50 Best Vacation Rentals in Osa Peninsula - Holiday Lettings - Cabins

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Puerto Jimenez
28 properties
Drake Bay
28 properties
Cabo Matapalo
16 properties

Osa Peninsula

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77 Vacation rentals

(16) Excellent 

19

Vacation bungalow rental

Osa Peninsula / Cabo Matapalo

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Have your own private off-the-grid cabin in the jungle of Costa Rica's Osa Peninsula, and just steps from a secluded beach. You'll see monkeys off your front porch, pick your own fresh mangoes off the tree in your front yard, and go for a surf at an excellent point brea …see more

from $85 / night

$500 - $920 / week

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from $85 / night

(7) Excellent 

21

Vacation bungalow rental

Osa Peninsula / Cabo Matapalo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Have your own private off-the-grid cabin in the jungle of Costa Rica's Osa Peninsula, and just steps from a secluded beach. You'll see monkeys off your front porch, pick your own fresh mangoes off the tree in your front yard, and go for a surf at an excellent point brea …see more

from $85 / night

$500 / week

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from $85 / night

9

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
  • Private garden
We are locate in Drake Bay ., north side from Corcovado National Park in la Peninsula de Osa Puntarena CostaRica. casita cecropia is locate 700 m eter from the beach or 400 meter from Drake store ., we are local family that live in Drake Bay area and now …see more

Pricing unknown

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Pricing unknown

14

Vacation home rental

Osa Peninsula / Puerto Jimenez

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Private garden
This charming open air beach house is only steps from the ocean. Watch the sunrise from the comfort of your bed and listen to the Scarlet Macaws as they serenade you from their favorite tree in the area, right next to the house!! Nestled in the curve of a secluded bay …see more

from $120 / night

$725 - $1145 / week

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from $120 / night

5

Vacation b&b in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
Bed and Breakfast in charming house .Climatisation and refrigerator in each room. Near the center of the village, the beach (5 minutes walk) and the entrance to the Corcovado Park. Private garden or rub macaws, toucans, squirrels and many birds with a sitting area and h …see more

from $45 / night

$315 / week

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from $45 / night

(1) Excellent 

43

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Ask about pets
Visitors repeatedly say that Casa Sonrisa and our other bamboo houses are exceptional, and have made it a Travelers Choice Winner on TripAdvisor for four years. This year it was among TripAdvisor’s top hotels for families in all Costa Rica and Central America. Located o …see more

from $115 / night

$785 - $2766 / week

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from $115 / night

17

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Jungua (recently completed) was built by a master timber framer and everything about it screams QUALITY. It is sustainably built and has an extremely low impact on the environment. The house is exclusively solar powered yet features many amenities one would expec …see more

from $300 / night

$2100 - $3500 / week

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from $300 / night

(1) Excellent 

14

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Casa Troya is an open air, bamboo house. The design reflects the typical home design of the Osa Peninsula with its half-height walls and natural, local building materials. It has a fully equipped kitchen and bathroom downstairs, and a loft partitioned into two bedrooms …see more

from $100 / night

$650 - $1300 / week

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from $100 / night

(13) Excellent 

28

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Wake to the sound of howler monkeys, toucans, scarlet macaws & the running river below! Sip your coffee whilst watching giant blue morphs dance in the early morning sunlight! Smell the fragrant frangipani & ylang ylang! Experience the intense, inspiring majesty & the Pu …see more

from $100 / night

$500 - $1400 / week

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from $100 / night

(7) Very Good 

26

Vacation home accommodation

Osa Peninsula / Drake Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.001 mi
  • Child friendly
This AIR CONDITIONED home is a 2 bedroom house with magnificent hilltop views of Drake Bay. This home boasts of the best view of Drake Bay of all the homes along the beach. Private and central to all necessary amenities. Full kitchen, free WIFI and an amazing backyard p …see more

from $100 / night

$650 - $1512 / week

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from $100 / night

(4) Excellent 

21

Vacation cottage rental

Osa Peninsula / Drake Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
A stay at Sierpe del Pacifico is Costa Rica at its finest...remote and comfortable accommodations...nature in its purest form all around you...adventure rich...much more affordable for families than the Drake Bay Eco-Lodges This is your chance to completely escape the …see more

from $89 / night

$550 - $1220 / week

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from $89 / night

(18) Excellent 

32

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Located in an area of Costa Rica known world wide for the diversity of it's flora and fauna, The Osa Penninsula. This wonderfully ecologically balanced area is incredibly essentially free of Mosquitos given the number of Bats and Birds that are the Mosquito's predator …see more

from $125 / night

$700 - $1400 / week

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from $125 / night

(12) Excellent 

39

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Casa Bella is a two-story three bedroom, large balcony home situated two minutes from the beach and a ten minute drive to the airport. The houses proximity to the Gulfo Dulce is perfect for day trips to view whales, dolphins, and experience the natural beauty of the la …see more

from $100 / night

$1400 - $2100 / week

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Responds fast!
avg. 2 hours 6 minutes

from $100 / night

(15) Excellent 

17

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This newly built small house is fully self contained with kitchen, bedroom, 3 piece bathroom, plumbed hot water to all faucets, outside roofed porch with hammocks, handmade wooden bench-swing, patio table and chairs. It is built using locally cultivated, sustainable ha …see more

from $135 / night

$945 / week

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from $135 / night

(4) Excellent 

24

Vacation log cabin rental

Osa Peninsula / Puerto Jimenez

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Casita Tranquila is located in a tropical setting on a secluded beach on the Osa Peninsula South of Puerto Jimenez on the way to Corcovado National Park. There is room for up to 5 people. The house features two bedrooms, a kitchen, living room, porch/deck, and private …see more

from $99 / night

$693 - $1218 / week

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from $99 / night

11

Drake Bay Vacation home rental

Osa Peninsula / Drake Bay

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
SuChante is a fully equipped two story house in the rainforest. The Kitchen and Lounge with Sofa, Library and Board Games are located downstairs. As well as the outdoor dining area.An anexion with a private room and own bathroom is located downstairs too. Upstairs there …see more

from $80 / night

$560 / week

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Responds fast!
avg. 2 hours 43 minutes

from $80 / night

(20) Excellent 

23

Vacation villa in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Enjoy the highs of Costa Rica, at the beautiful hilltop Villa Tres Palmas, boasts a Panoramic 180 degree view of the Pacific-Ocean, the Golfo Dulce and all the way to Panama, unlike no other. And nestled into the most lush animal filled jungle rain-forest of the Osa …see more

from $500 / night

$3500 - $8940 / week

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from $500 / night

16

Vacation condo in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Air conditioning
San Jose Airport is a short 15 minute trip by car to Escazu, where our condo accommodations are. The condo is a newly finished 2 bedroom 2 bath living quarters in the first building of the Torres de Colina complex. We like to recommend this destination as a starting p …see more

from $170 / night

$569 / week

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from $170 / night

13

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
Casa Rio Sombrero is custom-finished with fine hardwoods, has an open floor plan, and a beautiful thatched roof. The upstairs has two bedrooms containing king-sized, netted beds. A twin bed can be added to one of these rooms for extra sleeping space. Downstairs, there …see more

from $150 / night

$1000 - $1650 / week

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from $150 / night

33

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.08 mi
  • Child friendly
Visitors repeatedly say that Casa Pina is exceptional. So take a walk on the wild side! This off-grid Costa Rica beach rental offers nature lovers, surfers and fishermen an ideal vacation. It sits on four acres of beautiful beachfront and world-class SUP surfer's dream …see more

from $125 / night

$851 - $2766 / week

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from $125 / night

11

Drake Bay Vacation bungalow rental

Osa Peninsula / Drake Bay

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Two story loft style house. Perched on a hill above beautiful Playa San Josecito. 5 minute walk to the beach, 1 1/2 hour hike to Corcovado Park, the jewel of the Osa Peninsula! Gorgeous sunsets and view of Cano Island right from the balcony! Totally private …see more

from $225 / night

$1575 / week

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from $225 / night

(7) Excellent 

20

Vacation home with swimming pool in Golfito

Osa Peninsula / Golfito

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Golfito is located in the historic "Zona Americana" section of Golfito. The house was originally built by United Fruit Company as part of the housing provided to their executive management. This gated home sits on a one acre lot and includes a pool, rancho and beau …see more

from $375 / night

$2625 / week

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Responds fast!
avg. 3 hours 18 minutes

from $375 / night

11

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
This is perfect with sea view in Drake Bay for those who love the ocean view and tranquility. The house is 80 square meters and has a deck of 6×8 meters so you have enough space for your convenience. Home Features Overlooking the Pacific Ocean 5 single beds Kitchen Fu …see more

from $260 / night

$1820 / week

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Responds fast!
avg. 3 hours 23 minutes

from $260 / night

(2) Very Good 

18

Golfito Vacation home rental

Osa Peninsula / Golfito

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Beautiful Home with two room available with bath and shower each one. All utilities include!! The owner lives on main floor, recently built and luxiourious.. Located in Golfito adjacent to four star hotel with fine dining and bar just steps away. Neighborhood …see more

from $170 / night

$851 / week

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Responds fast!
avg. 3 hours 40 minutes

from $170 / night

(2) Very Good 

24

Home accommodation in Drake Bay

Osa Peninsula / Drake Bay

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
This is your chance to completely escape the monotonous grind of everyday life and rejuvenate your body and mind with a healthy dose of natural beauty, active adventure, rustic luxury, and cultural authenticity. All five senses will be on full alert here…each one contri …see more

from $99 / night

$600 - $1630 / week

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from $99 / night

(6) Excellent 

14

Carate Vacation home rental

Corcovado National Park / Carate

2 7 5 nights min

  • 2 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Suitable for children age 5+
Playa Lapa is a privately owned ocean front residence in remote Carate, Costa Rica, only two miles from the Corcovado National Park. The Casa is tucked deep in a grove of lowland palms, right on the beach facing the Pacific Ocean and insulated from the rest of the worl …see more

from $210 / night

$1470 - $1995 / week

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Responds fast!
avg. 1 hour 42 minutes

from $210 / night

(29) Excellent 

39

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
This is the perfect location for an exotic honeymoon, a bird watching tour, a yoga retreat or a playful base for an unforgettable family vacation. Leave the real world behind and let your inner child emerge. The home is in Cabo Matapalo, on the Osa Peninsula in Costa Ri …see more

from $250 / night

$1750 - $4500 / week

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from $250 / night

29

Home accommodation in Corcovado National Park

Osa Peninsula / Corcovado National Park

4 15 1 night min

  • 4 bedrooms
  • Sleeps 15
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Welcome to The Beach House in Puerto Jimenez, Costa Rica on the Osa Peninsula which is one of the most bio-diverse places on the planet. With nature all around the area boasts a wealth of wild life. The Beach House is located in front of a calm swimming beach about a 15 …see more

from $250 / night

$1500 / week

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from $250 / night

29

Vacation beach hut in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

6 2 1 night min

  • 6 bedrooms
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.1 mi
  • Child friendly
  • Pet friendly
Camping accommodations include camping on the beach, or on the grass just fifty steps inland. Includes tent, air mattress, pillows, sheets and towels. We have basic facilities (outdoor toilet, sink & shower) for your comfort there, as well as a grill, outdoor kitchen an …see more

from $35 / night

$225 / week

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from $35 / night

(2) Excellent 

6

Vacation home rental

Osa Peninsula / Drake Bay

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Sonia's house is on the beach front portion of the Amaya family property but faces the rainforest and a small private spring fed waterfall. You can see three of the four species of monkeys that reside in Costa Rica from the front porch or private covered gazebo (they co …see more

from $270 / night

$1890 / week

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Responds fast!
avg. 2 hours 9 minutes

from $270 / night

(1) Excellent 

14

Vacation home rental

Osa Peninsula / Puerto Jimenez

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Simple yet comfortable tropical screened home with an open style floor plan inside, large patio with hammocks outside. 110 yds from the pristine Golfo Dulce, ocean view thru trees, this rental offers access to jungle and sea adventures. …see more

from $99 / night

$693 / week

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from $99 / night

(7) Excellent 

7

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Open air living with all the comforts of home. Jungle luxury living if you will. Master bedroom with king size bed and large, spacious private bathroom. Second bedroom is dorm style with custom bunk bed system with playroom and easy access to the second bathroom. Large …see more

from $225 / night

$750 / week

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from $225 / night

72

Vacation cottage in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
When was the last time you thought that Life was way too busy? Wouldn't it be nice to take a Time-Out from the "fast-track" and experience an alternative. Something Basic, Simple yet Elegant and which offers complete Freedom to be who you really are or maybe even who yo …see more

from $79 / night

$500 - $599 / week

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Responds fast!
avg. 2 hours 9 minutes

from $79 / night

(1) Excellent 

32

Vacation home with shared pool in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Beautiful "Open Air" two-story safari home with 3 private bedrooms that sleep 6. There are 2 hanging Hammocks in main central room for 2 additional guests if needed. Property is privately situated at the end of Matapalo Beach rd. on a pristine secluded beach surrounded …see more

from $129 / night

$895 - $1595 / week

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from $129 / night

(2) Excellent 

5

Shepherds hut rental in Drake Bay

Osa Peninsula / Drake Bay

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
We are a lovely Argentine-Tico Family. We have lived in Costa Rica for the last 10 years, in a beautiful remote area in Drake Bay, right in the tropical rainforest- The place is very confortable: -Modern-rainforest cabina with kichenette. - Balcony with hammock and for …see more

from $100 / night

$700 / week

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from $100 / night

(1) Very Good 

16

Home rental in Puerto Jimenez with shared pool

Osa Peninsula / Puerto Jimenez

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Playa Sombrero has an open construction style that allows for a steady ocean breeze throughout the living space and provides both ocean and lush mountain views. Upstairs has a large floor plan with a beautiful hardwood floor and a thatched-roof ceiling. This room …see more

from $180 / night

$1200 - $1800 / week

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from $180 / night

(14) Excellent 

19

Puerto Jimenez Vacation home rental

Osa Peninsula / Puerto Jimenez

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets
A towering three-story treehouse set amid the jungle canopy, Punta Jaguar is the perfect base for your adventures on Costa Rica’s Osa Peninsula. Built with unique, breathtaking views of the ocean and jungle, Punta Jaguar is alive with the myriad species of birds and ani …see more

from $300 / night

$2450 / week

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from $300 / night

8

Home rental in Puerto Jimenez with indoor pool

Osa Peninsula / Puerto Jimenez

6 9 Min stay varies

  • 6 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Puerto Jimenez Vacation rentals just north of pristine beaches. It’s almost like having a resort all to yourselves since this is a private reserve. No need to decide if you want a Costa Rica beach house rental or rain forest rental - here at Osa Springs Luxury Resort -Y …see more

from $235 / night

$1250 - $4045 / week

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from $235 / night

(1) Excellent 

34

Cabo Matapalo Vacation home rental

Osa Peninsula / Cabo Matapalo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Child friendly
Visitors repeatedly say that Casa Linda is exceptional. So take a walk on the wild side! This off-grid Costa Rica beach rental offers nature lovers, surfers and fishermen an ideal vacation. It sits on four acres of beautiful beachfront and world-class SUP surfer's dream …see more

from $125 / night

$851 - $2766 / week

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from $125 / night

42

Puerto Jimenez Vacation home rental

Osa Peninsula / Puerto Jimenez

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
The Toucan Hut is the junior suite at Casa Manglar Guest House. It's aptly named because many days of the year one may view Toucans from the windows of the room. Double bed with A/C, En-Suite Bath and full walk-in Closet and Wifi. The house is extraordinary in it's se …see more

from $79 / night

$500 - $599 / week

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Responds fast!
avg. 2 hours 9 minutes

from $79 / night

1