental - Oceanfront 3BD\/3BA RealKeyWest$
From $252 per night (USD)
Expedia
Sea La Vie - Monthly Vacation Rental - Oceanfront 3BD\/3BA RealKeyWest
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Sea La Vie, an elevated oceanfront paradise available for rent. Nestled in the picturesque Cudjoe Bay, this 3 ...
From $252 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Ocean View Splendor on Summerland Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened ...
From $294 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
From $419 per night (USD)
VRBO
Waterfront Venture Out Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Mandatory $125 Fee paid to Venture Out Community upon arrival. Waterfront home with concrete seawall for boat dockage. ...
From $419 per night (USD)
VRBO
$RV Lot Venture Out, 35x69' Accommodates Large\/Oversized RVs$
From $136 per night (USD)
VRBO
RV Lot Venture Out, 35x69' Accommodates Large\/Oversized RVs
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Welcome to this remarkable and generously spacious RV Lot nestled within the beautiful community of Venture Out on Cudjo ...
From $136 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Open water pool home 25miles from Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Relax by the pool with heater/chiller, jets and sundeck. Over 100' of seawall on deep water. Kayaks on-site. Second flo ...
From $460 per night (USD)
VRBO
From $487 per night (USD)
VRBO
Sun Bake @ Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Canal front home in a gated community. Large screened in porch. Freshly updated deck furniture, docking post, and fish c ...
From $487 per night (USD)
VRBO
$Sunshine 23 | Dog-friendly 2 bed\/2 bath canalfront boating home on Cudjoe Key$
From $239 per night (USD)
VRBO
Sunshine 23 | Dog-friendly 2 bed\/2 bath canalfront boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating ...
From $239 per night (USD)
VRBO
From $748 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 $748 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Tropical paradise on open water 35 ft seawall in beautiful Venture Out Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ocean Front 35’ Seawall – Spectacular views from this 2 Bedroom 2 Bathroom ocean front stilt home! This home features a ...
From $421 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Venture Out- Million Dollar Island Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oceanfront Home, Pool Access/50 Ft Dock Fresh & Fabulous best describes this island listing . This fantastic Ocean home ...
From $301 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Oceanfront RV Lot with 40' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Bring your own RV and experience the majestic beauty of the Florida Keysat this beautiful Oceanfront RV Lot! Lot feature ...
From $152 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Water Lovers Paradise
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This newly renovated vacation home on a canal in Cudjoe Key is a stunning retreat that offers the perfect blend of comf ...
From $194 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Base Camp - Boaters welcome! Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Base Camp on Cudjoe Key - 2 Bedroom Canal Front home in a perfect, convenient location for excellent boating a ...
From $191 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Canal front RV lot quick access to Atlantic Ocean or Gulf
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Canal front RV lot with 35’ dock. Cleats , fish cleaning table, 110 volts,50 and 30 amp hook up and sewer service on sit ...
From $189 per night (USD)
Expedia
From $149 per night (USD)
VRBO
RV Lot 621 Venture Out
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the tranquility of this freshly landscaped RV lot nestled within Venture Out. This spacious 35' by 70' lot fe ...
From $149 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Blue Mind - Venture Out Unit 225
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BLUE MIND - VO225 35' Dockage on Y-shaped Canal Sparkling Clean Kayak & WiFi This beautifully decorated vacation home is ...
From $310 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Endless Water Views - Venture Out 526
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Endless Water Views - Venture Out 526 Newer Stilted 2Bd/2Ba Home with WIFI 35' Dockage Open Water Views! This newer cons ...
From $444 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Cozy Venture Out Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
MANDATORY $125 FEE NOT INCLUDED, PAID TO VENTURE OUT COMMUNITY UPON ARRIVAL. One bedroom home with all that you need. ...
From $357 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shangri-la in the Keys! Enjoy the water views and a 45' dock space! VO unit 413 - 2Bd/2Ba Stilt Home Newly renovated s ...
From $416 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Treasure Isle at Parks End - Venture Out 062
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Treasure Isle at Parks End - Venture Out 062 Southern Location Walk to Ocean! This sparkling clean and bright 2 Bedroom ...
From $336 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Piece Of Eight - Venture Out 279
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Piece Of Eight - Venture Out 279 Stilt 2Bd/2Ba 35' Dockage Close to Everything! Recently updated 2 BR/2 BA stilt home ...
From $421 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Pelican's Roost, Waterfront comfort at Venture Out
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
About this space Pelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles f ...
From $444 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Dickey's Dockside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Escape to Dickey's Dockside Retreat. This waterfront paradise in the Florida Keys offers a private dock, perfec ...
From $340 per night (USD)
Expedia
From $580 per night (USD)
VRBO
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property that won’t disappoint! Full ...
From $580 per night (USD)
VRBO
$Waterfront Oceanside 200' Seawall 3\/2 Sleeps 6$
From $323 per night (USD)
VRBO
Waterfront Oceanside 200' Seawall 3\/2 Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forwa ...
From $323 per night (USD)
VRBO
Click For Pricing
VRBO
Waterfront Oceanside 200' Seawall efficiency Sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hello ! My name is Debra and I run our account for our family. We love our salty slice of paradise and I look forward t ...
Click For Pricing
VRBO
$Ocean\/Canal Views 21ft Dock - Venture Out #357$
From $331 per night (USD)
Expedia
Ocean\/Canal Views 21ft Dock - Venture Out #357
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Ocean/Canal Views 21' Dockage 2Bd/2Ba with Double Porches, Large Landscaped Yard! Island Breeze is a fabulous ...
From $331 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Oceanfront Empty RV lot - 59' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Stunning Oceanfront EMPTY RV LOT: Perfect for Boating Enthusiasts! Dive into an oceanfront experience like no other! Thi ...
From $189 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...
From $292 per night (USD)
Expedia
From $236 per night (USD)
VRBO
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 $236 per night (USD)
VRBO
$Waterfront RV Lot w 35' dock in \Venture Out\. Utility hookups & beautiful views$
From $124 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 $124 per night (USD)
VRBO
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 $223 per night (USD)
VRBO
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 $223 per night (USD)
VRBO
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 $520 per night (USD)
VRBO
Come relax at Sandy Bottom Beach Cottage!!!!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Beautiful Summerland Key!! Two houses from the Atlantic Ocean. Enjoy boating, kayaking, swimming in the 28' x 9' swim s ...
From $520 per night (USD)
VRBO
$Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning$
From $302 per night (USD)
Expedia
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)
Expedia
From $223 per night (USD)
VRBO
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Perfect fishing and boating location on Kemp Channel between Cudjoe Key and Summerland Key. New Pool Installed August ...
From $223 per night (USD)
VRBO
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 $271 per night (USD)
VRBO
Coastal Oasis, Canal front
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
COASTAL OASIS is just for you. This three-bedroom two-bath canal-front home offers a comfortable base for your Keys adve ...
From $271 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Cudjoe Bay Overlook
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This really nice custom Keys home is located in a very quiet area with good boating access to both the Atlantic with its ...
From $269 per night (USD)
VRBO
From $647 per night (USD)
VRBO
Latitude Adjustment in Cudjoe Key
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 $647 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Cuddie Cottage: 2BR Waterfront Home in Venture Out Resort, Open Water Views, Shared Pool & Hot Tub!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Cuddie Cottage, your charming haven nestled within the picturesque Venture Out resort on Cudjoe Key. This del ...
From $323 per night (USD)
Expedia
$COCONUT TELEGRAPH ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!$
From $624 per night (USD)
VRBO
COCONUT TELEGRAPH ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CUDJOE CUTIE WITH AMENITIES GALORE… Sweeping views of the dazzling turquoise waters of the Florida Keys will ignite your ...
From $624 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Sunset Views, oceanfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the sunsets on Sarcarma Bay from this rustic home in a tropical setting with an open waterfront and canal access. ...
From $352 per night (USD)
VRBO
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 $330 per night (USD)
VRBO
Lime in the coconut
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You put the "LIME IN THE COCONUT" and add a little fun! Great times to be had in this very nice 3 bedroom 2 bath custom ...
From $330 per night (USD)
VRBO
From $306 per night (USD)
VRBO
House, relaxing space,waterfront at Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful house located in Cudjoe Key, one of the most beautiful and relaxing keys in the area with a canal and acc ...
From $306 per night (USD)
VRBO
$Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!$
From $337 per night (USD)
Expedia
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...
From $337 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Crab Shack
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This cozy home on Cudjoe is exactly what you are looking for if you want good boating. The canal it is on opens up to Ke ...
From $252 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Spectacular Sunsets, 3 bed, 2 bath with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape completely in this open and airy 3 bedroom 2 bath oceanfront pool home. Situated on the northern shore of Sarcarm ...
From $352 per night (USD)
VRBO
From $549 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 $549 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Tropical Island Getaway - VO196
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO196 2B/2Ba Tropical Island Getaway! Ocean Views with 35' Seawall! Enjoy breathtaking ocean views from this midrise ...
From $515 per night (USD)
Expedia
From $605 per night (USD)
VRBO
3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the ...
From $605 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Beautiful 3 bed 2 bath deep water canal front home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to th ...
From $269 per night (USD)
VRBO
From $211 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 $211 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 $460 per night (USD)
VRBO
PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location Location Location! Welcome to our very special community Summerland Key. WSummerland is one of the best fish ...
From $460 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Paradise in the Fabulous Florida Keys - Fishing and Dive capital of the world.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Beautiful open water views with gorgeous Sunsets across Cudjoe Bay. Enjoy happy hour overlooking the canal and dock or o ...
From $247 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $387 per night (USD)
VRBO
Pelican's Paradise #507 - Oceanfront Community!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fly away to Pelican's Paradise! A modern 1 bedroom, 1 bath cottage nestled in the private, gated community of Venture O ...
From $387 per night (USD)
VRBO
$Waterfront home with boat\/canal access, screened lanai, & renovated interior$
Click For Pricing
VRBO
Waterfront home with boat\/canal access, screened lanai, & renovated interior
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For Pricing
VRBO
From $574 per night (USD)
Expedia
Beautiful Cottage & Amenities in Gated Community
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture O ...
From $574 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Sunny Hideaway - Venture Out Unit 276
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunny Hideaway - Venture Out Unit 276 This beautifully decorated home is located on the water and is located within walk ...
From $481 per night (USD)
VRBO
From $618 per night (USD)
VRBO
Slow M'Ocean #54 - Oceanfront Home - Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in SLOW M'OCEAN ~ This stunning, direct ocean front home located in the private, gated community of V ...
From $618 per night (USD)
VRBO

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Results: 269 Rentals