
Vacation rentals with a pool in Cudjoe Key
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Top-rated rentals with a pool in Cudjoe Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Rise And Shine On The Water
Spectacular sunrise view! Room to park one vehicle & have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans., GRILL, TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

Beautiful Cottage & Amenities in Gated Community
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Fisherman's Paradise Cudjoe Key
Waterfront home on Cudjoe Key in beautiful Key West, Florida. This two bedroom two bath home features a 30' dock for your boat so you can maximize your time on the water. Prepare your catch in the fully equipped kitchen featuring a gas range and full size fridge. Enjoy outdoor dining on the back patio just steps from the canal. The open floor plan is perfect for spending quality time with family indoors, when you're not enjoying the many outdoor amenities Venture Out community has to offer.

Ocean~View w/ Dock, Pool, Kayaks, King Bed
Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

MARCH $Save $ Oceanfront 4 Bikes/2Kayaks. KING bed
*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

35’ dock/Completely Remodeled VO 366
Dock your boat and enjoy open water views. Our 2 bedroom 2 bathroom newly remodeled home is perfect for your family get away or a couples retreat. Home comes with 2 kayaks and 2 bikes. The gated community offers pool, beach area, hot tub, pickle ball, playground area, basketball and a recreation room. THERE IS A $125 RESORT FEE DUE AT THE GATE UPON ENTRY.
Popular amenities for Cudjoe Key rentals with a pool
House rentals with a pool

Pelican's Roost, Waterfront comfort at Venture Out

Beach House, Private Pool & Dock, Gulf Sunset view

Waterfront Beach House with Dock & Heated Pool!

Bohemian Beach Bungalow

P45 - Spacious 5 bedroom, 4 bath home with spectac

Casa Marquez

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor

Luxury 5 bdrm/6bth new in 2024 !
Condo rentals with a pool

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Tropical Escape at Sunrise

Affordable Beachfront Luxury Condo Sleeps 6

Fully renovated 2/2 bath condo w/ shared pool!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Duval Street Suites on Duval Free Parking and heat

Beachside Unit 33-Private Tropical Beach Plus Pool

Vacation home Island Suite 16
Other vacation rentals with a pool

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Lower Keys Paradise

Island Oasis ~ YOUR Paradise Awaits!

OCEANIA... water front cottage retreat ~

Tiny Fish Haus

Comfortable Home w/ Amenities in Gated Community

Happy Hibiscus Home
When is the best time to visit Cudjoe Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$64,414 GYD | G$67,969 GYD | G$66,296 GYD | G$61,695 GYD | G$54,375 GYD | G$54,793 GYD | G$60,440 GYD | G$59,185 GYD | G$51,656 GYD | G$50,192 GYD | G$56,466 GYD | G$64,623 GYD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about vacation rentals with a pool in Cudjoe Key

Total vacation rentals
Explore 240 vacation rentals in Cudjoe Key

Nightly prices starting at
Cudjoe Key vacation rentals start at G$10,457 GYD per night before taxes and fees

Verified guest reviews
Over 5,760 verified reviews to help you choose

Family-friendly vacation rentals
180 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
210 of Cudjoe Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cudjoe Key rentals

4.8 Average rating
Cudjoe Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Long Beach
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- Conch Key
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
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